Absorbable adhesive compositions

• US 20020037310A1
• Filed: 08/02/2001
• Published: 03/28/2002
• Est. Priority Date: 08/02/2000
• Status: Abandoned Application

• Current Assignee: Ethicon Incorporated (Johnson & Johnson)
• Original Assignee: Closure Medical Corporation (Johnson & Johnson)
• Inventors: Moseley, Jon P., Bobo, John, Burns, Dennis D., Quintero, Julian, Jonn, Jerry Y.
• Application Number:
  US09/919,877
• Publication Number:
  US 20020037310A1
• Time in Patent Office: Days
• US Class Current: 424/448
• 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: C08F 222/328 Alpha-cyano-acrylic acid with more than one oxygen in the ester moiety
• CPC Class Codes: C08L 35/04 Homopolymers or copolymers of nitriles C08L35/06, C08L35/08 take precedence
• 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

A method of treating living tissue includes applying to living tissue a biocompatible adhesive composition, where the adhesive composition contains at least one alkyl ester cyanoacrylate monomer and a polymerization initiator or accelerator, wherein the polymerization initiator or accelerator is a quaternary amine, or where the adhesive composition contains a mixture of two monomer species having different absorption rates.

Claims

1. A biocompatible adhesive composition, comprising:

a first monomer species; and

a second monomer species different from said first monomer species,

wherein at least said first monomer species is absorbable, and

an absorption rate of said first monomer species is different from an absorption rate of said second monomer species.

2. The biocompatible adhesive composition of claim 1, wherein said first monomer species comprises an alkyl ester cyanoacrylate.

3. The biocompatible adhesive composition of claim 2, wherein said alkyl ester cyanoacrylate has the formula

4. The biocompatible adhesive composition of claim 2, wherein said alkyl ester cyanoacrylate is selected from the group consisting of butyl lactoyl cyanoacrylate, butyl glycoloyl cyanoacrylate, isopropyl glycoloyl cyanoacrylate, ethyl lactoyl cyanoacrylate, and ethyl glycoloyl cyanoacrylate.

5. The biocompatible adhesive composition of claim 1, wherein said first monomer species comprises an alkyl ether cyanoacrylate.

6. The biocompatible adhesive composition of claim 5, wherein said alkyl ether cyanoacrylate has the formula

7. The biocompatible adhesive composition of claim 6, wherein said alkyl ether cyanoacrylate is selected from the group consisting of isopropoxy ethyl cyanoacrylate and methoxy butyl cyanoacrylate.

8. The biocompatible adhesive composition of claim 1, wherein said second monomer species comprises a cyanoacrylate other than an alkyl ester cyanoacrylate and an alkyl ether cyanoacrylate.

9. The biocompatible adhesive composition of claim 8, wherein said second monomer species is an alkyl α

-cyanoacrylate, having an alkyl group of from about 2 to about 12 carbon atoms.

10. The biocompatible adhesive composition of claim 8, wherein said second monomer species is selected from the group consisting of octyl α

-cyanoacrylate, hexyl α

-cyanoacrylate, butyl α

-cyanoacrylate and ethyl α

-cyanoacrylate.

11. The biocompatible adhesive composition of claim 1, wherein a weight ratio of said first monomer species to said second monomer species is from about 25:

75 to about 75;

25.

12. The biocompatible adhesive composition of claim 1, wherein said first monomer species comprises an alkyl ester cyanoacrylate and said second monomer species comprises an alkyl α

-cyanoacrylate.

13. The biocompatible adhesive composition of claim 1, wherein said first monomer species comprises butyl lactoyl cyanoacrylate and said second monomer species comprises octyl α

-cyanoacrylate.

14. The biocompatible adhesive composition of claim 1, wherein said composition further comprises at least one additive selected from the group consisting of anionic stabilizing agents, free radical stabilizing agents, colorants, and plasticizers.

15. The biocompatible adhesive composition of claim 1, wherein said composition comprises:

a monomer blend comprising from about 25 to about 40 parts by weight butyl lactoyl cyanoacrylate and from about 60 to about 75 parts by weight octyl cyanoacrylate (OCA);

at least one anionic stabilizer; and

at least one radical stabilizer.

16. The biocompatible adhesive composition of claim 15, wherein said at least one anionic stabilizer comprises about 25 to about 100 ppm of sulfuric acid and from about 1 to about 50 ppm sulfur dioxide, and said at least one radical stabilizer comprises from about 100 to about 2000 ppm hydroquinone, from about 10 to about 200 ppm p-methoxyphenol, and from about 100 to about 10,000 ppm butylated hydroxyanisole.

