# US 8,236,337 B2 · Anti-microbial orthodontic compositions and appliances and methods of production and use thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,236,337 B2 - Document ID: US8236337B2 - Status: Granted - Kind: B2 - Application number: 12/460,046 - Filed: 2009-07-13 - Published: 2010-02-04 - Granted: 2012-08-07 - Earliest claimed: 2005-05-24 - Assignees: Selenium, Ltd. - Inventors: Ted Reid; Julian Spallholz; Thirumal N. Devanathan; Thomas Mosley - Web page: https://patentgrep.com/patent/US8236337B2 ## CPC - A01N 55/00: Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur (containing organo-phosphorus compounds A01N57/00) - A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration} - A61K 31/095: Sulfur, selenium, or tellurium compounds, e.g. thiols - A61K 31/26: Cyanate or isocyanate esters; Thiocyanate or isothiocyanate esters - A61K 31/655: Azo (—N=N—), diazo (=N2), azoxy (>N—O—N< or N(=O)—N<), azido (—N3) or diazoamino (—N=N—N<) compounds - A61K 33/04: Sulfur, selenium or tellurium; Compounds thereof - A61K 47/02: Inorganic compounds - A61K 47/32: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers {, poly(meth)acrylates, or polyvinyl pyrrolidone} - C07C 391/00: Compounds containing selenium - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract The presently disclosed and claimed invention is directed to anti-microbial orthodontic apparatus and anti-microbial orthodontic compositions comprising an effective amount of a selenium compound, kits containing same, and methods of producing and using said anti-microbial orthodontic apparatus and anti-microbial orthodontic compositions. ## Claims ### Claim 1 An anti-microbial orthodontic apparatus, comprising: an orthodontic device; an anti-microbial coating applied to the orthodontic device, wherein the anti-microbial coating comprises an effective amount of a selenium compound, wherein the selenium compound is selected from the group consisting of 3-[3-(2-{1-Methyl-2-[2-(2-methyl-acryloyloxy)-ethoxycarbonyl]-ethoxycarbonyl}-ethyldiselenyl)propionyl oxy]-butyric acid 2-(2-methyl-acryloyloxy)-ethyl ester (diSeAAEMA) and Di(cyclohexylmethyl-selenide), and wherein the selenium compound allows for formation of the selenium anion Se— and free radical species and provides permanent attachment of the selenium anion Se— to a surface of the orthodontic device. ### Claim 2 (depends on 1) The anti-microbial orthodontic apparatus of claim 1, wherein the selenium compound is non-covalently associated with the orthodontic device. ### Claim 3 (depends on 1) The anti-microbial orthodontic apparatus of claim 1, wherein the selenium is present in the anti-microbial coating at a concentration in a range of from about 1% to about 10%. ### Claim 4 (depends on 1) The anti-microbial orthodontic apparatus of claim 1, wherein the effective amount of the selenium compound is in a range of from about 0.01 μg to about 100 μg of elemental selenium per square centimeter of surface area. ### Claim 5 (depends on 1) The anti-microbial orthodontic apparatus of claim 1, wherein the orthodontic device is at least one of a bracket, an arch wire, a closing chain, a ligature tie, a retainer, a brace, a molar band, and a buccal tube. ### Claim 6 An anti-microbial orthodontic composition, comprising: an orthodontic composition; an anti-microbial composition disposed in the orthodontic composition, the anti-microbial composition comprising an effective amount of a selenium compound, wherein the selenium compound is selected from the group consisting of 3-[3-(2-{1-Methyl-2-[2-(2-methyl-acryloyloxy)-ethoxycarbonyl]-ethoxycarbonyl}-ethyldiselenyl) propionyl oxy]-butyric acid 2-(2-methyl-acryloyloxy)-ethyl ester (diSeAAEMA) and Di(cyclohexylmethyl-selenide), and wherein the selenium compound allows for formation of the selenium anion Se— and free radical species and provides permanent attachment of the selenium anion Se— to a surface to which the orthodontic composition is applied. ### Claim 7 (depends on 6) The anti-microbial orthodontic composition of claim 6, wherein the selenium is present in the anti-microbial composition at a concentration in a range of from about 1% to about 10%. ### Claim 8 (depends on 6) The anti-microbial orthodontic composition of claim 6, wherein the orthodontic composition is at least one of an adhesive, a sealant, a cement, and an orthodontic device