IP Library Granted Patent US 8,652,293
Granted Patent B2
US 8,652,293 · App. 13/440,074 · Granted Feb 18, 2014

Hydrophilic biodegradable adhesives

Inventors: Jason Smith (Pittsburgh, PA); Eric Beckman (Aspinwall, PA)
Assignee: Cohera Medical, Inc.
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Quick Facts
Patent No.
US 8,652,293
App. No.
13/440,074
Granted
Feb 18, 2014
Kind
B2
Abstract

A moisture-curable and biodegradable adhesive that includes the reaction product of: (a) an isocyanate component having an average functionality of at least 2; (b) an active hydrogen component having an average functionality greater than 2.1; and (c) an ionic salt component having an average hydroxyl or amino functionality, or combination thereof, of at least 1.

Claims (43)

1. A method of adhering biological tissue comprising applying a tissue adhesive to tissue, wherein the tissue adhesive comprises the reaction product of:

(a) an isocyanate component having an average functionality of at least 2, wherein the isocyanate component is selected from the group consisting of lysine diisocyanate and derivatives thereof, lysine triisocyanate and derivatives thereof, and combinations thereof;

(b) an active hydrogen component having an average functionality greater than 2.1; and

(c) an ionic salt component having an average hydroxyl or amino functionality, or combination thereof, of at least 1

wherein the reaction product is an isocyanate-functional ionic salt that is moisture-curable and biodegradable.

2. A method according to claim 1 wherein the tissue comprises soft tissue.

3. A method according to claim 1 comprising combining the tissue adhesive with an aqueous alkali solution prior to applying the tissue adhesive to the tissue.

4. A method according to claim 1 comprising adhering a polymer mesh or film to tissue with the tissue adhesive.

5. A method according to claim 1 comprising repairing a soft tissue tear by adhering a polymer mesh or film to soft tissue in the vicinity of the tear with the tissue adhesive.

6. A method according to claim 5 wherein the tissue adhesive comprises

(A) the reaction product of:

(a) an isocyanate component having an average functionality of at least 2, wherein the isocyanate component is selected from the group consisting of lysine diisocyanate and derivatives thereof, lysine triisocyanate and derivatives thereof, and combinations thereof;

(b) a hydroxyl-functional component having an average functionality greater than 2.1; and

(c) an ionic salt component having an average hydroxyl or amino functionality, or combination thereof, of at least 1,

wherein the reaction product is an isocyanate-functional salt that is moisture-curable and bio-degradable;

(B) a solvent, non-volatile diluent, or combination thereof; and

(C) a volatile diluent selected from the group consisting of hydrofluoroalkanes, perfluoroalkanes, and combinations thereof.

7. A kit comprising (a) a polymer mesh or film and (b) a tissue adhesive that comprises the reaction product of:

(a) an isocyanate component having an average functionality of at least 2, wherein the isocyanate component is selected from the group consisting of lysine diisocyanate and derivatives thereof, lysine triisocyanate and derivatives thereof, and combinations thereof;

(b) an active hydrogen component having an average functionality greater than 2.1; and

(c) an ionic salt component having an average hydroxyl or amino functionality, or combination thereof, of at least 1,

wherein the reaction product is an isocyanate-functional ionic salt that is moisture-curable and biodegradable.

8. A kit according to claim 7 wherein the tissue adhesive comprises

(A) the reaction product of:

(a) an isocyanate component having an average functionality of at least 2, wherein the isocyanate component is selected from the group consisting of lysine diisocyanate and derivatives thereof, lysine triisocyanate and derivatives thereof, and combinations thereof;

(b) a hydroxyl-functional component having an average functionality greater than 2.1; and

(c) an ionic salt component having an average hydroxyl or amino functionality, or combination thereof, of at least 1,

wherein the reaction product is an isocyanate-functional ionic salt that is moisture-curable and biodegradable;

(B) a solvent, non-volatile diluent, or combination thereof; and

(C) a volatile diluent selected from the group consisting of hydrofluoroalkanes, perfluoroalkanes, and combinations thereof.

9. An article comprising (a) a polymer mesh or film and (b) a tissue adhesive provided on or within the polymer mesh or film, wherein the tissue adhesive comprises the reaction product of:

(a) an isocyanate component having an average functionality of at least 2, wherein the isocyanate component is selected from the group consisting of lysine diisocyanate and derivatives thereof, lysine triisocyanate and derivatives thereof, and combinations thereof;

(b) an active hydrogen component having an average functionality greater than 2.1; and

(c) an ionic salt component having an average hydroxyl or amino functionality, or combination thereof, of at least 1,

wherein the reaction product is an isocyanate-functional ionic salt that is moisture-curable and biodegradable.

10. An article according to claim 9 wherein the tissue adhesive comprises

(A) the reaction product of:

(a) an isocyanate component having an average functionality of at least 2, wherein the isocyanate component is selected from the group consisting of lysine diisocyanate and derivatives thereof, lysine triisocyanate and derivatives thereof, and combinations thereof;

(b) a hydroxyl-functional component having an average functionality greater than 2.1; and

(c) an ionic salt component having an average hydroxyl or amino functionality, or combination thereof, of at least 1,

wherein the reaction product is an isocyanate-functional ionic salt that is moisture-curable and biodegradable;

(B) a solvent, non-volatile diluent, or combination thereof; and

(C) a volatile diluent selected from the group consisting of hydrofluoroalkanes, perfluoroalkanes, and combinations thereof.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2019
From: COHERA MEDICAL, INC.
To: DSI ASSIGNMENTS
Reel/Frame 051318/0730 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2019
From: DSI ASSIGNMENTS, LLC
To: ARTHREX, INC.
Reel/Frame 051318/0757 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Aug 7, 2017
From: COHERA MEDICAL, INC.
To: KKR CHROME INVESTORS L.P.
Reel/Frame 043460/0502 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 5, 2012
From: SMITH, JASON; BECKMAN, ERIC J.
To: COHERA MEDICAL, INC.
Reel/Frame 029407/0001 →
Continuity (3)
Division 12123927 · May 20, 2008
Continuation In Part 11781539 · Jul 23, 2007
Related Publication 20120197293A1 · Aug 2, 2012