Tartar control denture adhesive compositions

Description of the invention

The present invention relates to an adhesive denture composition.

Conventional removable dental prostheses, dental prosthesis plates and the like, include teeth mounted on a suitable plate or substrate. Denture stabilizers are used to fill gaps between dentures and gums or tissues. Before placing the prosthesis in the oral cavity, a prosthesis stabilizer is applied to the surface of the prosthesis plate, which, to ensure a perfect fit, should evenly contact the gums and mucous tissues. Denture stabilizers are formulated not only in terms of their adhesion properties, but also to create a kind of cushion or pad between the denture and the gums or tissues, thereby achieving a secure positioning of the denture in the oral cavity.

Much effort has been made over the years to develop improved adhesive denture compositions. Both synthetic and natural polymers and resins have been used, individually, in combination with each other and in combination with various adhesives and other materials, in an attempt to improve adhesion and reduce the flow of adhesive from under the denture plate and reduce dirt and difficulties removing adhesive residues from the mouth and denture dental. For example, alkyl vinyl ether-maleic acid copolymers are known to provide good adhesion in adhesive denture compositions. Such disclosures are contained in US Patent Nos. 3,003,988 (Germann et al.) Issued October 10, 1961; 4,980,391, Kumar et al. Issued Dec. 25, 1990; 5,073,604, Holeva et al. Issued Dec. 17, 1991; 5,525,652 (Clarke) issued June 11, 1996; 5,340,918 (Kittrell et al.) Filed August 23, 1994. and 5,830,933 (Synodis et al.) on November 3, 1998.

In addition to adhesion, it is desirable that adhesive denture compositions exhibit anti-calculus or tartar effect, which is particularly important for those denture wearers who still have some natural teeth. Tartar is a deposit that forms on the surface of the teeth. Fully developed tartar consists of an inorganic part, which is largely calcium phosphate, formed into a hydroxyapatite crystal lattice structure similar to that of bone, enamel and dentin. An organic portion is also present, consisting of exfoliated epithelial cells, leukocytes, salivary sediment, food debris, and microbes.

It is generally known that certain polyphosphates are effective anti-calculus agents when delivered into the oral cavity by incorporating aqueous compositions such as dentifrices or mouthwashes. For example, U.S. Patent 5,096,699 (Gaffar et al.) Issued March 17, 1992, assigned to Colgate, describes dentifrice and mouth rinse compositions containing azacycloalkane-2,2-diphosphonic acid (AAP) and salts thereof, and synthetic polymeric anionic polycarboxylate (SAPP). In addition, U.S. Patent No. 4,913,895 (Miyake et al.) Issued April 3, 1990, discloses dentifrice and mouth rinse compositions with selected polyphosphates and menthol, anethole, or mixtures thereof. However, these publications disclose the delivery of polyphosphates only in aqueous dentifrice and mouth rinse compositions, where delivery is also dependent, at least in part, on brushing or rinsing the mouth. The prior art therefore does not provide any suggestion that anti-tartar agents may be available and delivered in sufficient amounts to achieve anti-tartar benefits when incorporated into non-aqueous compositions also containing tackifying ingredients.

Despite the above-discussed and other technologies as well, there is still a need for denture stabilizing compositions that provide the wearer of the dentures with both improved adhesion and anti-calculus. According to the invention, adhesive denture compositions comprising an adhesive denture component in association with an anti-tartar agent provide the benefit of reducing tartar deposit while providing excellent denture adhesion.

Accordingly, the invention relates to a non-aqueous adhesive denture composition based on alkyl vinyl ether-maleic acid or anhydride copolymers and polyphosphates containing

a) 20-50% by weight, based on the weight of the composition, of a denture adhesive component selected from the group consisting of salts of an alkyl vinyl ether-maleic acid or anhydride copolymer, salts of alkyl vinyl ether, maleic acid or anhydride and isobutylene terpolymers, and mixtures thereof;

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b) 4.5-40% by weight, based on the weight of the composition, of an anti-tartar selected from the group consisting of polyphosphates and their salts, and mixtures thereof; and

c) a non-aqueous carrier of a denture adhesive component selected from

- a non-aqueous carrier substance selected from the group consisting of liquid paraffin, petroleum jelly, mineral oil, glycerin, natural and synthetic oils, fats, silicone and silicone derivatives, polyvinyl acetate, natural and synthetic waxes, vegetable oil waxes, vegetable oils and mixtures thereof; preferably liquid paraffin, petroleum jelly, mineral oil, glycerin and mixtures thereof; and

- a non-adhesive self-supporting layer selected from the group consisting of polyester, polypropylene, nylon, rayon, cellulose acetate, non-stick cellulose derivatives, fabric, fleece, paper, plastic, leather, synthetic fibers, natural fibers and mixtures thereof.