coating. ### Claim 9 (depends on 8) The anti-microbial orthodontic composition of claim 8, wherein the adhesive is at least one of a self-cure adhesive and a light cure adhesive. ### Claim 10 (depends on 8) The anti-microbial orthodontic composition of claim 8, wherein the sealant is a light cure sealant. ### Claim 11 (depends on 8) The anti-microbial orthodontic composition of claim 8, wherein the cement is a light cure cement. ### Claim 12 (depends on 6) The anti-microbial orthodontic composition of claim 6, further comprising at least one methacrylate compound. ### Claim 13 (depends on 12) The anti-microbial orthodontic composition of claim 12, wherein the at least one methacrylate compound is 2-(Acetoacetoxy)ethylmethacrylate (AAEMA). ### Claim 14 A kit, comprising: an anti-microbial orthodontic composition comprising: at least one of an adhesive, a sealant and a cement; an anti-microbial composition disposed in the at least one of an adhesive, a sealant and a cement, the anti-microbial composition comprising an effective amount of a selenium compound, wherein the selenium compound is selected from the group consisting of 3-[3-(2-{1-Methyl-2-[2-(2-methyl-acryloyloxy)-ethoxycarbonyl]-ethoxycarbonyl}-ethyldiselenyl)propionyl oxy]-butyric acid 2-(2-methyl-acryloyloxy)-ethyl ester (diSeAAEMA) and Di(cyclohexylmethyl-selenide), and wherein the selenium compound allows for formation of the selenium anion Se— and free radical species and provides permanent attachment of the selenium anion Se— to a surface to which the orthodontic composition is applied; and an activator. ### Claim 15 (depends on 14) The kit of claim 14, further comprising an etchant. ### Claim 16 (depends on 14) The kit of claim 14, wherein the selenium is present in the anti-microbial composition at a concentration in a range of from about 1% to about 10%. ### Claim 17 A kit, comprising: an orthodontic device; and an anti-microbial orthodontic composition comprising: at least one of an adhesive, a sealant and a cement; an anti-microbial composition disposed in the at least one of an adhesive, a sealant and a cement, the anti-microbial composition comprising an effective amount of a selenium compound, wherein the selenium compound is selected from the group consisting of 3-[3-(2-{1-Methyl-2-[2-(2-methyl -acryloyloxy)-ethoxycarbonyl]-ethoxycarbonyl}-ethyldiselenyl)propionyl oxy]-butyric acid 2-(2-methyl-acryloyloxy)-ethyl ester (diSeAAEMA) and Di(cyclohexylmethyl-selenide), and wherein the selenium compound allows for formation of the selenium anion Se— and free radical species and provides permanent attachment of the selenium anion Se— to a surface of the orthodontic device. ### Claim 18 (depends on 17) The kit of claim 17, wherein the selenium compound is non-covalently associated with the orthodontic device when the anti-microbial orthodontic composition is applied to the orthodontic device. ### Claim 19 (depends on 17) The kit of claim 17, wherein the orthodontic device is at least one of a bracket, an arch wire, a closing chain, a ligature tie, a retainer, a brace, a molar band, and a buccal tube. ### Claim 20 (depends on 17) The kit of claim 17, wherein the orthodontic device is a molar band and the anti-microbial orthodontic composition is a band cement. ### Claim 21 (depends on 17) The kit of claim 17, wherein the effective amount of the selenium compound present in the anti-microbial orthodontic composition is in a range of from about 0.01 μg to about 100 μg of elemental selenium per square centimeter of surface area. ### Claim 22 (depends on 17) The kit of claim 17, further comprising an anti-microbial coating applied to the orthodontic device, wherein the anti-microbial coating comprises an effective amount of a selenium compound, wherein the selenium compound is selected from the group consisting of 3-[3-(2-{1-Methyl-2-[2-(2-methyl-acryloyloxy)-ethoxycarbonyl]-ethoxycarbonyl} ethyldiselenyl) propionyl oxy]-butyric acid 2-(2-methyl-acryloyloxy)-ethyl ester (diSeAAEMA) and Di(cyclohexylmethyl-selenide), and wherein the selenium compound is non-covalently associated with the orthodontic device. ### Claim 23 (depends on 22) The kit of claim 22, wherein the selenium is present in the anti-microbial coating at a concentration in a range of from about 1% to about 10%. ### Claim 24 (depends on 22) The kit of claim 22, wherein the effective