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Publication numberUS2772204 A
Publication typeGrant
Publication dateNov 27, 1956
Filing dateSep 13, 1954
Priority dateSep 13, 1954
Publication numberUS 2772204 A, US 2772204A, US-A-2772204, US2772204 A, US2772204A
InventorsKing William James
Original AssigneeColgate Palmolive Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Dental preparations containing higher aliphatic acyl sarcoside compounds
US 2772204 A
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Description  (OCR text may contain errors)

United States Patent DENTAL PREPARATIQNS CONTAINING HIGHER ALIPHATIC ACYL SARCOSIDE COMPOUNDS William James King, River Edge, N. assignor to C01- gate-Palmolive Company, Jersey City, N. 3., a corporation of Delaware v No Drawing. Application September 13, 1954,

erial No. 455,761

3 Claims. or. 167- 93) The present invention relates to dental preparations comprising certain higher aliphatic acyl sarcoside compounds. The instant application is a continuation-in-part of'co-pending applications, Serial No. 258,759 filed November 28, 1951, and Serial No. 271,864 filed February 15, 1952, now U. S. Patent No. 2,689,170 issued September 14, 1954.

Many commercial dental preparations have incorporated therein minor amounts of certain detergents such as soap to provide detersive and foaming characteristics.

According to the present invention, improved dental preparations may be prepared by the incorporation of a substantially saturated higher aliphatic acyl sarcoside compound containing 17-18 carbons in said acyl group.

Thus, these active ingredients comprise the stearoyl and heptadecanoyl amides of sarcosine compounds. These compounds may be employed in the form of the free acids or preferably as the Water-soluble salts thereof. Suitable salts are the alkali metal (e. g. sodium and potassium), ammonium, amine and alkylolamine (e. g. mono-, diand triethanolamine) salts and the like. Further specific examples are stearoyl sarcosine and its sodium and potassium salts, and heptadecanoyl sarcosine and its sodium and potassium salts. For convenience, herein, the terms sarcoside compound or sarcoside refer to such compounds having a free carboxylic group or the watersoluble salts thereof, unless further specified.

These amide compounds should be utilized in pure or substantially pure form. They should be substantially free from soap or similar higher fatty acid material which is formed in normal commercial methods of manufacture and which tends to neutralize or substantially reduce some of the special characteristics of the active ingredients. In usual practice, the amount of higher fatty acid material should be less than by weight of the amide compound and insuflicient to substantially adversely affect said amide, and preferably less than about 10% of said amide with optimum results at 0-5% fatty acid material. 7 1

These compounds may be produced in pure or substantially pure form by the condensation of the corresponding fatty acylating substance, such as stearic acid chloride (or equivalent substantially saturated fatty acid -mixtures consisting essentially of the stearic acid chloride), with sarcosine in an alkaline medium, as described in co-pending application, S. N. 271,864, now U. S..Patent No. 2,689,170. -It is believed that the heptadecanoyl sarcoside compounds are specifically novel, and therefore the process will be illustrated with particular reference thereto. Normal heptadecanoic acid is treated with phosphorus trichloride to obtain the corresponding acid chloride. The heptadecanoyl acid chloride is condensed with sarcosine (20% molar excess) at a pH of about 10.5 in presence of sodium hydroxide and at room temperature to form the corresponding sodium heptadecanoyl sarcoside. This product is acidified to a pH of 2, extracted with ethyl ether, washed with 5% sulfuric acid and water, and dried. The resulting heptadecanoyl sarcosine beneficial characteristics of particular desirability in is crystallized from Skellysolve E, neutralized with alcoholic sodium hydroxide and re-crystallized from alco-v hol. Analysis of the sodium salt shows that it has a melting point of 143.5-144" C. and a neutral equivalent of 344 with less than 1% soap content. The heptadecanoyl sarcosine compound has a melting point of 6970 C. The other soluble salts, as indicated above, are formed similarly by neutralization with the desired base, such as potassium hydroxide or ethanolamine to form the corresponding salts.

These compounds exhibit many highly unusual and dental preparations. Among the unusual properties is their anti-bacterial power on the oral flora (the complex mixture of micro-organisms normally present in the mouth). These compounds exhibit a superior inhibiting effect on bacterial growth and the production of "acid from fermentable carbohydrates by these micro-organisms found in saliva. This superior inhibiting effect may be illustrated by the Snyder dilution test which is known in the art. In accordance with this test, a very small portion of these compounds may be added to Snyder tubes containing a nutrient dextrose agar with brom-cresol green indicator which had been inoculated previously with saliva. After 72 hours incubation at 37 C., the tubes containing these compounds are still green in color indicating marked inhibition of 'acid production with no evidence of bacterial growth. As a control, similar tubes without the addition of these compounds have turned yellow after only 24 hours incubation indicative of rapid and substantial acid formation, with the formation of bacterial colonies. For example, the minimum amount of sodium stearoyl sarcoside which is necessary to maintain a predominantly green color for 72 hours in the Snyder test is an amount corresponding to about 50 milligrams per cc. of the saliva normally turning the control tubes yellow in 24 hours. As indicative of the specificity of action with respect to the chemical structure of these active ingredients, it has been found that such structurally-similar materials as sodium stearoyl glycide and sodium oleyl sarcoside are not equivalents but are markedly inferior in anti-bacterial activity against the oral flora and inhibition of acid formation.