Preferably the composition according to the invention comprises a salt of an alkyl vinyl ether-maleic acid copolymer or maleic anhydride copolymer as the denture adhesive component, the salt containing a salt-forming cationic group containing a cation selected from strontium, zinc, iron, magnesium, calcium, sodium and mixtures thereof. .

More preferably, the composition of the invention comprises as an adhesive component for a dental prosthesis a salt of an alkyl vinyl ether-maleic anhydride copolymer which is a mixed salt containing a cationic salt-forming group containing two or more cations selected from strontium, zinc, iron, magnesium, calcium, sodium and mixtures thereof.

Preferably, the composition according to the invention comprises an alkyl vinyl ether-maleic acid copolymer salt having a free acid group content of 36-60% as the denture adhesive component.

Preferably, the composition of the invention comprises an anticalculus agent selected from the group consisting of alkali metal pyrophosphates, di-, tri- and monopotassium or sodium pyrophosphates, di-alkali metal pyrophosphates, alkali tetrametal pyrophosphates, and mixtures thereof; preferably trisodium pyrophosphate, disodium dihydrogen pyrophosphate (Na2H2P2O7), dipotassium pyrophosphate, tetrasodium pyrophosphate (Na4P2O7), tetrapotassium pyrophosphate (K4P2O7) and mixtures thereof.

Furthermore, it is preferred that the composition of the invention comprises hexametaphosphate as the anti-calculus agent.

A detailed description of the essential and optional ingredients used in the invention is provided below.

Definitions

The term "anti-calculus or" anti-calculus agent as used herein means a substance that is effective in reducing, combating, inhibiting, preventing and / or minimizing the formation of mineral deposits (e.g., calcium phosphate) associated with the formation of calculus or tartar.

The term "AVE / MA" as used herein refers to an alkyl vinyl ether-maleic acid or anhydride copolymer. The term "AVE / MA / IB" refers to terpolymers of alkyl vinyl ether, maleic acid or anhydride and isobutylene. The term "mixed polymer salts or" mixed salts as used herein refers to an AVE / MA salt and / or an AVE / MA / IB salt in which at least 2 different cations are mixed with each other or with other salts in the same polymer.

As used herein, the term "free acid groups or component" FA refers to either the unreacted carboxyl groups (-COOH) of the AVE / MA and / or AVE / MA / IB copolymer plus any other monovalent cations of the carboxyl groups (e.g. COONa) of the polymer. Monovalent cations include those of group IA elements such as sodium, potassium, hydrogen, etc. The term "free acid group preferably refers to unreacted (-COOH) AVE / MA and / or AVE / MA / IB carboxyl groups plus sodium and potassium cations. More preferably, the term "free acidic group" refers only to unreacted carboxyl (-COOH) groups in AVE / MA and / or AVE / MA / IB.

The percentages reported herein with respect to the cationic groups of the salts of the alkyl vinyl ether-maleic acid or anhydride copolymers are defined as the stoichiometric percentage of the total amount of initial carboxyl groups reacted on the polymer.

Unless otherwise stated, all other percentages are percentages by weight of the composition.

Adhesive components for a dental prosthesis

The composition according to the invention comprises the above-defined denture adhesive in an amount of 20-50% by weight of the composition. In one embodiment of the invention, the composition comprises

The above-defined adhesive component for a dental prosthesis in an amount of at least 30% by weight of the composition.

"Adhesive components for a dental prosthesis are AVE / MA salts, AVE / MA / IB salts, and mixtures thereof.

Alkyl vinyl ether-maleic acid or anhydride copolymer.

In one embodiment of the invention, the denture adhesive is AVE / MA salts. The alkyl vinyl ether-maleic acid copolymer contains or consists essentially of repeating structural units:

(AND)

OR

I —CH — CH — CH — CH ² II o = cc = o II

HO OH

Where R is alkyl, preferably C1-C5-alkyl, n is an integer greater than one to denote the number of repeating structural units in the polymer molecule.

