Gel materials, medical articles, and methods

Abstract

A gel material and medical articles including such material, wherein the transparent gel material includes a polymerized poly(alkylene oxide) macromonomer that, prior to polymerization, is free-radically polymerizable, multifunctional (preferably difunctional), and has an average molecular weight of at least about 2000.

1 . A medical article comprising a gel material comprising: 
 a homopolymer or copolymer of a multifunctional poly(alkylene oxide) free-radically polymerizable macromonomer having a weight average molecular weight of at least about 2000, wherein the multifunctional poly(alkylene oxide) macromonomer comprises a copolymeric random alkylene oxide moiety of the formula:      —(—CH(R 1 )—CH 2 —O—) m  . . . (—CH 2 —CH 2 —O—) n —   wherein the mole ratio of m:n is within a range of about 1:9 to about 9:1; and R 1  is a (C1-C4)alkyl group.    
   
   
       2 . The medical article of  claim 1  wherein the gel material comprises a homopolymer of the multifunctional poly(alkylene oxide) macromonomer.  
   
   
       3 . The medical article of  claim 1  wherein the multifunctional macromonomer is a difunctional macromonomer of the formula:  
       XO—(—CH(R 1 )—CH 2 —O—) m  . . . (—CH 2 —CH 2 —O—) n —Y  
     wherein: the mole ratio of m:n is within a range of about 1:9 to about 9:1; and R 1  is a (C1-C4)alkyl group; and X and Y are each independently selected from the group consisting of  
     
       
         
         
             
             
         
       
     
     wherein R 2  is H or CH 3 , R 3  is an aromatic group, aliphatic group, alicylic group, or combinations thereof, W is an alkylene or alkylene oxide group, and r=2-10.  
   
   
       4 . The medical article of  claim 1  wherein the gel material comprises a copolymer of the multifunctional poly(alkylene oxide) macromonomer.  
   
   
       5 . The medical article of  claim 4  wherein the multifunctional macromonomer is a difunctional macromonomer of the formula:  
       XO—(—CH(R 1 )—CH 2 —O—) m  . . . (—CH 2 —CH 2 —O—) n —Y  
     wherein: the mole ratio of m:n is within a range of about 1:9 to about 9:1; and R 1  is a (C1-C4)alkyl group; and X and Y are each independently selected from the group consisting of  
     
       
         
         
             
             
         
       
     
     wherein R 2  is H or CH 3 , R 3  is an aromatic group, aliphatic group, alicylic group, or combinations thereof, W is an alkylene or alkylene oxide group, and r=2-10.  
   
   
       6 . The medical article of  claim 5  wherein R 1  is methyl, the mole ratio of m:n is about 1:3, and X and Y are each independently  
     
       
         
         
             
             
         
       
     
     wherein R 2  is CH 3 .  
   
   
       7 . The medical article of  claim 5  wherein the gel material comprises a copolymer of the multifunctional poly(alkylene oxide) macromonomer and a monofunctional poly(alkylene oxide) monomer.  
   
   
       8 . The medical article of  claim 5  wherein the gel material comprises a copolymer of the multifunctional poly(alkylene oxide) macromonomer and a polar monomer.  
   
   
       9 . The medical article of  claim 5  comprising a copolymer of the multifunctional macromonomer, a polar monomer, a monofunctional poly(alkylene oxide) monomer, and a hydrophobic monomer.  
   
   
       10 . The medical article of  claim 1  wherein the multifunctional macromonomer is difunctional.  
   
   
       11 . The medical article of  claim 10  wherein the multifunctional macromonomer is linear.  
   
   
       12 . A medical article comprising a gel material comprising a homopolymer or copolymer prepared from monomers comprising: 
 about 5 wt-% to 100 wt-% of a multifunctional poly(alkylene oxide) free-radically polymerizable macromonomer having a weight average molecular weight of at least about 2000, wherein the multifunctional poly(alkylene oxide) macromonomer comprises a copolymeric alkylene oxide moiety of the formula:      —(—CH(R 1 )—CH 2 —O—) m  . . . (—CH 2 —CH 2 —O—) n —   wherein the mole ratio of m:n is within a range of about 1:9 to about 9:1; and R 1  is a (C1-C4)alkyl group;    0 wt-% to about 80 wt-% of a monofunctional poly(alkylene oxide) monomer; and    0 wt-% to about 40 wt-% of a polar monomer.    
   
   
       13 . The medical article of  claim 12  which is a wound dressing or wound packing.  
   
   
       14 . The medical article of  claim 12  wherein the gel material is transparent and absorbent.  
   
   
       15 . A multifunctional macromonomer comprising a copolymeric random alkylene oxide moiety of the formula:  
       XO—(—CH(R 1 )—CH 2 —O—) m  . . . (—CH 2 —CH 2 —O—) n —Y  
     wherein the mole ratio of m:n is within a range of about 1:9 to about 9:1, R 1  is a (C1-C4)alkyl group, and X and Y are independently selected from the group consisting of  
     
       
         
         
             
             
         
       
     
     wherein R 2  is H or CH 3 , R 3  is an aromatic group, aliphatic group, alicylic group, or combinations thereof, and W is an alkylene or alkylene oxide group.  
   
