Bioabsorbable adhesive compounds

• US 20060111537A1
• Filed: 10/23/2003
• Published: 05/25/2006
• Est. Priority Date: 10/28/2002
• Status: Abandoned Application

• Current Assignee: Tyco Healthcare Group LP (Medtronic Plc)
• Original Assignee: Tyco Healthcare Group LP (Medtronic Plc)
• Inventors: Roby, Mark
• Application Number:
  US10/533,041
• Publication Number:
  US 20060111537A1
• Time in Patent Office: Days
• US Class Current: 528/44
• CPC Class Codes: A61L 24/046 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L24/043 takes precedence
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/76 aromatic
• CPC Class Codes: C08G 18/8029 Masked aromatic polyisocyanates
• CPC Class Codes: C08G 2230/00 Compositions for preparing biodegradable polymers
• CPC Class Codes: C08K 5/29 Compounds containing one or more carbon-to-nitrogen double bonds
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C09J 175/06 from polyesters

Abstract

Bioabsorbable adhesive or sealant suitable for use in medical or surgical applications contain three compounds. The first compound is an isocyanate-endcapped absorbable oligumer. The second compound is a trifunctional compound that is also diisocyanate terminated, or end-capped. The third compound is an aromatic diisocyanate.

Claims

1. A composition comprising:

a bioabsorbable oligomeric compound that is end-capped with an aromatic diisocyanate;

a trifunctional compound that is end-capped with an aromatic diisocyanate; and

an aromatic diisocyanate.

2. A composition as in claim 1 wherein the bioabsorbable oligomeric compound is a compound having the structure:

[A]_n−

X

wherein A is a bioabsorbable group, n is from 1 to about 6 and X is a residue from a multifunctional initiator.

3. A composition as in claim 2 wherein the bioabsorbable group is a group derived from a monomer selected from the group consisting of glycolic acid, glycolide, lactic acid, lactide, 1,4-dioxane-2-one, 1,3-dioxane-2-one and ε

-caprolactone.

4. A composition as in claim 2 wherein X is a residue from a multifunctional initiator selected from the group consisting of diols, aromatic and alkyl triols, polyols, alcohol amines, dicarboxylic acids and aromatic dicarboxylic acids.

5. A composition as in claim 2 wherein X is a residue from a multifunctional initiator selected from the group consisting of ethylene glycol, diethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, 1,2-decanediol, 1,2-dodecanediol, 1,2-hexadecanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 2-methyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 2-ethyl-3-butyl-1,3-propanediol, 2-ethyl-1,6-hexanediol, glycerol, 1,1,1-trimethylolpropane, neopentyl glycol, pentaerythritol, triethanolamine, 1- aminopropanols, 2-aminopropanols, 2- aminobutanols, 4-aminobutanols, succinic acid, glutaric acid, adipic acid, suberic acid, sebacic acid, dodecanedioic acid, 2-ethyl-2-methylsuccinic acid, phthalic acid, isophthalic acid, and terephthalic acid.

6. A composition as in claim 1 wherein the bioabsorbable oligomer is end-capped with an aromatic diisocyanate selected from the group consisting of 1,4-diisocyanatobenzene, 1,1′

-methylenebis[4-isocyanatobenzene], 2,4-diisocyanato-1-methylbenzene, 1,3-diisocyanato-2-methylbenzene, 1,5-diisocyanatonaphthalene, 1,1′

-(1-methylethylidene)bis[4-isocyanatobenzene) and 1,3- and 1,4-bis(1-isocyanato-1-methylethyl)benzene.

7. A composition as in claim 1 wherein the trifunctional compound is selected from the group consisting of glycerol, 1,1,1-trimethylolpropane, neopentyl glycol, pentaerythritol, triethanolamine, 1- aminopropanols, 2-aminopropanols, 2- aminobutanols, 4-aminobutanols.

8. A composition as in claim 1 wherein the trifunctional compound is end-capped with an aromatic diisocyanate selected from the group consisting of 1,4-diisocyanatobenzene, 1,1′

-methylenebis[4-isocyanatobenzene], 2,4-diisocyanato-1-methylbenzene, 1,3-diisocyanato-2-methylbenzene, 1,5-diisocyanatonaphthalene, 1,1′

-(1-methylethylidene)bis[4-isocyanatobenzene) and 1,3- and 1,4-bis(1-isocyanato-1-methylethyl)benzene.