amount of the selenium compound present in the anti-microbial coating is in a range of from about 0.01 μg to about 100 μg of elemental selenium per square centimeter of surface area. ### Claim 25 A method of producing an anti-microbial orthodontic apparatus, comprising the step of: applying an anti-microbial coating to an orthodontic device, wherein the anti-microbial coating comprises an effective amount of a selenium compound, wherein the selenium compound is selected from the group consisting of 3-[3-(2-{1-Methyl-2-[2-(2-methyl-acryloyloxy)-ethoxycarbonyl]-ethoxycarbonyl}-ethyldiselenyl) propionyloxy]-butyric acid 2-(2-methyl-acryloyloxy)-ethyl ester (diSeAAEMA) and Di(cyclohexylmethyl-selenide), and wherein the selenium compound allows for formation of the selenium anion Se— and free radical species and provides permanent attachment of the selenium anion Se— to a surface of the orthodontic device. ### Claim 26 (depends on 25) The method of claim 25 wherein, in the step of applying the anti-microbial coating to the orthodontic device, the selenium compound is non-covalently associated with the orthodontic device. ### Claim 27 (depends on 25) The method of claim 25 wherein, in the step of providing the anti-microbial coating, the selenium is present in the anti-microbial coating at a concentration in a range of from about 1% to about 10%. ### Claim 28 (depends on 25) The method of claim 25 wherein, in the step of applying the anti-microbial coating to the orthodontic device, the effective amount of the selenium compound is in a range of from about 0.01 μg to about 100 μg of elemental selenium per square centimeter of surface area. ### Claim 29 (depends on 25) The method of claim 25 wherein, in the step of providing an orthodontic device, the orthodontic device is at least one of a bracket, an arch wire, a closing chain, a ligature tie, a retainer, a brace, a molar band, and a buccal tube. ### Claim 30 A method of producing an anti-microbial orthodontic composition, comprising the step of: disposing an anti-microbial composition into an orthodontic composition to provide an anti-microbial orthodontic composition, the anti-microbial composition comprising an effective amount of a selenium compound, wherein the selenium compound is selected from the group consisting of 3-[3-(2-{1-Methyl-2-[2-(2-methyl-acryloyloxy)-ethoxycarbonyl]-ethoxycarbonyl}-ethyldiselenyl)propionyl oxy]-butyric acid 2-(2-methyl-acryloyloxy)-ethyl ester (diSeAAEMA) and Di(cyclohexylmethyl-selenide), and wherein the selenium compound allows for formation of the selenium anion Se— and free radical species and provides permanent attachment of the selenium anion Se— to a surface to which the orthodontic composition is applied. ### Claim 31 (depends on 30) The method of claim 30 wherein, in the step of disposing the anti-microbial composition into the orthodontic composition, the selenium is present in the anti-microbial orthodontic composition at a concentration in a range of from about 1% to about 10%. ### Claim 32 (depends on 30) The method of claim 30 wherein, in the step of providing an orthodontic composition, the orthodontic composition is at least one of an adhesive, a sealant, a cement, and an orthodontic device coating. ### Claim 33 (depends on 32) The method of claim 32, wherein the adhesive is at least one of a self-cure adhesive and a light cure adhesive. ### Claim 34 (depends on 32) The method of claim 32, wherein the sealant is a light cure sealant. ### Claim 35 (depends on 32) The method of claim 32, wherein the cement is a light cure cement. ### Claim 36 (depends on 30) The method of claim 30, wherein the anti-microbial composition further comprises at least one methacrylate compound. ### Claim 37 (depends on 36) The method of claim 36, wherein the at least one methacrylate compound is AAEMA. ### Claim 38 A method of binding an orthodontic device to a tooth, comprising the step of: binding an orthodontic device to a tooth with an effective amount of an anti-microbial orthodontic composition, whereby the anti-microbial orthodontic composition prevents the growth of microbes on at least one of the orthodontic device and the tooth, and wherein the ant-microbial orthodontic composition comprises at least one of an adhesive, a sealant and a cement having an anti-microbial composition disposed therein, the anti-microbial composition