In one embodiment, the adhesive component is AVE / MA salts, preferably AVE / MA mixed salts, wherein the polymer comprises a cationic salt moiety containing cations selected from the group consisting of group IA and group 2A cations of the periodic table, yttrium, titanium, zirconium, vanadium, chromium, manganese, iron, nickel, copper, zinc, boron, aluminum, and mixtures thereof. In another embodiment, the adhesive component is an AVE / MA mixed salt, said salt containing a salt-forming cationic group containing cations selected from the group consisting of strontium, zinc, iron, boron, aluminum, vanadium, chromium, manganese, nickel, copper, yttrium. , titanium, magnesium, calcium, sodium, and mixtures thereof, and in yet another embodiment the cations are selected from the group consisting of strontium, zinc, iron, magnesium, calcium, sodium, and mixtures thereof.

AVE / MA contains a cationic salt moiety containing about 5 - 50%, in another embodiment about 10 - 40%, and in yet another embodiment about 10 - 35% (total initial number of carboxyl groups reacted) of zinc cations. The zinc cations may be mixed with other cations selected from the group consisting of about 5 - 65%, preferably about 10 - 60% strontium cations, about 0.001 - 2.5%, preferably about 0.01 - 2%, iron, boron, aluminum cations. , vanadium, chromium, manganese, nickel, copper, yttrium and / or titanium, about 5-65%, preferably about 15-50%, of calcium and / or magnesium cations.

AVE / MA and its salts and AVE / MA / IB and its salts are also described in US Patent Nos. 5,073,604 (Holeva et al.) Issued 12/17/91; 5,525,652, Clarke et al. Issued Jun. 11, 1996; 4,758,630 (Shah et al.) Issued Jul 19, 1988; 5,304,616, Rajaiah et al. Issued April 19, 1994; 5,424,058 (Rajaiah) Jun 13, 1995; 5124058 (Rajaiah et al.) On 6/13.95; 4,758,630 (Shah et al.) Issued Jul 19, 1988; 5,830,933, Synodis et al. Issued Nov. 3, 1998; 2,047,398, Voss et al. Issued Jul 14, 1936; 3003988 (Germann et al.) October 10, 1961; 5,880,172, Rajaiah et al. Issued Mar. 9, 1999; 5,900,470, Prosise et al., Issued 5/4/99; 5,037,924 (Tazi et al.) Issued 8/6/91; 5,082,913 (Tazi et al.) From 01/21/92. AVE / MA salts are also described in pending P&G Patent Applications Nos. 06/152158 (Rajaiah et al.) Filed September 2, 1999; 60/129164, Rajaiah et al. Issued April 14, 1999; 60/129162, Rajaiah et al. Issued April 14, 1999; 60/152122, Rajaiah et al. Issued Sep. 2, 1999; 09/291554 (Rajaiah et al.) Filed April 14, 1999; 09/389209 (Rajaiah et al.) Filed September 2, 1999 and 09/389210 (Rajaiah et al.) Filed September 2, 1999.

In one embodiment, the free acid content level of the AVE / MA or AVE / MA / IB salts is at least 36%, in another embodiment it is 36-60%, and in yet another embodiment of the invention 40-55% of the total original amount of carboxyl groups of the copolymer or terpolymer.

The specific viscosity of the starting acid copolymer or anhydride copolymer is about

1.2-14, measured preferably in a 1% (w / v) solution in MEK (methyl ethyl ketone) at 25 ° C. Other methods and solvents can be used to measure the specific viscosity, such as a 1% (w / v) solution in DMF (dimethylformamide) at 25 ° C and a 1% (w / v) solution in 2-butanone in 25 ° C. ° C.

Suitable AVE / MA copolymers can be made by well-known methods, see, e.g., U.S. Patent Nos. 2,782,182 and 2,047,398.

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The subject salt polymers can be prepared by reaction in an aqueous medium of an acidic or anhydride polymer with at least one salt cation forming compound such as described above having groups conventionally reacting with a carboxylic acid such as e.g. hydroxide, oxide, acetate, halide, lactate and the like. In one embodiment of the invention, zinc oxide, strontium carbonate, iron sulfate n-hydrate, etc. are used.

Ions that form toxic, irritating or contaminating by-products should be avoided, or special precautions and procedures should be taken to remove such by-products from the final polymer salt product. The particular compound used should be substantially pure to ensure obtaining a substantially pure salt of the polymer as the end product.