It has been found also that these active ingredients have the property of reducing the solubility of tooth enamel in acid to a marked degree. Such laboratory tests for evaluating the reductionin enamel solubility are known. Data obtained in such tests indicate that both sodium stearoyl and heptadecanoyl sarcosides exhibit significant effects in this respect whereas unsaturated compounds such as sodium oleyl and elaidyl sarcosides are markedly inferior.

These active ingredients may be utilized in any preparation designed for application to the oral cavity which are referred to herein as dental preparations. Such dental preparations include suitable toothpaste and dental creams, tooth powders, liquid dentifrices, mouth washes or rinses, lozenges, tablets,"chewing gum, dental floss and the like. These preparations may contain various adjuvant materials in suitable amounts provided the same do not substantially adversely afiect the desired results. Any suitable amount of these compounds may be incorporated in the dental preparation. The specific amount will vary, naturally, depending upon the specific type of preparation and the specific effects desired, but will generally be a minor amount of the composition, such as usually at least about 0.05 and up to about 10% by Weight. In the case of dentifrices such as dental creams, it is preferred to use an amount from about 0.25 to about 5% by weight.

Any suitable practically water-insoluble polishing agent may be admixed with these'active' ingredients in the preprelatively large number of such materials known in the art including, for example, calcium carbonate, dicalcium phosphate; tricalcium phosphate, insoluble sodium metaphosp a a u inum byes-s i s, mag sium c onat andibentonite. ,I-t ispreferred to, use the water-insoluble calcium and magnesium salts, and, more particularly cal cium.:carbonate and/or; a :caiei-um' phosphate. In gen- QlfiL-Ihflsfi polishing agents comprise amajor .proportien by weight of thesolid ingredients and aid in cleansing the mouth: l. .7

In h p e a -Q eq e dei it s svf ficient to mechanically admin the Mar -ious' ingredients.

In dental cream formulations, the liquids, and sol-ids should. necessarily be proportioned to form a creamy mass of desired consistency which is veX-trudible from a 7 collapsible aluminum or lead tube. In general, the liquids in the dental .creamwill eomprise chiefly water, glycerine, sorbitol, propylene glycol andrthe like, including suitable' mixtures thereof. .It is usually-advantageous to use a mixture of both water and a humectant or binder such ness even after aging for long periods oftime. l Various suitable stabilizing agentsare-calcium andmagnesium sequestering agents such as the water-soluble inorganic polyphosphate salts; Examples thereof are the alkali metal salts of 'pyrophosphoric, tripol-yphosphorie or tetraphosphoric' acids. 7 Specific materials are tetrasodium pyrophosphate, -,disodiu m ,diacid pyrophosphate,

sodium and potassium tripolyphosphate, hexasodium .tetraphosphate and sodium henamctaphosphate salts, with the pyrophosphates preferred; Soluble sodium and potassium metaphosphate.maydaeused also. Other suitalkali metal and preferably-sodium salts. of ethylene diamine tetraacetic :acid and'citric acid. These stabilizing agents may be employed inzanysuitable amount depending upon the specific formulation but will usuallylae .up to 'pre ly t am-018. by w ie o the composition.

aration of various. dentifice compositions. There is a 7 able stabilizing agents are .ch la i lg a n s h as the Other adjuyant materials are usually incorporated in 7 7 may vary depending on the mouth effect desired, such weight; Liguiddentifrices are also included, such produ t ellc ntain n dd tio m i agin9u m terial ;and ioptionall y combined with small amounts of 7 reli i as sigly r nc andit e like- An her bodiment is hewing su whi h wi l con ain :mi QIj I-u efiective amounts of these active ingredients incorp:orated in t e s m a e such as ch .QI o her natural or sy thetic rubber and gum-like materials.

Sodium stearoyl-sarcosidei;

The pH of the final formulations of the present invention is variable and, therefore, the products may have any suitable pH value in solution compatible with the stability of the materials. Where reference is made to pH values it has reference to the pH as determined on'a liquidproduct 'per se, and in the .case of a dental cream or with optimum desired eifects at a' substantially neutral pH value in solution, e. -g., about 6 to 8.