disposed in the at least one of an adhesive, a sealant and a cement comprising an effective amount of a selenium compound, wherein the selenium compound is selected from the group consisting of 3-[3-(2-{1-Methyl-2-[2-(2-methyl-acryloyloxy)-ethoxycarbonyl]-ethoxycarbonyl}-ethyldiselenyl)propionyl oxy]-butyric acid 2-(2-methyl-acryloyloxy)-ethyl ester (diSeAAEMA) and Di(cyclohexylmethyl-selenide), and wherein the selenium compound allows for formation of the selenium anion Se— and free radical species and provides permanent attachment of the selenium anion Se— to a surface of at least one of the orthodontic device and the tooth. ### Claim 39 (depends on 38) The method of claim 38 wherein, in the step of binding the orthodontic device to the tooth, the selenium compound is non-covalently associated with the at least one of the orthodontic device and the tooth. ### Claim 40 (depends on 38) The method of claim 38 wherein, in the step of providing an orthodontic device, the orthodontic device is at least one of a bracket, an arch wire, a closing chain, a ligature tie, a retainer, a brace, a molar band, and a buccal tube. ### Claim 41 (depends on 40) The method of claim 40, wherein the orthodontic device is a molar band and the anti-microbial orthodontic composition is a band cement. ### Claim 42 (depends on 38) The method of claim 38, wherein the selenium is present in the anti-microbial orthodontic composition at a concentration in a range of from about 1% to about 10%. ### Claim 43 (depends on 38) The method of claim 38, wherein the effective amount of the selenium compound present in the anti-microbial orthodontic composition is in a range of from about 0.01 μg to about 100 μg of elemental selenium per square centimeter of surface area. ### Claim 44 (depends on 38) The method of claim 38 wherein, in the step of providing an orthodontic device, the orthodontic device further comprises an anti-microbial coating applied thereto, wherein the anti-microbial coating comprises an effective amount of a selenium compound, wherein the selenium compound is selected from the group consisting of 3-[3-(2-{1-Methyl-2-[2-(2-methyl-acryloyloxy)-ethoxycarbonyl]-ethoxycarbonyl}-ethyldiselenyl) propionyl oxy]-butyric acid 2-(2-methyl-acryloyloxy)-ethyl ester (diSeAAEMA) and Di(cyclohexylmethyl-selenide). ### Claim 45 (depends on 44) The method of claim 44, wherein the selenium is present in the anti-microbial coating at a concentration in a range of from about 1% to about 10%. ### Claim 46 (depends on 44) The method of claim 44, wherein the effective amount of the selenium compound present in the anti-microbial coating is in a range of from about 0.01 μg to about 100 μg of elemental selenium per square centimeter of surface area. ### Claim 47 (depends on 38) The method of claim 38, wherein the step of binding the orthodontic device to the tooth further includes the step of activating the adhesive, the sealant or cement the anti-microbial orthodontic composition. ### Claim 48 (depends on 38) The method of claim 38, wherein the step of binding the orthodontic device to the tooth comprises the steps of: preparing a surface of the tooth with an etchant; applying an activator to a surface of at least one of the tooth and the orthodontic device; applying the anti-microbial orthodontic composition to a surface of at least one of the tooth and the orthodontic device; and applying the orthodontic device to the tooth. ### Claim 49 (depends on 38) The method of claim 38, further comprising the step of applying an effective amount of an anti-microbial dental composition to the tooth, wherein the anti-microbial dental composition comprises a sealant having an anti-microbial composition disposed therein, the anti-microbial composition comprising an effective amount of a selenium compound, wherein the selenium compound is selected from the group consisting of 3-[3-(2-{1-Methyl-2-[2-(2-methyl-acryloyloxy)-ethoxycarbonyl]-ethoxycarbonyl}-ethyldiselenyl)propionyl oxy]-butyric acid 2-(2-methyl-acryloyloxy)-ethyl ester (diSeAAEMA) and Di(cyclohexylmethyl-selenide), wherein the selenium compound allows for formation of the selenium anion Se— and free radical species and provides permanent attachment of the selenium anion Se— to a surface of the tooth. ### Claim 50 A method of binding an anti-microbial device to a tooth, comprising the step of: binding an