Curable compositions with antimicrobial properties

Abstract

Novel curable compositions are disclosed which include a water-insoluble antimicrobial agent. The curable compositions are useful in inhibiting the growth of bacteria on the surface of the curable composition, within the curable compositions and in a volume adjacent to the curable composition.

1 . A material for placement within an oral cavity, the material comprising: 
 a curable composition capable of being rendered from a first malleable phase to a second phase with substantially resists a change in size and shape;    a water-insoluble antimicrobial agent releasable from the material in a manner to create a zone of inhibition within which growth of bacteria is inhibited.    
     
     
         2 . A material as set forth in    claim 1   , wherein the curable composition includes a free radical polymerization initiator which, when activated, renders the composition into the second phase.  
     
     
         3 . A material as set forth in    claim 1   , wherein the water-insoluble antimicrobial agent is provided at a concentration sufficient to substantially prevent microbial growth on the material when the material comes into contact with the oral cavity.  
     
     
         4 . A material as set forth in    claim 3   , wherein the water-insoluble antimicrobial agent is selected from the group consisting of halogenated diphenyl ethers, halogenated salicylanilides, benzoic esters, halogenated carbanalides, and phenolic compounds.  
     
     
         5 . A material as set forth in    claim 1   , wherein the water-insoluble antimicrobial agent is provided at a concentration of between about 0.10% by weight and less than 4% by weight of the composition.  
     
     
         6 . A method for forming an antimicrobial material for placement within an oral cavity, the method comprising: 
 providing a curable composition capable of being rendered from a first malleable phase to a second phase which substantially resist change in size and shape;    forming a mixture between the composition in its first phase and an antimicrobial agent;    curing the mixture so as to render the composition into its second phase, and    allowing the curable composition to release the antimicrobial agent to produce a zone of inhibition within which the growth of bacteria is inhibited.    
     
     
         7 . A material as set forth in    claim 6   , wherein the water-insoluble antimicrobial agent is a member selected from the group consisting of halogenated diphenyl ethers, halogenated salicylanilides, benzoic esters, halogenated carbanalides, and phenolic compounds.  
     
     
         8 . A material as set forth in    claim 6   , wherein the water-insoluble antimicrobial agent is provided at a concentration of between about 0.10% by weight and less than 4% by weight of the composition.  
     
     
         9 . A curable composition for use in forming an artificial prosthesis comprising: 
 a mixture of a polymerization system and a water-insoluble antimicrobial agent which remains inert to the polymerization system,    the mixture capable of being cured to produce an artificial prosthesis characterized as having a zone of inhibition of growth of bacteria surrounding the artificial prosthesis.    
     
     
         10 . The curable composition of    claim 9   , wherein the polymerization system includes a polymerizable monomer or prepolymer, a crosslinking agent, a filler and a polymerization initiator.  
     
     
         11 . The curable composition of    claim 10   , wherein the polymerizable monomer is selected from the group consisting of methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, hydroxybutyl methacrylate, propylene glycol monomethacrylate, poly(ethylene glycol) monomethacrylate, isobornyl acrylate, isobornyl methacrylate, methoxyethoxyethyl methacrylate, ethoxyethoxyethyl methacrylate, tetrahydrofurfuryl methacrylate, and acetoxyethyl methacrylate.  
     
     
         12 . The curable composition of    claim 11   , wherein the prepolymer is selected from the group consisting of 2,2-bis[4′-(3″-methacryloyl-2″-hydroxypropoxy)phenyl]propane (bis-GMA), ethoxylated bisphenol A dimethacrylate, and urethane dimethacrylate.  
     
     
         13 . The curable composition of    claim 12   , wherein the crosslinking agent is selected from the group consisting of ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, trimethylene glycol dimethacrylate, trimethyolpropane trimethacrylate, 1,4-butanediol dimethacrylate, 1,12-dodecanediol dimethacrylate, and polyethylene glycol dimethacrylate.  
     