The salt polymer can be prepared by mixing the salt (sodium hydroxide, zinc oxide, strontium carbonate, ferric sulfate n-hydrate, calcium hydroxide and / or magnesium oxide, etc.) in an aqueous slurry. This mixture is combined with a powdered copolymer of alkyl vinyl ether, acid or maleic anhydride in the form of a slurry, in an amount sufficient to achieve the desired cation content in the end product. The process is carried out at room temperature and the slurry is then slowly heated to 70-95 ° C with constant vigorous stirring to prevent local precipitation of the cationic salt of the polymer. Stirring is continued to ensure complete reaction of the salt-forming compound with the copolymer.

Alternatively, the AVE / MA copolymer is hydrolyzed and neutralized in an aqueous mixture or suspension of one or more divalent and / or monovalent metal bases by heating to a temperature of about 45-100 ° C.

In each of the above methods, the resulting slurry or solution is transferred to shallow stainless steel drying trays and placed in a mechanically forced air drying oven at 60-70 ° C for sufficient time to evaporate the reaction medium (water) and remove the water. from copolymer (about 18 - 24 hours). Alternatively, the resulting slurry or solution may be drum dried at 100-200 ° C using hot steam to evaporate the water and obtain the flake copolymer. After drying, the polymer forms brittle flakes that can be easily detached from the surfaces of the trays and drums and ground to a fine powder as desired to achieve satisfactory denture stabilizing properties. Processes for the preparation of these mixed AVE / MA polymer salts are further disclosed in U.S. Patent Nos. 5,073,604 (Holeva et al.) Issued December 17, 1991 and 5,872,161 (Liang et al.) Issued February 16, 1999.

Anti-tartar remedy

The composition according to the invention comprises at least one anti-tartar in an amount of 4.5-40% by weight of the composition, in another embodiment 4.5-25%, in still another embodiment

4.5 - 20%, and in yet another embodiment 5 - 15% by weight of the composition. An adhesive denture composition releases an effective amount of an anti-tartar agent. The anti-tartar agent should also be substantially compatible with the other ingredients of the composition.

The anti-calculus agent is selected from the group consisting of polyphosphates and their salts. In one embodiment, the salts are alkali metal salts. In another embodiment, the anticalculus agent is selected from the group consisting of polyphosphates and their salts, and mixtures thereof.

Polyphosphate

In one embodiment of the invention, the anti-tartar agent is polyphosphate. Generally, a polyphosphate is composed of two or more phosphate molecules, mainly arranged in a linear configuration, although some cyclic derivatives may be present. Linear polyphosphates correspond to the formula (XPO3) n, where n is about 2-125, with preferably n being greater than 4, X is e.g. sodium, potassium, etc. In the case of (XPO3) n with n at least 3, the polyphosphates are glassy. The counterions in these phosphates may be alkali metal, alkaline earth metal, ammonium, C2-C6-alkanolammonium ions, and mixtures thereof. Polyphosphates are generally used in fully or partially neutralized form as water-soluble alkali metal salts such as potassium, sodium and ammonium salts and mixtures thereof. Inorganic polyphosphate salts include alkali metal (e.g. sodium) tripolyphosphates, tetrapolyphosphates, e.g. . Polyphosphates larger than tetrapolyphosphates usually occur as glassy amorphous materials. In one embodiment, the polyphosphates are polyphosphates

Manufactured by FMC Corporation, commercially known as Sodaphos (n = 6), Hexaphos (n = 13) and Glass H (n = 21), and mixtures thereof. The source of polyphosphates is 4.5 - 40% by weight of the composition.

Phosphate sources are described in more detail in Kirk & Othmer, Encyclopedia of Chemical Technology, Fourth Edition, Vol. 18, Wiley-Interscience Publishers (1996), pp. 687-707.

In one embodiment, the polyphosphates are linear, "glassy polyphosphates having the formula:

XO (XPO3) nX where X is sodium or potassium and n is on average about 6-125.

In one embodiment, if n is 2 in any of the above formulas, the anticalculus content is 4.5-40%, in another embodiment 5-25%, in still another embodiment 8-15% by weight of the composition. Polyphosphates are disclosed in U.S. Patent No. 4,913,895.

