Meniscal Repair Adhesive

Abstract

A composition that includes (a) a prepolymer having at least one free isocyanate group that is capable of bonding to tissue and that cures in vivo upon exposure to water to form a polymer having a compressive modulus between 1.9 and 14.4 MPa and a tensile modulus between 5.0 and 30, and (b) an oil that is miscible in the prepolymer, the oil being selected from the group consisting of silicone oils, mineral oil, vegetable oils, and combinations thereof. The composition retains its integrity when delivered in an aqueous medium.

What is claimed is: 
     
         1 . A composition comprising:
 (a) a prepolymer having at least one free isocyanate group that is capable of bonding to tissue and that cures in vivo upon exposure to water to form a polymer having a compressive modulus between 1.9 and 14.4 MPa and a tensile modulus between 5.0 and 30, and   (b) an oil that is miscible in the prepolymer, the oil being selected from the group consisting of silicone oils, mineral oil, vegetable oils, and combinations thereof, wherein the composition retains its integrity when delivered in an aqueous medium.   
     
     
         2 . A composition according to  claim 1  wherein the prepolymer comprises linkages selected from the group consisting of urea linkages, urethane linkages, and combinations thereof. 
     
     
         3 . A composition according to  claim 1  wherein the prepolymer is a siloxane prepolymer. 
     
     
         4 . A composition according to  claim 3  wherein the siloxane prepolymer has the formula: 
       
         
           
           
               
               
           
         
         where n is 1 to 10; x and y, independently, are 2 to 10; R 1 , R 2 , R 3 , R 5 , and R 6 , independently, are selected from the group consisting of hydroxyl groups; straight chain, branched, or cyclic C 1 -C 6  alkyl groups that may be substituted with one or more isocyanate groups; straight chain, branched, or cyclic C 1 -C 6  fluorinated alkyl groups that may be substituted with one or more isocyanate groups; and combinations thereof; R 4  is selected from the group consisting of —NCO, —SH, —OH, R 7 N + X—; R 7  is a straight chain, branched, or cyclic C 1 -C 6  alkyl group; and X is selected from the group consisting of F, Cl, Br, and I, with the proviso that at least one of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  includes an isocyanate group. 
       
     
     
         5 . A composition according to  claim 3  wherein the siloxane prepolymer has the formula: 
       
         
           
           
               
               
           
         
         where R 1  and R 2 , independently, are selected from the group consisting of hydroxyl groups; straight chain, branched, or cyclic C 1 -C 6  alkyl groups that may be substituted with one or more isocyanate groups; straight chain, branched, or cyclic C 1 -C 6  fluorinated alkyl groups that may be substituted with one or more isocyanate groups; and combinations thereof. 
       
     
     
         6 . A composition according to  claim 1  wherein the prepolymer comprises the reaction product of a polyisocyanate and an active hydrogen component selected from the group consisting of polyols, polyamines, polythiols, polycarboxylic acids, and combinations thereof. 
     
     
         7 . A composition according to  claim 1  wherein the prepolymer comprises the reaction product of (a) a polyisocyanate, (b) an active hydrogen component selected from the group consisting of polyols, polyamines, polythiols, polycarboxylic acids, and combinations thereof, and (c) an ionic salt or amino acid component having an average hydroxyl or amino functionality, or combination thereof, of at least 1. 
     
     
         8 . A composition according to  claim 7  wherein the ionic salt component is selected from the group consisting of ammoniates, halides, sulfonates, phosphonates, carboxylates, and combinations thereof. 
     
     
         9 . A composition according to  claim 1  wherein the composition comprises at least two different prepolymers. 
     
     
         10 . A composition according to  claim 8  wherein the prepolymers are selected from the group of compounds having the formulae: 
       
         
           
           
               
               
           
         
         and combinations thereof. 
       
     
     
         11 . A composition according to  claim 1  wherein the oil comprises a silicone oil. 
     
     
         12 . A composition according to  claim 11  wherein the silicone oil is selected from the group consisting of polydimethylsiloxane, simethicone, and combinations thereof. 
     
     
         13 . A composition according to  claim 1  wherein the tissue is selected from the group consisting of meniscal tissue, cartilage, tendons, and combinations thereof. 
     
     
         14 . A method of repairing a defect in meniscal tissue comprising delivering a composition according to  claim 1  to the knee joint in an aqueous environment in the area of the meniscal defect, and allowing the composition to cure and bond to the meniscal tissue.