Curing Accelerator and Method of Making

Abstract

The invention concerns sterilized cyanoacrylate adhesive compositions comprising 99% or more by weight, based on the weight of the adhesive composition, of 2-octyl cyanoacrylate, mixed together with butylated hydroxyl anisole, sulfur dioxide, and 100 to 1000 parts per million, based on the weight of the adhesive composition, of a 18-crown-6 crown ether, wherein the composition is sterilized by irradiation as well as methods of making and using such compositions.

1 . (canceled) 
     
     
         2 . A sterilized cyanoacrylate adhesive composition, comprising
 99% or more by weight, based on the weight of the adhesive composition, of 2-octyl cyanoacrylate, mixed together with   free radical stabilizer,   anionic vapor phase stabilizer, and   100 to 1000 parts per million, based on the weight of the adhesive composition, of a 18-crown-6 crown ether,   wherein the composition is sterilized by irradiation, and
 wherein the sterilized cyanoacrylate adhesive composition does not cure upon sterilization. 
   
     
     
         3 . The sterilized cyanoacrylate adhesive composition of  claim 2 , wherein the adhesive remains fluid following storage for twelve days at 80° C. 
     
     
         4 . The sterilized cyanoacrylate adhesive composition of  claim 2 , wherein the anionic vapor phase stabilizer is present in the composition at a concentration of less than 20 parts per million. 
     
     
         5 . The sterilized cyanoacrylate adhesive composition of  claim 2 , wherein the free radical stabilizer is butylated hydroxyl anisole. 
     
     
         6 . The sterilized cyanoacrylate adhesive composition of  claim 2 , wherein the anionic vapor phase stabilizer is sulfur dioxide. 
     
     
         7 . The sterilized cyanoacrylate adhesive composition of  claim 2 , further comprising therapeutic-loaded nanoparticles. 
     
     
         8 . The sterilized cyanoacrylate adhesive composition of  claim 2 , wherein the composition has been treated with a particulate agent selected from the group consisting of vinyl pyrrolidone polymers and co-polymers. 
     
     
         9 . The sterilized cyanoacrylate adhesive composition of  claim 2 , wherein the irradiation is gamma irradiation, electron beam irradiation, microwave irradiation, or ultraviolet radiation. 
     
     
         10 . A kit, comprising the sterilized cyanoacrylate adhesive composition of  claim 2  and an applicator. 
     
     
         11 . The kit of  claim 10 , wherein said sterilized cyanoacrylate adhesive composition has been treated with a particulate agent chosen from the group consisting of vinyl pyrrolidone polymers and co-polymers. 
     
     
         12 . The kit of  claim 10 , wherein the anionic vapor phase stabilizer is present in the composition at a concentration of less than 20 parts per million. 
     
     
         13 . The kit of  claim 10 , wherein the free radical stabilizer is butylated hydroxyl anisole and said anionic vapor phase stabilizer is sulfur dioxide. 
     
     
         14 . The kit of  claim 10 , wherein the sterilized cyanoacrylate adhesive composition further comprises therapeutic-loaded nanoparticles. 
     
     
         15 . A method of making the sterilized cyanoacrylate adhesive composition of  claim 2 , comprising
 mixing 99% or more by weight, based on the weight of the adhesive composition, of 2-octyl cyanoacrylate with a free radical stabilizer, an anionic vapor phase stabilizer, and 100 to 1000 parts per million, based on the weight of the adhesive composition, of a 18-crown-6 crown ether to form a cyanoacrylate adhesive composition, and   sterilizing the composition by irradiating the composition,   wherein the sterilized cyanoacrylate adhesive composition does not cure upon sterilization.   
     
     
         16 . The method of  claim 15 , wherein the adhesive remains fluid following storage for twelve days at 80° C. 
     
     
         17 . The method of  claim 15 , further comprising treating the composition with a particulate agent selected from the group consisting of vinyl pyrrolidone polymers and co-polymers. 
     
     
         18 . The method of  claim 15 , wherein the anionic vapor phase stabilizer is present in the composition at a concentration of less than 20 parts per million. 
     
     
         19 . The method of  claim 15 , wherein the free radical stabilizer is butylated hydroxyl anisole and said anionic vapor phase stabilizer is sulfur dioxide. 
     
     
         20 . The method of  claim 15 , further comprising mixing therapeutic-loaded nanoparticles together with the cyanoacrylate adhesive composition. 
     
     
         21 . The method of  claim 15 , wherein said sterilizing comprises irradiating the composition with gamma irradiation, electron beam irradiation, microwave irradiation, or ultraviolet radiation. 
     
     
         22 . A method of sealing tissue, comprising
 applying the sterilized cyanoacrylate adhesive composition of  claim 2  to a patent's tissue, and   allowing the sterilized composition to cure.