Pyrophosphates

Useful pyrophosphates in the composition of the invention are alkali metal pyrophosphates, di-, tri- and monopotassium or sodium pyrophosphates, di-alkali metal pyrophosphates, tetra-alkali metal pyrophosphates, and mixtures thereof. In one embodiment, the pyrophosphate is selected from the group consisting of trisodium pyrophosphate, disodium dihydrogen pyrophosphate (Na2H2P2O7), dipotassium pyrophosphate, tetrasodium pyrophosphate (Na4P2O7), tetrapotassium pyrophosphate (K4P2O7), and mixtures thereof. Pyrophosphates are described in U.S. Patent Nos. 4,515,772 (Parran et al.) Issued May 7, 1985 and 4,885,155 (Parran et al.) Issued December 5, 1989, together with the publications cited therein. The pyrophosphates are described in more detail in Kirk & Othmer, Encyclopedia of Chemical Technology, Third Edition, Vol. 17, Wiley-Interscience Publishers (1982), pp. 685-707.

In one embodiment, the composition comprises tetra-sodium pyrophosphate. The tetrasodium pyrophosphate may be in the form of an anhydrous salt or a 10-aqueous hydrate, or be in any other form stable in the composition of the invention. The solid salt may be crystalline and / or amorphous, with the particle size preferably being small enough so that the appearance is aesthetically acceptable and the salt readily soluble upon use.

The level of pyrophosphate in the composition according to the invention is 4.5-40% by weight of the composition.

Other anti-tartar remedies

The following agents may be used as other anti-tartar agents. The olefin polysulfonates useful in the invention are those compounds wherein the olefinic group contains 2 or more carbon atoms, and the salts thereof. Olefin polyphosphonates are compounds in which the olefinic group contains 2 or more carbon atoms. Vinyl polyphosphonates include polyvinylphosphonic acid. Diphosphonates and their salts include azocycloalkane-2,2-diphosphonic acids and their salts, azocycloalkane-2,2-diphosphonic acid ions and their salts (such where the alkane group contains five, six or seven carbon atoms and the nitrogen atom is unsubstituted) or substituted with lower alkyl, e.g. methyl), azacyclohexane-2,2-diphosphonic acid, azacyclopentane-2,2-diphosphonic acid, N-methylazacyclopentane-2,3-diphosphonic acid, EHDP (ethanehydroxy-1,1-diphosphonic acid), AHP (2-azacycloheptane acid) , 2-diphosphonic; aka (1-azocycloheptylidene-2,2-diphosphonic acid), ethane-1-amino-1,1-diphosphonate, dichloromethane diphosphonate etc. The phosphonoalkane carboxylic acids and their alkali metal salts include PPTA (phosphonopropane tricarboxylic acid), PBTA (phosphonobutane-1,2,4-tricarboxylic acid), each in the form of an alkali metal acid or salt. Olefin polyphosphates include compounds in which the olefinic group contains 2 or more carbon atoms. Polypeptides include poly aspartic acid and glutamic acid.

Azacycloalkane-2,2-diphosphonic acids are disclosed in U.S. Patent Nos. 3,941,772 (Ploger et al.) Issued March 2, 1976 assigned to Henkel and 3,988,443 (Ploger et al.) Issued October 26, 1976.

Non-aqueous carrier of the denture adhesive component

The non-aqueous carrier of the denture adhesive component is selected from the group consisting of a non-aqueous carrier substance and a non-adhesive self-supporting layer. The level of non-aqueous carrier content can be about 20-60% by weight of the composition.

Non-aqueous carrier substance

The non-aqueous carrier substance is in any chemical and physical form that does not contain water. As stated above, the non-aqueous carrier substance is selected from the group consisting of liquid paraffin, petroleum jelly, mineral oil, glycerin, natural and synthetic oils, fats, silicones and silicone derivatives, polyvinyl acetate, natural and synthetic waxes such as animal waxes, e.g.

Bees, lanolin and shellac, hydrocarbons, hydrocarbon derivatives, vegetable oil waxes such as carnauba wax, candelilla and miter wax, vegetable oils such as octanoic / decanoic acid triglycerides, and in another embodiment is selected from the group consisting of liquid paraffin , petroleum jelly, mineral oil, vegetable oils such as corn, soybean, cottonseed, castor, palm and coconut oil, and animal oils such as fish oil, and oleic acid and mixtures thereof and in yet another embodiment it is mineral oil.