The following specific examples are further illustrative" of the nature of the present invention, but it is to be understood that the invention is notlimited thereto. The

preparations may be prepared in the'usual manner and all amounts of the various ingredients are by Weightunless otherwise specified. I V V W Example'l Dntal c eam 7 Percent the balance consisting essentially of soluble saccharin,

flavor and preservatives.

hExai rtple'llir-efoo th powder 7 1 V Percent 'Sodiumpheptadecandly sarcosi'de 3.0 Calcium carbonate a 25:0 Dicalcium phosphate..dihydrate "70.0 Saccharin, soluble L.. a;;n; '0i2 Flavor'n V "128 77 7 100.0 Examplelllsa-Mouth wash 7 77 V V Percent Potassium stearoyl sarcoside; -O .1-;'0.2 Ethyl alcohol V i i i 7' i "10.0 Flavor V 7 w 7 V 0:15 'Saccharin, soluble a (X0 1. Distilled water Q ;Q -L Balance Example IV. Che.wing g um 7 1 rcen .Sodium .stearqyl, arc s 0.5 Gum base, e. g. ch c 7, 20.1) Sucrose 60.0 Corn syrup", 1 8.5 Flavor 3139 7 7 7 7 V 5 109.0 Example :V.-+Liquid dantirifice V 7 7 7 7 7 7 7 Percent Sodium .stearoyl sarcoside' 2.0 :Sodium ,carbonymethylCellulose..- 2:0 Flavor 0.5 Distilled wat r Balance .Although the present invention been described reference :to particular embodiments and examples, it' I will be apparent to those skilled in that Yart that. lvaria lions a m difis as 9 th s n entis n e made sl thateguivalents can be substituted therefor without parting ,from the principles and true spirit of in- ,Ha ng' us' ;d isd th was. w i .clai ed is. l i v V .i A en a Pre a ion a mnp i s a ar q ds pound selected from the group consisting of N-heptadecanoyl and N-strearoyl sarcoside compounds having less than about 15% based on the weight of said satcoside of higher fatty acid material, the amount of said material being insufiicient to adversely afiect said sarcoside.

2. A dentifrice comprising a polishing material and a minor amount of sodium N-heptadecanoyl sarcoside hav ing less than about 10% of higher fatty acid material based on the weight of sarcoside.

3. A dentifrice comprising a polishing material and a minor amount of sodium N-stearoyl sarcoside having less than about 10% of higher fatty acid material based on the weight of sarcoside.

References Cited in the file of this patent UNITED STATES PATENTS Dreyfus Dec. 15, 1936 Bird Oct. 25, 1949 King Sept. 14, 1954 FOREIGN PATENTS Germany Sept. 18, 1936 Germany Apr. 27, 1939 Great Britain Nov. 3, 1936 Great Britain Dec. 28, 1936 Great Britain Feb. 15, 1937 France July 6, 1935 France Dec. 26, 1935

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2063987 *Aug 22, 1932Dec 15, 1936Dreyfus HenryAmino carboxylic acid condensation products and process of making them
US2486249 *Jul 19, 1947Oct 25, 1949Nat Aluminate CorpAcylamino-nu-substituted amides
US2689170 *Feb 15, 1952Sep 14, 1954Colgate Palmolive CoOral preparation for inhibition of dental caries
DE635522C *May 16, 1930Sep 18, 1936Ig Farbenindustrie AgWasch-, Netz-, Dispergier- und Egalisiermittel
DE675837C *Jun 12, 1932May 22, 1939Ig Farbenindustrie AgZahnreinigungsmittel
FR787819A * Title not available
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GB461328A * Title not available
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3932603 *May 28, 1971Jan 13, 1976General Foods CorporationAntimicrobial against streptococci
US4088752 *Jun 2, 1975May 9, 1978Gaba AgOral composition for plaque and caries inhibition
US4122162 *Jun 14, 1976Oct 24, 1978Muehlemann Hans RSalt of an oxo-acid of phosphorus with an organic amine base
US4545979 *Sep 26, 1984Oct 8, 1985Warner-Lambert CompanyDental hygiene compositions
US4550018 *Sep 26, 1984Oct 29, 1985Warner-Lambert CompanyAntiplaque mouthwash, antiseptic containing a pure alkali metal salt of lauryl sulfate
US5017364 *Oct 17, 1989May 21, 1991Ajinomoto Co., Inc.N-acylglutamate, no aftertast with orange juice
US5266306 *May 23, 1991Nov 30, 1993Sunstar Kabushiki KaishaCetylpyridinium chloride and n-acyl basic amino acid alkyl ester; bactericide, anticaries, antiplaque agents
Classifications
U.S. Classification424/48, 424/DIG.600, 424/54, 554/63
International ClassificationA61K8/44, A61Q11/00
Cooperative ClassificationY10S424/06, A61Q11/00, A61K8/44
European ClassificationA61K8/44, A61Q11/00