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United States Patent (19) (11) 4,138,477 Gaffar 45 Feb United States Patent (19) (11) 4,138,477 Gaffar 45 Feb. 6, 1979 (54) COMPOSITION TO CONTROL MOUTH 3,956,480 5/1976 Dichter .................................. 424/49 ODOR 4,022,880 5/1977 Vinson ................................... 424/49 75) Inventor: Maria Corazon S. Gaffar, Somerset, OTHER PUBLICATIONS Websters Third New International Dictionary (un (73) Assignee: Colgate Palmolive Company, New abridged) 1963, p. 2174, "Sorbic Acid and/or Sorbate.” York, N.Y. Crisp et al., "Zinc Polycarboxylate Cements:' J. Dent res. 1976, 55, 2, pp. 299-308. (21) Appl. No.: 691,262 Begala et al., J. of Physical Chem., (1972), 76, 2, pp. 22 Filed: May 28, 1976 254-260. 51) Int. Cl.’......................... A61K 7/16; A61K 7/18; Primary Examiner-Shep K. Rose A61K9/68; A61K 31/315 Attorney, Agent, or Firm-Robert L. Stone; Murray M. 52 U.S. C. ........................................ 424/52; 424/48; Grill; Herbert S. Sylvester 424/49; 424/56; 424/78; 424/81; 424/83; 424/145; 424/289 57 ABSTRACT 58) Field of Search .................................... 424/48-58, A novel composition to prevent and control mouth 424/78-83, 145, 289 odor, which is also effective in preventing calculus, (56) References Cited plaque, caries and periodontal disease containing as the U.S. PATENT DOCUMENTS essential agent, a zinc-polymer combination formed by the reaction or interaction of a zinc compound with an 1,593,485 7/1926 Crosnier ................................. 424/76 anionic polymer containing carboxylic, sulfonic and/or 3,070,510 12/1962 Cooley .................. ... 424/52 phosphonic acid radicals. 3,429,963 2/1969 Shedlovsky et al ... 424/56 3,943,267 3/1976 Randol ................... ... 424/49 10 Claims, No Drawings 4,138,477 1. 2 and oral mucosa, thereby forming a reservoir of zinc COMPOSITION TO CONTROL MOUTH ODOR ions capable of being gradually released with time into This invention relates to novel oral formulations the oral environment. comprising a combination of a zinc compound and an Accordingly, it has now been found that mouth odor anionic polymer as an effective agent against mouth can be controlled by treating the oral cavity with a odor, plaque, calculus and periodontal disease. combination of a zinc compound and an anionic poly The prior art is replete with oral compositions con mer. Said zinc-polymer combinations provide both a taining zinc salts such as zinc chloride, zinc iodide, zinc means of attachment to the oral cavity as well as form a fluoride, zinc sulfide, zinc phenol sulfonate and the like reservoir of zinc ions which are gradually released over as antiseptic agents, and correctives of oral conditions 10 a protracted period of time as an effective means to such as pyorrhea. Zinc chloride has commonly been combat mouth odor, plaque, calculus, and periodontal used in oral formulations for its astringency properties. disease. In addition, the zinc-polymer combinations Zinc phenol sulfonate has been utilized in the prior art decrease the high astringency which is characteristic of dentifrice compositions as an anti-plaque and anti-cal zinc ions, thereby leaving a more pleasant taste in the culus agent as well as an odor inhibitor of fermentation 15 mouth. and putrefaction which occurs in the oral cavity. These It has been ascertained through equilibrium dialysis soluble zinc salts have the dual disadvantage of leaving studies against water that the zinc ions are bound to the an unpleasant astringent taste in the mouth as well as anionic polymer and are slowly released with time as having short-lived efficacy against plaque, calculus and clearly indicated by the results in Table I, wherein as an odor inhibitor. 20 0.025% zinc oxide plus 2% of a copolymer of vinyl Sparingly soluble zinc salts such as zinc citrate, zinc methyl ether and maleic anhydride having a molecular C14-alkyl maleate, zinc benzoate, zinc caproate, zinc weight of 250,000 (Gantrez 119) was tested against zinc carbonate, zinc citrate, etc. have been used in dentifrice oxide per se. formulations to prolong the anti-calculus and anti plaque effectiveness of the zinc ions due to the slow 25 Table I dissolution of the zinc salts in the saliva. The sparingly Equilibrium Dialysis Studies soluble characteristic of these zinc salts promotes lon Rate of Dissociation gevity of action against plaque and calculus at the ex Compound 10 Min Hr 24 Hrs pense of initial or immediate efficacy. Zn2+ Gantrez 119 0. 