Octanoic / decanoic acid triglycerides are triglycerides of medium-chain acids in which the -C == OR group contains 8-10 carbon atoms, obtained by adding glycerin to a mixture of decanoic and octanoic acids:

octanoic acid: CH3 (CH2) 6CO2H decanoic acid: CH3 (CH2) 8CO2H

Thus, according to the invention, vegetable oils containing medium chain saturated fatty acids such as octanoic acid, decanoic acid and mixtures thereof can be used. Such vegetable oils and other non-aqueous substances forming the adhesive medium of a denture composition are further described in U.S. Patent No. 5,561,177 (Khaledi et al.) Issued October 1, 1996.

Self-supporting non-stick layer

The non-aqueous carrier may be at least one non-stick self-supporting layer. The non-stick self-supporting layer is characterized by the ability to maintain strength and integrity of the adhesive composition in the presence of water and / or saliva. As stated above, the non-adhesive self-supporting layer may include materials such as polyester, polypropylene, nylon, rayon, cellulose acetate, non-stick cellulose derivatives, fabric, fleece, paper, plastic, leather, microcrystalline wax, synthetic fibers, natural fibers and their mixtures. Non-stick cellulose derivatives, polyester, polypropylene, nylon, rayon, fabric, paper, microcrystalline wax and mixtures thereof are preferred. Polyester, polypropylene, rayon, nylon, fabric and paper are more preferred.

The non-adhesive self-supporting layer may take any physical form suitable for providing strength and / or integrity to the adhesive composition of the invention. Such physical forms are nonwovens, woven fabrics, continuous materials, staple materials, foams, and combinations of these materials. In addition, the non-stick self-supporting layer may be formed by any commonly known process. Such processes are non-bonding, spray-bonding, spinning-bonding, needle-stitching, grempling, hydro-entangling thermal bonding, melt blowing, hole pattern printing, needling, wet piling, dry layering, and a combination of these processes.

The inventive adhesive denture compositions comprising a non-adhesive self-supporting layer may also include a coating that adheres to the dry denture and, if present, disposed on one side of the adhesive denture composition. Compositions suitable for using this type of adhesive layer include silicones, rubbers, petroleum jelly, natural polymers, synthetic polymers, and mixtures thereof. The adhesive layer may be present in the composition from about 0-70%, and in another embodiment from about 0.5-20%, by weight of the composition.

Various media

Other suitable ingredients are coloring agents, preservatives (such as methylparaben and propylparaben), thickening agents such as silicon dioxide and polyethylene glycol. Coloring agents, preservatives, and thickening agents may be present in an amount of about 0-20% by weight of the composition.

Softeners

The compositions according to the invention may additionally contain one or more toxicologically acceptable plasticizers. The term "toxicologically acceptable" as used herein defines materials which, due to their toxic properties, are suitable for administration to humans and / or animals. Plasticizers such as dimethyl phthalate, diethyl phthalate, dioctyl phthalate, glycerin, diethylene glycol, triethylene glycol, Igepal®, Gafac®, sorbitol, tricresyl phosphate, dimethyl sebacate, ethyl glycolate, ethyl phthalate, ethyl phthalate, may be used in the composition according to the invention. o- and p-toluene ethylsulfonamide and mixtures thereof. The plasticizer content may be from about 0-70%, in another embodiment from about 1-30%, by weight of the composition.

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Flavoring agents, fragrances, sensory agents

The compositions of the invention may also contain one or more ingredients imparting the desired flavor, aroma and / or sensory properties to the composition (heating or cooling agents). Suitable ingredients are natural and artificial sweeteners, menthol, menthyl lactate, wintergreen oil, peppermint oil, spearmint oil, cis-3-hexen-1-ol, clove oil, anethole, methyl salicylate, eucalyptol, cassia oil, acetate 1-8-menthyl, sage, eugenol, parsley oil, oxanone, α-irisone, marjoram, lemon oil, orange oil, propenylgwaetol, cinnamon oil, vanilla, thymol, linalool, cinnamaldehyde glyceryl acetal known as CGA, and mixtures thereof, as well as cooling agents. A coolant can be a wide variety of compounds. These include carboxamides, menthol, ketals, diols and mixtures thereof. Preferred cooling agents in the composition of the invention are paramentane carboxamide agents such as N-ethyl-p-menthane-3-carboxamide, commercially known as "WS-3, N, 2,3-trimethyl-2-isopropylbutanamide, known as" WS-3, N, 2,3-trimethyl-2-isopropylbutanamide " -23, and mixtures thereof. Additional preferred cooling agents are selected from the group consisting of menthol, 3-1-menthoxypropane-1,2-diol, known as TK-10, manufactured by Takasago, menthone glyceryl acetal, known as MGA, manufactured by Haarmann and Reimer, and menthyl lactate, known as Frescolat®, manufactured by Haarmann and Reimer. The term menthol and menthyl as used herein includes the right- and left-handed isomers of these compounds and their racemic mixtures. TK-10 is described in U.S. Patent No. 4,459,425 (Amano et al.) Issued 7/10/84, and WS-3 and other agents are described in U.S. Patent No. 4,136,163 (Watson et al.) Issued January 23, 1979. The content of these agents may be about 0-50% by weight of the composition.

