Antimicrobial shape memory polymers

Abstract

An embodiment includes a system comprising a thermoset polyurethane shape memory polymer (SMP) foam that includes at least one antimicrobial agent. The antimicrobial agent may include at least one phenolic acid that is a pendent group chemically bonded to a polyurethane polymer chain of the SMP foam. Other embodiments are described herein.

What is claimed is: 
     
         1 . A method comprising:
 reacting a first polyol portion with an antimicrobial agent to form a first reaction product;   reacting a first portion of the first reaction product with a second polyol portion and an isocyanate to form a second reaction product;   reacting the second reaction product with a second portion of the first reaction product and a third polyol portion to form a third reaction product; and   mixing the third reaction product with a blowing agent to form a shape memory polymer (SMP) foam;   wherein the SMP foam is a thermoset polyurethane SMP foam.   
     
     
         2 . The method of  claim 1 , wherein the at least one antimicrobial agent includes a phenolic acid. 
     
     
         3 . The method of  claim 2 , wherein the phenolic acid includes at least one of cinnamic acid, benzoic acid, gentisic acid, 4-hydroxy benzoic acid, p-coumaric acid, vanillic acid, syringic acid, protocatechuic acid, gallic acid, ferulic acid, sinapic acid, caffeic acid, or combinations thereof. 
     
     
         4 . The method of  claim 1 , wherein the reacting the first polyol portion with the antimicrobial agent to form the first reaction product comprises esterification of the antimicrobial agent. 
     
     
         5 . The method of  claim 1 , wherein the first reaction product comprises a triol. 
     
     
         6 . The method of  claim 1 , wherein:
 at least one of the first, second, and third polyol portions includes at least one of triethanolamine (TEA), diethanolamine, butane diol, butyne diol, N,N,N′,N′ tetrakis (hydroxyl propylene) ethylenediamine (HPED), or combinations thereof; and   the isocyanate includes at least one of hexamethylene diisocyanate (HDI), trimethyl hexamethylene diisocyanate (TMHDI), isophorone diisocyanate (IPDI), or combinations thereof.   
     
     
         7 . The method of  claim 6 , wherein the antimicrobial agent includes at least one of a phenolic acid, a fluorescent dye, a metal, or combinations thereof. 
     
     
         8 . The method of  claim 7 , wherein the at least one antimicrobial agent includes the phenolic acid. 
     
     
         9 . The method of  claim 8 , wherein the phenolic acid includes at least one of cinnamic acid, benzoic acid, gentisic acid, 4-hydroxy benzoic acid, p-coumaric acid, vanillic acid, syringic acid, protocatechuic acid, gallic acid, ferulic acid, sinapic acid, caffeic acid, or combinations thereof. 
     
     
         10 . The method of  claim 8 , wherein the phenolic acid is a pendent group chemically bonded to a polyurethane polymer chain of the SMP foam. 
     
     
         11 . The method of  claim 6 , wherein the antimicrobial agent includes a carboxylic acid group. 
     
     
         12 . The method of  claim 6 , wherein the SMP foam is included in a wound dressing. 
     
     
         13 . The method of  claim 6 , wherein the second reaction product is a prepolymer formed before mixing the third reaction product with the blowing agent. 
     
     
         14 . The method of  claim 1 , wherein the antimicrobial agent includes a carboxylic acid group. 
     
     
         15 . The method of  claim 1 , wherein the antimicrobial agent includes at least one phenolic acid that is a pendent group chemically bonded to a polyurethane polymer chain of the SMP foam. 
     
     
         16 . The method of  claim 15 , wherein the pendent group is chemically bonded to the polyurethane polymer chain via an ester. 
     
     
         17 . The method of  claim 1 , wherein the second reaction product is a prepolymer formed before mixing the third reaction product with the blowing agent. 
     
     
         18 . The method of  claim 1 , wherein the SMP foam is included in a wound dressing. 
     
     
         19 . A method comprising:
 reacting a first polyol portion with a first antimicrobial agent portion and an isocyanate to form a first reaction product;   reacting the first reaction product with a second polyol portion and a second antimicrobial agent portion to form a second reaction product;   mixing the second reaction product with a blowing agent to form a shape memory polymer (SMP) foam;   wherein the SMP foam is a thermoset polyurethane SMP foam;   wherein the first reaction product is a prepolymer formed before mixing the second reaction product with the blowing agent to form the SMP foam.   
     
     
         20 . The method of  claim 19 , wherein the antimicrobial agent includes at least one phenolic acid.