0 53 The use of a zinc complex of a specific diketone as an 30 Znt? Hot 2 70 100 agent for combating tartar and tooth discoloration is '0.025% zinc oxide -- 2%. Gantrez 119; pH adjusted to 6.5 with 3N NHOH also known, as set forth in German Patent No. "0.025% zinc oxide + 1N HCl; pH adjusted to 6.5 with 3N NHOH 2,229,466. Thus, it is apparent that zinc compounds generally are known to have deodorizing properties as The above table clearly shows that no zinc was de well as efficacy against plaque, calculus and possibly 35 tected in the dialysate (outside membrane) after 10 min periodontal disease. utes, and after 1 hour of dialysis; and only 53% zinc was Also known is the use of a water soluble sodium salt found in the dialysate after 24 hours dialysis. Whereas, of a linear anionic polymer as an anti-calculus agent, as in the absence of the polymer, 21% zinc was detected in set forth in U.S. Pat. No. 3,429,963 to Shedlovsky. This the dialysate after only 10 minutes, 70% zinc was found patent discloses that the hydrolyzed copolymers and/or 40 after only 1 hour and 100% zinc was found in the dialy polymers prevent the deposition of calculus by means of sate after 24 hours dialysis. In the presence of saliva their calcium sequestration properties. However, there salts, the zinc ions are bound to the polymer and are is no suggestion in this patent, nor in any of the known even more gradually released with time, with only 7% prior art, that a combination of a zinc salt and an anionic zinc being detected in the dialysate after 24 hours. In polymer is unusually effective in preventing and con 45 contrast, in the absence of the polymer, the zinc is dia trolling mouth odor while simultaneously preventing lyzed out 7% after 10 minutes; 50% after 1 hour; and calculus, plaque, caries and periodontal disease. 100% after 24 hours. Accordingly, it is an object of this invention to pro The anionic polymers are well known in the art. vide an oral composition containing as the mouth odor Preferably, the polymer is one which is linear and inhibitor, the reaction product of a zinc salt with an 50 water-soluble. For example, it may be soluble in water, anionic polymer. when in its sodium or ammonium salt form, at least to Another object of instant invention is to provide an the extent of the concentration in which it is employed oral composition effective in inhibiting mouth odor (0.1% to 10%). See for instance the anionic polymeric over a protracted period of time. materials described in U.S. Pat. Nos. 2,984,639, Still another object of this invention is to provide an 55 3,325,402, 3,429,963, the article on "Polyelectrolytes' in oral composition effective in inhibiting plaque, calculus, Vol. 10 of Encyclopedia of Polymer Science pages 781 caries and periodontal disease. ff, particularly pages 781, 782 and 784 listing various It has been found, through radioisotope studies, that polyelectrolytes. The anionic polymers employed anionic polymers can be adsorbed onto oral surfaces. herein preferably containionizable carboxyl, sulfonic or Accordingly, an effective method of controlling mouth phosphonic groups. A preferred type of polymers has odor entails the use of an oral composition comprising a its ionic substituents on a polymer chain which is hydro zinc polymer salt or complex formed by combining zinc carbon preferably aliphatic hydrocarbon (e.g. a vinyl compounds with anionic polymers. The positively polymer). Typical of such anionic polymers are copoly charged zinc ions can react with the polymeric car mers of an unsaturated polybasic carboxylic acid or boxyl, sulfonic orphosphonic acid groups of the anionic 65 anhydride thereof (preferably dibasic and having 4 car polymers to form zinc-polymer combinations. In the bon atoms per molecule) and of an olefin having 2 or presence of excess acidic groups, the zinc-polymer com more carbon atoms per molecule; polyolefin sulfonates; binations adsorb onto the oral surfaces such as the teeth polyolefin phosphonates; and polyolefin phosphates, 4,138,477 3. 4. the olefin group containing 2 or more carbon atoms. to 1.5 mg/ml zinc may be mixed with the anionic poly Suitable examples include: mer. Examples of suitable zinc compounds that may be 1. A copolyrner of maleic anhydride with ethylene, or employed include: styrene, or isobutylene, or polymethyl vinyl ether, or polyethylvinyl ether, having recurring groups: 5 zinc acetate zinc isovalerate zinc acetylacetonate zinc D-lactate -X-CH-CH zinc ammonium sulfate zinc DL-lactate zinc benzoate zinc laurate zinc bromide zinc hexafluorosilicate COOM COOM zinc beryllium orthosilicate zinc methacrylate 10 zinc borate zinc molybdate wherein M and M1 are individually hydrogen, sodium, zinc butylphthalate zinc naphthenate zinc butylxanthate zinc octoate potassium or ammonium and may be the same or differ zinc caprylate zinc oleate ent, and X is ethylene, styrene, isobutylene, methylvinyl zinc carbonate zinc orthosphosphate zinc chloroanilate zinc phenolsulfonate ether, and ethylvinyl ether. zinc chlorate zinc pyridine-2-thiol-1-oxide 2. A polyacrylic acid and polyacrylates thereof hav- 15 zinc chromate zinc pyrophosphate ing recurring groups: zinc citrate zinc resinate zinc cyclohexanebutyrate zinc salicylate zinc chloride zinc sulfate zinc gallate zinc nitrate zinc fluoride zinc selenide -H-CH-H-CH zinc alpha-glucoheptonate zinc stearate COOM COOM 20 zinc gluconate zinc sulfanilate .
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