Other optional ingredients

Denture adhesive compositions may also be used as denture adhesive and / or biological adhesive and may contain one or more therapeutically active agents suitable for topical administration. The content of therapeutically active agents may be from about 0-70% by weight of the composition, and in one embodiment from about 1-20% by weight of the composition. Therapeutically active agents include antimicrobials such as iodine, tricolsan, peroxides, sulfonamides, bisbiguanides, or phenolic compounds; antibiotics such as tetracycline, neomycin, kanamycin, metronidazole, cetylpyridium chloride or clindamycin; anti-inflammatory agents such as aspirin, acetaminophen, naproxen and its salts, ibuprofen, ketorolac, flurbiprofen, indomethacin, eugenol or hydrocortisone; dentin desensitizing agents such as potassium nitrate, strontium chloride or sodium fluoride; fluorides such as sodium fluoride, tin fluoride, MFP; anesthetics such as lidocaine or anesthesin; antifungal agents such as are used in the treatment of candida albicans infection; perfumes such as camphor, eucalyptus oil, and aldehyde derivatives such as benzaldehyde; insulin; steroids; herbal and herbal remedies; baking soda and anti-cancer agents. It should be understood that in some embodiments of the therapy, the combination of these agents in the same delivery system may be beneficial to achieve optimal results. For example, an antimicrobial and an anti-inflammatory agent can be combined in a single delivery system to achieve enhanced efficacy.

The method of making the composition

The method of making the adhesive denture compositions of the present invention (creams, powders, wafers, non-aqueous liquids, aerosols, pastes) includes the known methods disclosed. Known preparation processes are described in US Patent Nos. 5,525,652 (Clarke et al.) Issued June 11, 1996; 3,003,988, Germann et al., Issued Oct. 10, 1961; 5,073,604 (Holeva et al.) Filed December 17, 1991 and 5,872,161 (Liang et al.) Filed February 16, 1999.

The method of producing the inventive adhesive denture compositions comprising a non-adhesive self-supporting layer comprises applying a weighed amount of an adhesive component to the non-adhesive self-supporting layer. This method is disclosed in US Patent Nos. 5,877,233 (Liang et al.) Issued March 2, 1999; 5,872,160 (Liang et al.) On 2/16/99 and 5,880,172 (Rajaiah et al.) On October 2, 1996.

Application method

The adhesive composition may take the form of a powder, cream, paste, non-aqueous liquid, aerosol, and / or wafer. The cream, paste and other compositions according to the invention are generally applied to the denture which is then deposited in the oral cavity in known manner.

The following examples further describe and demonstrate various embodiments of the invention falling within its scope.

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Example I.

Denture stabilizing cream compositions were prepared by mixing the following ingredients:

<td></td><td>AND</td><td>B</td><td>C.</td><td>D</td><td>E.</td>

<td></td><td>g</td><td>g</td><td>g</td><td>g</td><td>g</td>

<td>Paraffin oil</td><td> 23,93</td><td> 23,93</td><td> 23,93</td><td> 23,93</td><td> 23,93</td>

<td>White petroleum jelly</td><td> 19,8</td><td> 8,87</td><td> 14,37</td><td> 16,87</td><td> 16,87</td>

<td>Sodium carboxymethylcellulose</td><td> 20,00</td><td> 20,00</td><td> 20,00</td><td> 20,00</td><td> 20,00</td>

<td>Colloidal silicon dioxide</td><td> 1,14</td><td> 1,14</td><td> 1,14</td><td> 1,14</td><td> 1,14</td>

