Antimicrobial Thermoplastic Polyuethanes

Abstract

The disclosed technology provides thermoplastic polyurethane compositions having non-leaching antimicrobial properties while still maintaining good physical properties, methods of making the same, and articles, including medical devices, made from such compositions. The disclosed technology includes a process of making an antimicrobial polymer composition, where the process includes mixing an antimicrobial additive into a polymeric material; wherein said polymeric material comprises a polymeric backbone made up of urethane linkages derived from a polyisocyanate and a polyol; and wherein said mixing occurs under conditions that result in the breaking of a minority of said urethane bonds resulting in reactive isocyanate groups; and wherein two or more of said reactive isocyanate groups react with said antimicrobial additive to covalently bond said antimicrobial additive into the polymeric backbone of said polymeric material; resulting in an antimicrobial polymer composition.

What is claimed is: 
     
         1 . A process of making an antimicrobial polymer composition, said process comprising the steps of:
 a) mixing an antimicrobial additive into a polymeric material, wherein said antimicrobial additive comprises a deprotonated guanidine compound, a deprotonated biguanidine compound, or a mixture thereof;   wherein said polymeric material comprises a polymeric backbone made up of urethane linkages derived from a polyisocyanate and a polyol; and   wherein said mixing occurs under conditions that result in the breaking of a minority of said urethane bonds resulting in reactive isocyanate groups; and   wherein two or more of said reactive isocyanate groups react with said antimicrobial additive to covalently bond said antimicrobial additive into the polymeric backbone of said polymeric material;   resulting in an antimicrobial polymer composition.   
     
     
         2 . (canceled) 
     
     
         3 . The process of  claim 1  wherein said antimicrobial additive comprises deprotonated polyhexamethylene biguanide. 
     
     
         4 . The process of  claim 1  wherein said polymeric material comprises a thermoplastic polyurethane derived from (a) a polyisocyanate component, (b) a polyol component, and (c) an optional chain extender component. 
     
     
         5 . (canceled) 
     
     
         6 . The process of  claim 1  wherein said mixing occurs at a temperature between 180 and 225 degrees Celsius. 
     
     
         7 . The process of  claim 1  wherein said mixing occurs in an extruder where the antimicrobial additive is added to the polymeric material and wherein said mixing occurs at a temperature between 180 and 225 degrees Celsius, where the extruder comprises a twin screw extruder with co-rotating, self-wiping screws, with a mixture of conveying and mixing elements, and a length to diameter ratio of 30:1 to 50:1. 
     
     
         8 . The process of  claim 1  wherein said antimicrobial additive comprises a deprotonated guanidine compound, a deprotonated biguanidine compound, or a mixture thereof;
 wherein said reactive isocyanate groups reacts with said antimicrobial additive and said polymeric material to covalently bond said antimicrobial additive to the polymeric backbone of said polymeric material; and 
 wherein said mixing occurs at a temperature between 180 and 225 degrees Celsius. 
 
     
     
         9 . The process of  claim 1  wherein said antimicrobial additive comprises polyhexamethylene biguanide, deprotonated polyhexamethylene biguanide, or a combination thereof;
 wherein said polymeric material comprises a thermoplastic polyurethane derived from (a) a diisocyanate, (b) an aromatic polyether polyol, and (c) a butane diol component. 
 wherein said mixing occurs in an extruder where the antimicrobial additive is added to the polymeric material and wherein said mixing occurs at a temperature between 180 and 225 degrees Celsius, where the extruder comprises a twin screw extruder with co-rotating, self-wiping screws, with a mixture of conveying and mixing elements, and a length to diameter ratio of 30:1 to 50:1. 
 
     
     
         10 . The process of  claim 1  wherein the resulting antimicrobial polymer composition is non-leaching as determined by the AATCC 147 Assessment of Antimicrobial Finishes on Textile Materials: Parallel Streak Method. 
     
     
         11 . An antimicrobial polymer composition comprising a polymeric material and an antimicrobial additive selected from the group consisting of guanide and biguanide,
 wherein said polymeric material comprises a polymeric backbone comprising urethane linkages derived from a polyisocyanate and a polyol; and   wherein said antimicrobial additive is covalently bonded into said polymeric backbone of the polymeric material by two or more linkages between the nitrogen atoms of the guanide or biguanide and the isocyanate.   
     
     
         12 . The antimicrobial polymer composition of  claim 11  wherein said antimicrobial additive comprises a deprotonated guanidine compound, a deprotonated biguanidine compound, or a mixture thereof;
 wherein said polymeric material comprises a thermoplastic polyurethane derived from (a) a diisocyanate, (b) a polyether polyol, and (c) a butane diol component. 
 
     
     
         13 . An article comprising an antimicrobial polymer composition,
 wherein said antimicrobial polymer composition comprises a polymeric material and an antimicrobial additive selected from the group consisting of guanide and biguanide,   wherein said polymeric material comprises a polymeric backbone comprising urethane linkages derived from a polyisocyanate and a polyol; and   wherein said antimicrobial additive is covalently bonded into said polymeric backbone of the polymeric material by two or more isocyanate linkages.   
     
     
         14 . The article of  claim 13  wherein said antimicrobial additive comprises a deprotonated guanidine compound, a deprotonated biguanidine compound, or a mixture thereof;
 wherein said polymeric material comprises a thermoplastic polyurethane derived from (a) a diisocyanate, (b) a polyether polyol, and (c) butane diol component. 
 
     
     
         15 . The article of  claim 13 , wherein the antimicrobial polymer composition is coated onto a material forming the article.