17. The biocompatible adhesive composition of claim 1, wherein said first and second monomer species have different absorption rates, such that an absorption rate of a faster absorbing monomer species is at least 10% faster than an absorption rate of a slower absorbing monomer species.

19. The method of claim 18, wherein two or more polymerization initiators or accelerators are applied to said living tissue.

46. A method of treating living tissue, comprising:

applying to internal living tissue in a living organism the biocompatible adhesive composition of claim 1.

18. A method of treating living tissue, comprising:

applying to living tissue a biocompatible adhesive composition comprising at least one alkyl ester cyanoacrylate monomer and a polymerization initiator or accelerator, wherein said polymerization initiator or accelerator is a purified benzalkonium chloride.

20. A method of treating living tissue, comprising:

applying to living tissue a biocompatible adhesive composition comprising;

at least one alkyl ester cyanoacrylate monomer;

a second monomer species having an absorption rate different from an absorption rate of said at least one alkyl ester cyanoacrylate monomer; and

a polymerization initiator or accelerator, wherein said polymerization initiator or accelerator is a quaternary amine.

21. The method of claim 20, wherein two or more polymerization initiators or accelerators are applied to said living tissue.

22. The method of claim 20, wherein said second monomer species comprises a cyanoacrylate other than an alkyl ester cyanoacrylate and an alkyl ether cyanoacrylate.

23. The method of claim 22, wherein said second monomer species is an alkyl α

-cyanoacrylate, having an alkyl group of from about 2 to about 12 carbon atoms.

24. The method of claim 22, wherein said second monomer species is selected from the group consisting of octyl α

-cyanoacrylate, hexyl α

-cyanoacrylate, butyl α

-cyanoacrylate and ethyl α

-cyanoacrylate.

25. The method of claim 20, wherein a weight ratio of said at least one alkyl ester cyanoacrylate monomer to said second monomer species is from about 25:

75 to about 75;

25.

26. The method of claim 20, wherein said at least one alkyl ester cyanoacrylate monomer comprises butyl lactoyl cyanoacrylate and said second monomer species comprises octyl α

-cyanoacrylate.

27. The method of claim 20, wherein said adhesive composition further comprises at least one additive selected from the group consisting of anionic stabilizing agents, free radical stabilizing agents, colorants, and plasticizers.

29. The kit of claim 28, wherein said first monomer species comprises an alkyl ester cyanoacrylate.

30. The kit of claim 29, wherein said alkyl ester cyanoacrylate has the formula

31. The kit of claim 29, wherein said alkyl ester cyanoacrylate is selected from the group consisting of butyl lactoyl cyanoacrylate, butyl glycoloyl cyanoacrylate, isopropyl glycoloyl cyanoacrylate, ethyl lactoyl cyanoacrylate, and ethyl glycoloyl cyanoacrylate.

32. The kit of claim 28, wherein said second monomer species comprises a cyanoacrylate other than an alkyl ester cyanoacrylate and an alkyl ether cyanoacrylate.

33. The kit of claim 32, wherein said second monomer species is an alkyl α

-cyanoacrylate, having an alkyl group of from about 2 to about 12 carbon atoms.

34. The kit of claim 32, wherein said second monomer species is selected from the group consisting of octyl α

-cyanoacrylate, hexyl α

-cyanoacrylate, butyl α

-cyanoacrylate and ethyl α

-cyanoacrylate.

35. The kit of claim 28, wherein a weight ratio of said first monomer species to said second monomer species is from about 25:

75 to about 75;

25.

36. The kit of claim 28, wherein said first monomer species comprises an alkyl ester cyanoacrylate and said second monomer species comprises an alkyl α

-cyanoacrylate.

37. The kit of claim 28, wherein said first monomer species comprises butyl lactoyl cyanoacrylate and said second monomer species comprises octyl α

-cyanoacrylate.

38. The kit of claim 28, wherein said composition further comprises at least one additive selected from the group consisting of anionic stabilizing agents, free radical stabilizing agents, colorants, and plasticizers.

39. The kit of claim 28, wherein said polymerization initiator or accelerator is a quaternary amine.

40. The kit of claim 28, wherein said polymerization initiator or accelerator is selected from the group consisting of domiphen bromide and benzyldimethylhexadecylammonium chloride.

41. The kit of claim 28, wherein said first and second monomer species are contained in a same container.

42. The kit of claim 28, wherein said first and second monomer species are contained in different containers in said kit.