   
       16 . A multifunctional macromonomer comprising a copolymeric random alkylene oxide moiety of the formula:  
       —(—CH(R 1 )—CH 2 —O—) m  . . . (—CH 2 —CH 2 —O—) n — 
     wherein the mole ratio of m:n is within a range of about 1:9 to about 9:1 and R 1  is a (C1-C4)alkyl group; 
 and wherein the macromonomer comprises two or more end groups selected from the group consisting of  
                     
 and mixtures thereof, wherein R 2  is H or CH 3 , R 3  is an aromatic group, aliphatic group, alicylic group, or combinations thereof, and W is an alkylene or alkylene oxide group.  
 
   
   
       17 . A multifunctional macromonomer having a molecular weight of at least about 2000, wherein the multifunctional macromonomer comprises a copolymeric random alkylene oxide moiety of the formula:  
       XO—(—CH(R 1 )—CH 2 —O—) m  . . . (—CH 2 —CH 2 —O—) n —Y  
     wherein the mole ratio of m:n is within a range of about 1:9 to about 9:1, R 1  is a (C1-C4)alkyl group, and X and Y are independently selected from the group consisting of  
     
       
         
         
             
             
         
       
     
     wherein R 2  is H or Me and r=2-10.  
   
   
       18 . A multifunctional macromonomer having a molecular weight of at least about 2000, wherein the multifunctional macromonomer comprises a copolymeric random alkylene oxide moiety of the formula:  
       —(—CH(R 1 )—CH 2 —O—) m  . . . (—CH 2 —CH 2 —O—) n — 
     wherein the mole ratio of m:n is within a range of about 1:9 to about 9:1 and R 1  is a (C 1 -C 4 )alkyl group; 
 and wherein the macromonomer comprises two or more end groups selected from the group consisting of  
                     
 and mixtures thereof, wherein R 2  is H or Me and r=2-10.  
 
   
   
       19 . A polymer prepared from the macromonomer of  claim 15 .  
   
   
       20 . A polymer prepared from the macromonomer of  claim 16 .  
   
   
       21 . A polymer prepared from the macromonomer of  claim 17 .  
   
   
       22 . A polymer prepared from the macromonomer of  claim 18 .  
   
   
       23 . A syrup polymer mixture comprising a partially polymerized homopolymer or copolymer prepared from monomers comprising: 
 about 0.1 wt-% to 100 wt-% of a multifunctional poly(alkylene oxide) free-radically polymerizable macromonomer having a weight average molecular weight of at least about 2000, wherein the multifunctional poly(alkylene oxide) macromonomer comprises a copolymeric alkylene random oxide moiety of the formula:      —(—CH(R 1 )—CH 2 —O—) m  . . . (—CH 2 —CH 2 —O—) n —   wherein the mole ratio of m:n is within a range of about 1:9 to about 9:1; and R 1  is a (C1-C4)alkyl group;    0 wt-% to about 80 wt-% of a monofunctional poly(alkylene oxide) monomer;    0 wt-% to about 40 wt-% of a polar monomer; and    0 wt-% to about 20 wt-% of a hydrophobic monomer.    
   
   
       24 . A method of making a gel, the method comprising 
 forming a syrup polymer mixture comprising a partially polymerized homopolymer or copolymer prepared from monomers comprising: 
 about 0.1 wt-% to 100 wt-% of a multifunctional poly(alkylene oxide) free-radically polymerizable macromonomer having a weight average molecular weight of at least about 2000, wherein the multifunctional poly(alkylene oxide) macromonomer comprises a copolymeric alkylene random oxide moiety of the formula:  
   —(—CH(R 1 )—CH 2 —O—) m  . . . (—CH 2 —CH 2 —O—) n — 
 wherein the mole ratio of m:n is within a range of about 1:9 to about 9:1; and R 1  is a (C1-C4)alkyl group;  
 0 wt-% to about 80 wt-% of a monofunctional poly(alkylene oxide) monomer;  
 0 wt-% to about 40 wt-% of a polar monomer; and  
 0 wt-% to about 20 wt-% of a hydrophobic monomer; and  
   forming a gel from the syrup polymer mixture.    
   
   
       25 . The method of  claim 24  wherein the syrup polymer mixture comprises a photo initiator.  
   
   
       26 . The method of  claim 25  wherein the step of forming a gel from the syrup polymer mixture comprises applying radiation.  
   
   
       27 . The method of  claim 24  wherein the step of forming a gel from the syrup polymer mixture comprises applying thermal energy.  
   
   
       28 . The method of  claim 25  wherein the step of forming a gel from the syrup polymer mixture comprises applying ultraviolet radiation and thermal energy sequentially.