Anti-microbial particles and methods of use thereof

Abstract

This invention relates to anti-microbial active particles, compositions and uses thereof for inhibiting bacterial growth on surfaces or devices. This invention further discloses methods of making such anti-microbial active particles.

1 . A dental restorative composite comprising (i) a polymeric material and (ii) anti-microbial particles which are represented by structure (1): 
       
         
           
           
               
               
           
         
       
       wherein 
       the core is an inorganic material; 
       L 1  is a first linker; 
       L 2  is a second linker; 
       L 3  is a bond or a third linker; 
       R 1  and R 1 ′ are each independently alkyl, terpenoid, cycloalkyl, aryl, heterocycle, alkenyl, alkynyl or any combination thereof; 
       R 2  and R 2 ′ are each independently alkyl, terpenoid, cycloalkyl, aryl, heterocycle, alkenyl, alkynyl or any combination thereof; 
       R 3  and R 3 ′ are each independently not present, hydrogen, alkyl, terpenoid moiety, cycloalkyl, aryl, heterocycle, alkenyl or alkynyl; wherein if R 3  or R 3 ′ is not present, then the nitrogen is not charged; 
       X 1  and X 2  is each independently a bond, alkylene, alkenylene, or alkynylene;
 p defines the surface density of anti-microbial active units per square nanometer (nm 2 ) of the core surface, wherein said surface density is between 1-100 anti-microbial active groups per one square nanometer (nm 2 ) of the core surface of the particle; 
 
       n 1  is each independently an integer between 0 to 200; 
       n 2  is each independently an integer between 0 to 200; 
       wherein n 1 +n 2 ≥2; 
       m is an integer between 1 to 200 and the repeating unit is the same or different; and 
       wherein the number of the anti-microbial active groups per each anti-microbial active unit is between 2-200; and 
       wherein said composite is used in dental applications. 
     
     
         2 . The composite of  claim 1 , wherein the particles are dispersed in the polymeric material. 
     
     
         3 . The composite of  claim 1 , wherein the particles are represented by structure (2): 
       
         
           
           
               
               
           
         
       
     
     
         4 . The composite of  claim 1 , wherein the particles are represented by structure (3): 
       
         
           
           
               
               
           
         
       
     
     
         5 . The composite of  claim 1 , wherein the core of the particles comprises silica. 
     
     
         6 . The composite of  claim 5 , wherein the silica is selected from the group consisting of amorphous silica, dense silica, aerogel silica, porous silica, mesoporous silica and fumed silica. 
     
     
         7 . The composite of  claim 1 , wherein the polymeric material is selected from the group consisting of organic polymers, inorganic polymers and combinations thereof. 
     
     
         8 . The composite of  claim 7 , wherein the organic polymer is selected from the group consisting of polyolefins, epoxy resin, acrylate resin and combinations thereof. 
     
     
         9 . The composite of  claim 7 , wherein the inorganic polymer is selected from the group consisting of silicone polymers ceramics, metals and combinations thereof. 
     
     
         10 . 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%. 
     
     
         11 . The composite of  claim 1 , wherein the particles are a mixture of different particles. 
     
     
         12 . 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. 
     
     
         13 . The composite of  claim 1 , intended to inhibit or prevent biofilm formation or growth onto the dental restorative composite. 
     
     
         14 . 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. 
     
     
         15 . The composite  claim 1 , wherein the anti-microbial active groups have a surface density of 50-100 anti-microbial groups per 1 square nm of the core surface. 
     
     
         16 . The composite of  claim 1 , wherein the anti-microbial particles are presented by the following structure: 
       
         
           
           
               
               
           
         
       
       wherein n=2-200; and 
       p defines the surface density of the oligomeric/polymeric anti-microbial active units per one sq nm (nm 2 ) of the core surface, wherein said density is of between 1-20 anti-microbial active units per one sq nm (nm 2 ) of the core surface of the particle. 
     
     
         17 . The composite of  claim 1 , wherein the inorganic core is polyhedral oligomeric silsesquioxane (POSS).