     
         14 . The curable composition of    claim 13   , wherein the filler is a finely divided material or powder and is a member selected from the group consisting of quartz, colloidal silica, alumina, hydroxyapatite, fluoroaluminosilicate glass, titanium dioxide, pyrogenic silica, precipitated silica, glasses, ceramics, poly(methyl methacrylate), poly(ethyl methacrylate), poly(butyl methacrylate), poly(ethyl-co-methyl methacrylate), poly (methyl vinyl ether-co-maleic anhydirde), poly(acrylic acid), poly(methacrylic acid), poly(vinyl pyrollidone), poly(vinyl acetate), poly(vinyl butyryl), polyethylene, polypropylene, and polytetrafluoroethylene.  
     
     
         15 . The curable composition of    claim 14   , wherein the polymerization initiator is a member selected from the group consisting of benzoyl peroxide, lauroyl peroxide, 5-alkyl barbituric acid, and 5-aryl barbituric acid.  
     
     
         16 . The curable composition of    claim 9   , wherein the water-insoluble antimicrobial agent is a member selected from the group consisting of halogenated diphenyl ethers, halogenated salicylanilides, benzoic esters, halogenated carbanalides, and phenolic compounds.  
     
     
         17 . The curable composition of    claim 9   , wherein the curable composition is fashioned into an oral prosthesis.  
     
     
         18 . The curable composition of    claim 17   , wherein the oral prosthesis is a denture or filling.  
     
     
         19 . The curable composition of    claim 9   , wherein the curable composition is fashioned into an artificial fingernail or artificial toenail.  
     
     
         20 . The curable composition of    claim 9   , wherein the water-insoluble antimicrobial agent is initially present in an amount greater than 0.1% by weight of the artificial prosthesis.  
     
     
         21 . The curable composition of    claim 9   , wherein the water-insoluble antimicrobial agent is initially present in an amount between about 0.1% and 4% by weight of the artificial prosthesis.  
     
     
         22 . The curable composition of    claim 9   , wherein the water-insoluble antimicrobial agent is initially present in an amount less than 4% by weight of the artificial prosthesis.  
     
     
         23 . A method for inhibiting the growth of bacteria associated with a human in an area directly adjacent to a hardened artificial prosthesis comprising: 
 fashioning a hardened artificial prosthesis including a water-insoluble antimicrobial agent;    placing the artificial prosthesis in an aqueous environment susceptible to the growth of bacteria;    allowing the artificial prosthesis to establish a zone of inhibition in a manner to inhibit the growth of bacteria within the zone of inhibition.    
     
     
         24 . The method of    claim 23   , wherein the bacteria is  S. mutans  or  P. Aeruginosa.    
     
     
         25 . The method of    claim 23   , wherein the water-insoluble antimicrobial agent is initially present in an amount greater than 0.1% by weight of the artificial prosthesis.  
     
     
         26 . The method of    claim 23   , wherein the water-insoluble antimicrobial agent is initially present in an amount between about 0.1% and 4% by weight of the artificial prosthesis.  
     
     
         27 . The method of    claim 23   , wherein the water-insoluble antimicrobial agent is initially present in an amount less than 4% by weight of the artificial prosthesis.  
     
     
         28 . An artificial prosthesis for use in an aqueous environment comprising: 
 a mixture of a polymerization system and a water-insoluble agent which remains inert to the polymerization system;    the mixture capable of being cured to produce an artificial prosthesis characterized as having a zone of inhibition of growth of bacteria surrounding the artificial prosthesis.    
     
     
         29 . An artificial fingernail comprising: 
 a mixture of a polymerization system and a water-insoluble antimicrobial agent which remains inert to the polymerization system;    the mixture capable of being cured to produce an artificial fingernail characterized as having a zone of inhibition of growth of bacteria surrounding the artificial prosthesis.    
     
     
         30 . A method of preventing demineralization of surface enamel on a tooth comprising fashioning a hardened artificial prosthesis including a water-insoluble antimicrobial agent; 
 placing the artificial prosthesis adjacent the tooth;    allowing the artificial prosthesis to establish a zone of inhibition in a manner to inhibit growth of bacteria within the zone of inhibition so as to prevent demineralization of the tooth.