Compositions and medical devices comprising anti-microbial particles

Abstract

This invention relates to compositions and medical devices comprising anti-microbial active particles, for inhibiting microbial growth. This invention further provides methods of making such compositions and medical devices.

What is claimed is: 
     
         1 . A dental restorative composite comprising (i) a polymeric material and (ii) an anti-microbial particles which are represented by structure (1): 
       
         
           
           
               
               
           
         
         wherein 
         the core is an inorganic material; 
         L1 is a first linker or a bond; 
         L2 is a second linker; 
         L3 is a third linker or a bond; 
         R1 and R1′ are each independently unsubstituted C1-C10 alkyl, terpenoid, cycloalkyl, aryl, heterocycle, alkenyl, alkynyl or any combination thereof, 
         R2 and R2′ are each independently unsubstituted C1-C10 alkyl, terpenoid, cycloalkyl, aryl, heterocycle, alkenyl, alkynyl or any combination thereof, 
         R3 and R3′ are each independently not present, hydrogen, C4-C8 alkyl, terpenoid moiety, cycloalkyl, aryl, heterocycle, alkenyl, or alkynyl; wherein if R3 or R3′ are not present, the nitrogen is not charged; 
         X1 and X2 is each independently a bond, alkylene, alkenylene, or alkynylene; 
         p defines the density of anti-microbial active unit per one square nm (nm 2 ) of the core surface, wherein said density is of between 1-100 anti-microbial active units per one square nm (nm 2 ) of the core surface of the particle; 
         n 1  an integer 0 or 1; 
         n 2  is an integer 0 or 1; 
         m is an integer 1; and 
         wherein said composite is used in dental applications. 
       
     
     
         2 . The composite of  claim 1 , wherein the particle is represented by Structure (4): 
       
         
           
           
               
               
           
         
         wherein 
         X′ is nothing or hydrogen; 
         wherein at least one of R 1 , R 2 , R 3  is hydrophobic having at least four carbons. 
       
     
     
         3 . The composite of  claim 1 , wherein the particles are dispersed in the polymeric material. 
     
     
         4 . The composite of  claim 1 , wherein the core of the particles comprises silica. 
     
     
         5 . The composite of  claim 4 , wherein the silica is selected from the group consisting of amorphous silica, dense silica, aerogel silica, porous silica, mesoporous silica and fumed silica. 
     
     
         6 . The composite of  claim 1 , wherein the inorganic polymer is selected from the group consisting of silicone polymers ceramics, metals, and combinations thereof. 
     
     
         7 . The composite of  claim 1 , wherein the inorganic core is polyhedral oligomeric silsesquioxane (POSS). 
     
     
         8 . The composite of  claim 1 , wherein the weight ratio of the anti-microbial particles which are represented by structure (1) to the polymeric material is between 0.25-5%. 
     
     
         9 . The composite of  claim 1 , wherein the particles are a mixture of different particles. 
     
     
         10 . The composite of  claim 1 , wherein said composition is capable of filling of tooth decay cavities, is a dental restorative endodontic filling material for filling root canal space in root canal treatment, or is selected from the group consisting of a dental restorative material intended for provisional and final tooth restorations or tooth replacement, a dental inlay, a dental onlay, a crown, a partial denture, a complete denture, a dental implant, a dental implant abutment, and a cement intended for permanently cementing crowns bridges, onlays, partial dentures and orthodontic appliances onto tooth enamel and dentin. 
     
     
         11 . The composite of  claim 1 , wherein the anti-microbial active groups have a surface density of 1-20 anti-microbial groups per 1 square nm of the core surface. 
     
     
         12 . The composite  claim 1 , wherein the anti-microbial active groups have a surface density of 50-100 anti-microbial groups per square nm of the core surface. 
     
     
         13 . The composite of  claim 1 , wherein said composite is prepared by mixing Bis-GMA (bisphenol A-glycidyl methacrylate); UDMA (urethane dimethacrylate); TEGDMA (triethyleneglycol dimethacrylate); Camphorquinine; Ethyl-4-dimethylamino benzoate (EDMAB); Fumed silica; Silanated glass fille; and the anti-microbial particles represented by structure (1). 
     
     
         14 . The composite of  claim 13 , wherein the components of said mixture are in the following amounts:
 Bis-GMA: 10% wt.;   UDMA: 5% wt.;   TEGDMA: 5% wt.;   Camphorquinine: 1% wt.;   EDMAB: 1% wt.;   Fumed silica: 5% wt.;   Silanated glass filler: 73% wt.; and   the anti-microbial particles represented by structure (1): 2% wt.