Absorbable cyanoacrylate compositions

• US 20080003196A1
• Filed: 06/30/2006
• Published: 01/03/2008
• Est. Priority Date: 06/30/2006
• Status: Abandoned Application

• Current Assignee: Ethicon Incorporated (Johnson & Johnson)
• Original Assignee: Ethicon Incorporated (Johnson & Johnson)
• Inventors: Quintero, Julian A., Badejo, Ibraheem T., Warren, Teresa, Vander Klok, Melanie A., Jonn, Jerry Y.
• Application Number:
  US11/479,424
• Publication Number:
  US 20080003196A1
• Time in Patent Office: Days
• US Class Current: 424/78.08
• CPC Class Codes: A61L 24/06 obtained by reactions only involving carbon-to-carbon unsaturated bonds A61L24/043, A61L24/046 take precedence
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: C09J 4/00 Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16

Abstract

An adhesive composition is provided including one or more polymerizable cyanoacrylate monomers and boron trifluoride as a stabilizer or complexing agent. The adhesive composition may also include or be used with a decomplexing agent, particularly one or more quaternary ammonium fluoride salts or one or more quaternary ammonium ether salts. A polymerization initiator or accelerator may also be used. The viscosity of the adhesive composition may be controlled by addition of a thickening agent which may be a polymer or copolymer catalyzed by a boron trifluoride complex or compound. Methods for the application of the adhesive compositions to living tissue are also provided.

Claims

1. An adhesive composition comprising:

one or more polymerizable cyanoacrylate monomers,

a complexing agent for the one or more polymerizable cyanoacrylate monomers comprising boron trifluoride, and

a decomplexing agent comprising at least one quaternary ammonium fluoride salt, at least one quaternary ammonium ether salt, or mixtures thereof.

2. The adhesive composition of claim 1 wherein the quaternary ammonium fluoride salt comprises a compound according to formula A:

3. The adhesive composition of claim 1 wherein the quaternary ammonium ether salt comprises a compound according to formula B:

4. The adhesive composition of claim 1 further comprising a polymerization initiator comprising a quaternary ammonium chloride salt.

5. The adhesive composition of claim 1 wherein the one or more polymerizable cyanoacrylate monomers are 2-octyl cyanoacrylate and butyl lactoyl cyanoacrylate.

6. The adhesive composition of claim 1 further comprising a thickening agent comprising an absorbable polyester catalyzed by a boron trifluoride catalyst.

7. An adhesive composition comprising:

a first monomer species comprising an alkyl ester cyanoacrylate having the formula

8. The adhesive composition of claim 7 wherein the second monomer species is an alkyl α

-cyanoacrylate.

9. The adhesive composition of claim 8 wherein the alkyl α

-cyanoacrylate is octyl 2-cyanoacrylate.

10. The adhesive composition of claim 7 further comprising a thickening agent comprising an absorbable polyester catalyzed by a boron trifluoride catalyst.

11. The adhesive composition of claim 7 wherein the quaternary ammonium fluoride salt comprises a compound according to formula A:

12. The adhesive composition of claim 7 wherein the quaternary ammonium ether salt comprises a compound according to formula B:

13. The adhesive composition of claim 7 further comprising a plasticizer.

14. An adhesive composition comprising:

one or more polymerizable cyanoacrylate monomers,

at least one anionic stabilizer,

at least one free radical stabilizer, and

at least one thickening agent comprising an absorbable polyester catalyzed by a boron trifluoride catalyst.

15. A method of treating living tissue, comprising:

applying to living tissue a biocompatible adhesive composition comprising one or more polymerizable cyanoacrylate monomers and a complexing agent for the one or more polymerizable cyanoacrylate monomers comprising boron trifluoride, wherein the biocompatible adhesive composition is applied in conjunction with a decomplexing agent comprising at least one quaternary ammonium fluoride salt, at least one quaternary ammonium ether salt, or mixtures thereof.

16. The method of claim 15 wherein the biocompatible adhesive composition further comprises a polymerization initiator comprising a quaternary ammonium chloride salt.

17. The method of claim 15 wherein the living tissue is internal living tissue.

18. The method of claim 15 wherein the one or more polymerizable cyanoacrylate monomers are 2-octyl cyanoacrylate and butyl lactoyl cyanoacrylate.

19. The method of claim 15 wherein the biocompatible adhesive composition is sterilized by dry heat sterilization prior to being applied to living tissue.

20. The method of claim 15 wherein the biocompatible adhesive composition further comprises a thickening agent comprising an absorbable polyester catalyzed by a boron trifluoride catalyst.