43. The kit of claim 28, wherein said polymerization initiator or accelerator is a polymerization initiator or accelerator for said first monomer species, and said kit further comprises a second polymerization initiator or accelerator that is a polymerization initiator or accelerator for said second monomer species.

44. The kit of claim 28, further comprising one or more additives mixed with at least one of said first and said second monomer species.

45. The kit of claim 28, further comprising one or more additives that is separated from said first and said second monomer species.

47. The method of claim 46, wherein said first monomer species comprises an alkyl ester cyanoacrylate.

48. The method of claim 47, wherein said alkyl ester cyanoacrylate has the formula

49. The method of claim 47, wherein said alkyl ester cyanoacrylate is selected from the group consisting of butyl lactoyl cyanoacrylate, butyl glycoloyl cyanoacrylate, isopropyl glycoloyl cyanoacrylate, ethyl lactoyl cyanoacrylate, and ethyl glycoloyl cyanoacrylate.

50. The method of claim 46, wherein said second monomer species comprises a cyanoacrylate other than an alkyl ester cyanoacrylate and an alkyl ether cyanoacrylate.

51. The method of claim 50, wherein said second monomer species is an alkyl α

-cyanoacrylate, having an alkyl group of from about 2 to about 12 carbon atoms.

52. The method of claim 50, wherein said second monomer species is selected from the group consisting of octyl α

-cyanoacrylate, hexyl α

-cyanoacrylate, butyl α

-cyanoacrylate and ethyl α

-cyanoacrylate.

53. The method of claim 46, wherein a weight ratio of said first monomer species to said second monomer species is from about 25:

75 to about 75;

25.

54. The method of claim 46, wherein said first monomer species comprises an alkyl ester cyanoacrylate and said second monomer species comprises an alkyl α

-cyanoacrylate.

55. The method of claim 46, wherein said first monomer species comprises butyl lactoyl cyanoacrylate and said second monomer species comprises octyl α

-cyanoacrylate.

56. The method of claim 46, wherein said composition further comprises at least one additive selected from the group consisting of anionic stabilizing agents, free radical stabilizing agents, colorants, and plasticizers.

57. The method of claim 46, wherein said polymerization initiator or accelerator is a quaternary amine.

58. The method of claim 46, wherein said polymerization initiator or accelerator is selected from the group consisting of domiphen bromide and benzyldimethylhexadecylammonium chloride.

60. The composition of claim 59, further comprising a second different polymerization initiator or accelerator.

61. The composition of claim 60, wherein said second monomer species comprises a cyanoacrylate other than an alkyl ester cyanoacrylate and an alkyl ether cyanoacrylate.

62. The composition of claim 61, wherein said second monomer species is an alkyl α

-cyanoacrylate, having an alkyl group of from about 2 to about 12 carbon atoms.

63. The composition of claim 61, wherein said second monomer species is selected from the group consisting of octyl α

-cyanoacrylate, hexyl α

-cyanoacrylate, butyl α

-cyanoacrylate and ethyl α

-cyanoacrylate.

64. The composition of claim 60, wherein a weight ratio of said at least one alkyl ester cyanoacrylate monomer to said second monomer species is from about 25:

75 to about 75;

25.

65. The composition of claim 60, wherein said at least one alkyl ester cyanoacrylate monomer comprises butyl lactoyl cyanoacrylate and said second monomer species comprises octyl α

-cyanoacrylate.

66. The composition of claim 60, wherein said adhesive composition further comprises at least one additive selected from the group consisting of anionic stabilizing agents, free radical stabilizing agents, colorants, and plasticizers.

67. A polymerized film formed by curing the composition of claim 59.

28. A kit comprising a saleable package comprising:

a first monomer species;

a second monomer species different from said first monomer species; and

a polymerization initiator or accelerator for at least one of said first and second monomer species,

wherein at least said first monomer species is absorbable, and

an absorption rate of said first monomer species is different from an absorption rate of said second monomer species.

59. A biocompatible adhesive composition, comprising:

at least one alkyl ester cyanoacrylate monomer;

a second monomer species having an absorption rate different from an absorption rate of said at least one alkyl ester cyanoacrylate monomer; and

a polymerization initiator or accelerator, wherein said polymerization initiator or accelerator is a quaternary amine.

68. A polymerized film formed from the polymerization of a first monomer species and a second monomer species different from said first monomer species, wherein at least said first monomer species is absorbable and an absorption rate of said first monomer species is different from an absorption rate of said second monomer species.