anti-microbial orthodontic apparatus to a tooth, the anti-microbial orthodontic apparatus comprising an orthodontic device having an anti-microbial coating applied thereto, whereby the anti-microbial coating prevents the growth of microbes on the orthodontic device, and wherein the anti-microbial coating comprises an effective amount of a selenium compound, wherein the selenium compound is selected from the group consisting of 3-[3-(2-{1-Methyl-2-[2-(2-methyl-acryloyloxy)-ethoxycarbonyl]-ethoxycarbonyl}-ethyldiselenyl)propionyl oxy]-butyric acid 2-(2-methyl-acryloyloxy)-ethyl ester (diSeAAEMA) and Di(cyclohexylmethyl-selenide), wherein the selenium compound allows for formation of the selenium anion Se— and free radical species and provides permanent attachment of the selenium anion Se— to a surface of the orthodontic device. ### Claim 51 (depends on 50) The method of claim 50 wherein, in the step of binding the anti-microbial orthodontic apparatus to the tooth, the selenium compound is non-covalently associated with the orthodontic device. ### Claim 52 (depends on 50) The method of claim 50 wherein, in the step of providing an orthodontic device, the orthodontic device is at least one of a bracket, an arch wire, a closing chain, a ligature tie, a retainer, a brace, a molar band, and a buccal tube. ### Claim 53 (depends on 52) The method of claim 52, wherein the orthodontic device is a molar band and the anti-microbial orthodontic composition is a band cement. ### Claim 54 (depends on 50) The method of claim 50 wherein, in the step of providing the anti-microbial orthodontic apparatus, the selenium is present in the anti-microbial coating at a concentration in a range of from about 1% to about 10%. ### Claim 55 (depends on 50) The method of claim 50 wherein, in the step of providing an anti-microbial orthodontic apparatus, the effective amount of the selenium compound is in a range of from about 0.01 μg to about 100 μg of elemental selenium per square centimeter of surface area. ### Claim 56 (depends on 50) The method of claim 50, further comprising the step of applying an effective amount of an anti-microbial dental composition to the tooth, wherein the anti-microbial dental composition comprises a sealant having an anti-microbial composition disposed therein, the anti-microbial composition comprising an effective amount of a selenium compound, wherein the selenium compound is selected from the group consisting of 3-[3-(2-{1-Methyl-2-[2-(2-methyl-acryloyloxy)-ethoxycarbonyl]-ethoxycarbonyl}-ethyldiselenyl)propionyl oxy]-butyric acid 2-(2-methyl-acryloyloxy)-ethyl ester (diSeAAEMA) and Di(cyclohexylmethyl-selenide), wherein the selenium compound allows for formation of the selenium anion Se— and free radical species and provides permanent attachment of the selenium anion Se— to a surface of the tooth. ### Claim 57 A method of applying an antimicrobial coating to a tooth, comprising the step of: disposing an effective amount of the anti-microbial dental composition on at least a portion of the tooth, thereby preventing the growth of microbes on the tooth, wherein the anti-microbial dental composition comprises a sealant having an anti-microbial composition disposed therein, the anti-microbial composition comprising an effective amount of a selenium compound, wherein the selenium compound is selected from the group consisting of 3-[3-(2-{1-Methyl-2-[2-(2-methyl -acryloyloxy)-ethoxycarbonyl]-ethoxycarbonyl}-ethyldiselenyl)propionyl oxy]-butyric acid 2-(2-methyl-acryloyloxy)-ethyl ester (diSeAAEMA) and Di(cyclohexylmethyl-selenide), wherein the selenium compound allows for formation of the selenium anion Se— and free radical species and provides permanent attachment of the selenium anion Se— to a surface of the tooth. ### Claim 58 (depends on 57) The method of claim 57, wherein the selenium is present in the anti-microbial dental composition at a concentration in a range of from about 1% to about 10%. ### Claim 59 (depends on 57) The method of claim 57, wherein the effective amount of the selenium compound present in the anti-microbial orthodontic composition is in a range of from about 0.01 μg to about 100 μg of elemental selenium per square centimeter of surface area. ### Claim 60 (depends on 57) The method of claim 57, wherein the method further comprises the step of activating the anti-microbial dental composition.