<td>Coloring agent (Opatint Red Dye)</td><td> 0,06</td><td> 0,06</td><td> 0,06</td><td> 0,06</td><td> 0,06</td>

<td>Any salt form, acid or anhydride form AVE / MA and / or AVE / MA / IB</td><td> 33,00</td><td> 33,00</td><td> 33,00</td><td> 33,00</td><td> 33,00</td>

<td>Tetrasodium Pyrophosphate (TSPP)</td><td> 2,05</td><td> -</td><td> 2,50</td><td></td><td></td>

<td>EHDP (ethanehydroxy-1,1-diphosphonic acid)</td><td></td><td></td><td></td><td> 5,00</td><td></td>

<td>AHP (azacycloheptane-2,2-diphosphonic acid)</td><td></td><td></td><td></td><td></td><td> 5,00</td>

<td>Polyphosphate (Glass-H¹)</td><td> -</td><td> 13,00</td><td> 5,00</td><td></td><td></td>

¹Polyphosphate produced by FMC Corporation, n = 21 (average).

The red dye, petroleum jelly and mineral oil were weighed, the mixture was heated and stirred in a glass vessel at 50-60 ° C until visual homogeneity was achieved. The powders (colloidal silicon dioxide, CMC, AVE / MA, AVE / MA / IB and TSPP or AHP or EHDO or Glass-H) were then weighed and mixed by shaking in the container. The powders were then mixed with the liquid with a lab spatula until a visually homogeneous pink cream was achieved. The above compositions can be modified by increasing or decreasing the TSPP content in the range 0-15 g, the Glass-H content in the range 0-15 g, AVE / MA or AVE / MA / IB in the range 0-15 g, Vaseline in the range 0-15 g g and / or CMC in the range 0-15 g. The above compositions may also be modified with a suitable other anti-tartar agent. The user puts 0.1 - 5 g of cream on the denture. The user then places the prosthesis in the mouth and presses it into place.

Example II

Adhesive denture compositions in powder form were prepared by mixing the following ingredients:

<td></td><td>AND</td><td>B</td><td>C.</td><td>D</td><td>E.</td>

<td>Sodium carboxymethylcellulose</td><td> 20,00</td><td> 20,00</td><td> 20,00</td><td> 20,00</td><td> 20,00</td>

<td>Colloidal silicon dioxide</td><td> 1,14</td><td> 1,14</td><td> 1,14</td><td> 1,14</td><td> 1,14</td>

<td>Any salt form, acid or anhydride form AVE / MA and / or AVE / MA / IB</td><td> 33,00</td><td> 33,00</td><td> 33,00</td><td> 33,00</td><td> 33,00</td>

<td>Tetrasodium Pyrophosphate (TSPP)</td><td> 2,05</td><td> -</td><td> 2,50</td><td></td><td></td>

<td>EHDP (ethanehydroxy-1,1-diphosphonic acid)</td><td></td><td></td><td></td><td> 5,00</td><td></td>

<td>AHP (azacycloheptane-2,2-diphosphonic acid</td><td></td><td></td><td></td><td></td><td> 5,00</td>

<td>Polyphosphate (Glass-H¹)</td><td> -</td><td> 13,00</td><td> 5,00</td><td></td><td></td>

All ingredients were mixed together. The above compositions can be modified by increasing or decreasing the TSPP content in the range 0-15 g, the Glass-H content in the range

PL 200 510 B1

- 15 g, AHP in the range 0 - 15 g, EHDP in the range 0 - 15 g, AVE / MA or AVE / MA / IB in the range 0 - 15 g, petroleum jelly in the range 0 - 15 g and / or CMC in the range 0 - G. The above compositions may also be modified with suitable other anti-tartar agents. The user applies 0.1-5 g of the composition to the denture, wets it, places it in the mouth and presses it into place.

Example III

The adhesive wafer compositions were prepared by wetting a 147.32 x 50.8 cm polyester non-woven fabric (non-stick backing layer) with water. The wetted sheet was evenly coated with the compositions of Example 2 in an amount 1-3 times the weight of the sheet. The layer was then re-wetted with water and dried. The composition was mechanically softened with a ring roller and smoothed on a hydraulic press. The compositions were then punched into desired shapes and the thus formed wafers of the composition were wetted and applied to dentures. The denture is placed in the mouth and pressed into place.