Stabilized monomer adhesive compositions

Abstract

A method of sterilizing a polymerizable monomeric adhesive composition includes: providing a polymerizable monomeric adhesive composition in a container, the polymerizable monomeric adhesive composition including a polymerizable 1,1 -disubstituted ethylene monomer and at least one stabilizer; holding the composition in the container for a pre-determined amount of time, which is sufficient to inhibit or eliminate polymerization of the monomer during or immediately after sterilization, before sterilizing the composition; and sterilizing the polymerizable monomeric adhesive composition inside the container.

What is claimed is:  
     
         1 . A method of sterilizing a polymerizable monomeric adhesive composition, comprising: 
 providing a polymerizable monomeric adhesive composition in a container, said polymerizable monomeric adhesive composition comprising a polymerizable 1,1-disubstituted ethylene monomer and at least one stabilizer;    holding said composition in said container for a pre-determined amount of time, which is sufficient to inhibit or eliminate polymerization of the monomer during or immediately after sterilization, before sterilizing the composition; and    sterilizing said polymerizable monomeric adhesive composition inside said container.    
     
     
         2 . The method of  claim 1 , further comprising sealing said polymerizable monomeric adhesive composition inside said container.  
     
     
         3 . The method of  claim 2 , wherein said sealing step is conducted prior to said holding step.  
     
     
         4 . The method of  claim 1 , wherein said providing comprises dispensing said polymerizable monomeric adhesive composition into said container.  
     
     
         5 . The method of  claim 1 , wherein said container is made of glass.  
     
     
         6 . The method of  claim 1 , wherein said pre-determined amount of time is such that said composition immediately after said sterilization has a viscosity level no more than 200% higher than a viscosity level of said composition prior to said sterilization.  
     
     
         7 . The method of  claim 1 , wherein said pre-determined amount of time is such that said composition immediately after said sterilization has a viscosity level no more than 50% higher than a viscosity level of said composition prior to said sterilization.  
     
     
         8 . The method of  claim 1 , wherein said pre-determined amount of time is such that said composition immediately after said sterilization has a viscosity level no more than 20% higher than a viscosity level of said composition prior to said sterilization.  
     
     
         9 . The method of  claim 1 , wherein said pre-determined amount of time is such that said composition immediately after said sterilization has a viscosity level no more than 15% higher than a viscosity level of said composition prior to said sterilization.  
     
     
         10 . The method of  claim 1 , wherein said pre-determined amount of time is at least about 22 hours.  
     
     
         11 . The method of  claim 1 , wherein said pre-determined amount of time is at least one day.  
     
     
         12 . The method of  claim 1 , wherein said pre-determined amount of time is at least two days.  
     
     
         13 . The method of  claim 1 , wherein said pre-determined amount of time is about two days.  
     
     
         14 . The method of  claim 1 , wherein said monomer is at least one member selected from the group consisting of n-butyl cyanoacrylate, 2-octyl cyanoacrylate, ethyl cyanoacrylate, methyl cyanoacrylate, ethoxyethyl cyanoacrylate, and methoxyethyl cyanoacrylate.  
     
     
         15 . The method of  claim 1 , wherein said monomer is in a liquid phase and in a vapor phase, and said at least one stabilizer comprises at least one vapor phase anionic stabilizer and at least one liquid phase anionic stabilizer.  
     
     
         16 . The method of  claim 15 , wherein said at least one liquid phase anionic stabilizer is a very strong mineral acid.  
     
     
         17 . The method of  claim 15 , wherein said at least one vapor phase anionic stabilizer is at least one member selected from the group consisting of sulfur dioxide, boron trifluoride, and hydrogen fluoride.  
     
     
         18 . The method of  claim 17 , wherein said at least one vapor phase anionic stabilizer comprises sulfur dioxide.  
     
     
         19 . The method of  claim 18 , wherein said sulfur dioxide is present in said composition in a concentration of 1-200 parts per million.  
     
     
         20 . The method of  claim 18 , wherein said sulfur dioxide is present in said composition in a concentration of 10-20 parts per million.  
     
     
         21 . The method of  claim 17 , wherein said vapor phase anionic stabilizer comprises boron trifluoride.  
     
     
         22 . The method of  claim 15 , wherein said at least one liquid phase anionic stabilizer is at least one member selected from the group consisting of sulfuric acid, perchloric acid, fluorosulfonic acid, and chlorosulfonic acid.  
     
     
         23 . The method of  claim 22 , wherein said at least one liquid phase anionic stabilizer comprises sulfuric acid.  
     
     
         24 . The method of  claim 23 , wherein said sulfuric acid is present in said composition in a concentration of 1-200 parts per million.  
     
     
         25 . The method of  claim 23 , wherein said sulfuric acid is present in said composition in a concentration of 10-40 parts per million.  
     
     
         26 . The method of  claim 23 , wherein said composition further comprises at least one member selected from the group consisting of boron trifluoride and hydrogen fluoride.  
     
     
         27 . The method of  claim 26 , wherein said composition comprises boron trifluoride.  
     
     
         28 . The method of  claim 15 , wherein said at least one vapor phase anionic stabilizer comprises sulfur dioxide and said at least one liquid phase anionic stabilizer comprises sulfuric acid.  
     
     
         29 . The method of  claim 15 , wherein said composition further comprises a secondary anionic agent.  
     
     
         30 . The method of  claim 1 , wherein said holding is conducted at room temperature.  
     
     
         31 . The method of  claim 1 , wherein said sterilizing is by at least one method selected from the group consisting of dry heat sterilization, gamma irradiation, microwave irradiation, and electron beam irradiation.  
     
     
         32 . The method of  claim 31 , wherein said sterilizing is by dry heat.  
     
     
         33 . The method of  claim 31 , wherein said sterilizing is by electron beam irradiation.  
     
     
         34 . A sterilized product made by the process of  claim 1.