9. A composition as in claim 1 wherein the aromatic diisocyanate is selected from the group consisting of 1,4-diisocyanatobenzene, 1,1′

-methylenebis[4-isocyanatobenzene], 2,4-diisocyanato-1-methylbenzene, 1,3-diisocyanato-2-methylbenzene, 1,5-diisocyanatonaphthalene, 1,1′

-(1-methylethylidene)bis[4-isocyanatobenzene) and 1,3- and 1,4-bis(1-isocyanato-1-methylethyl)benzene.

13. A composition as in claim 1 wherein the bioabsorbable oligomeric compound that is end-capped with an aromatic diisocyanate is present in an amount from about 50 to about 95 percent by weight of the composition;

the trifunctional compound that is end-capped with an aromatic diisocyanate is present in an amount from about 5 to about 40 percent by weight of the composition; and

the aromatic diisocyanate is present in an amount from about 1 to about 10 percent by weight of the composition.

14. A composition as in claim 1 wherein the bioabsorbable oligomeric compound that is end-capped with an aromatic diisocyanate is present in an amount from about 70 to about 90 percent by weight of the composition;

the trifunctional compound that is end-capped with an aromatic diisocyanate is present in an amount from about 8 to about 25 percent by weight of the composition; and

the aromatic diisocyanate is present in an amount from about 2 to about 5 percent by weight of the composition.

15. A method of adhering first and second tissue surfaces, the method comprising approximating the first and second tissue surfaces;

and applying to the approximated tissue surfaces a composition of claim 1.

16. A method of adhering a surgical device to tissue, the method comprising:

applying to the surgical device a composition of claim 1;

and contacting the surgical device with tissue.

17. A method of sealing a defect in tissue, the method comprising identifying a tissue site containing a defect;

and applying a composition of claim 1 to the site of the defect.

18. A method for reducing leakage of bodily fluids or air comprising applying to a tissue defect a composition in accordance with claim 1 and crosslinking the composition.

21. A method as in claim 17 wherein crosslinking comprises contacting the composition with a compound selected from the group consisting of water, diethylene glycol and polyethylene glycol.

22. A method as in claim 17 wherein crosslinking includes the use of a catalyst.

23. A method as in claim 17 wherein crosslinking is conducted at temperatures from about 20°

C. to about 40°

C. for a time from about thirty seconds to about one hour.

24. A method as in claim 17 wherein crosslinking is conducted at least partially prior to application to tissue.

10. (canceled)

11. (canceled)

12. (canceled)

19. A composition comprising:

a bioabsorbable oligomeric compound that is end-capped with an aromatic diisocyanate, wherein the bioabsorbable oligomeric compound has the structure;

[A]_n−

X

wherein A is a bioabsorbable group derived from a monomer selected from the group consisting of glycolic acid, glycolide, lactic acid, lactide, 1,4-dioxane-2-one, 1,3-dioxane-2-one and ε

-caprolactone, n is from about 1 to about 6 and X is a residue from a multifunctional initiator selected from the group consisting of ethylene glycol, diethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, 1,2-decanediol, 1,2-dodecanediol, 1,2-hexadecanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 2-methyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 2-ethyl-3-butyl-1,3-propanediol, 2-ethyl-1,6-hexanediol, glycerol, 1,1,1-trimethylolpropane, neopentyl glycol, pentaerythritol, triethanolamine, 1- aminopropanols, 2-aminopropanols, 2- aminobutanols, 4-aminobutanols, succinic acid, glutaric acid, adipic acid, suberic acid, sebacic acid, dodecanedioic acid, 2-ethyl-2-methylsuccinic acid, phthalic acid, isophthalic acid, and terephthalic acid;

a trifunctional compound that is end-capped with an aromatic diisocyanate, wherein the trifunctional compound is selected from the group consisting of glycerol, 1,1,1-trimethylolpropane, neopentyl glycol, pentaerythritol, triethanolamine, 1-aminopropanols, 2-aminopropanols, 2-aminobutanols, 4-aminobutanols; and

an aromatic diisocyanate selected from the group consisting of 1,4-diisocyanatobenzene, 1,1′

-methylenebis[4-isocyanatobenzene], 2,4-diisocyanato-1-methylbenzene, 1,3-diisocyanato-2-methylbenzene, 1,5-diisocyanatonaphthalene, 1,1′

-(1-methylethylidene)bis[4-isocyanatobenzene) and 1,3- and 1,4-bis(1-isocyanato-1-methylethyl)benzene.

20. A method of comprising:

applying to tissue a composition compsrising a bioabsorbable oligomeric compound that is end-capped with an aromatic diisocyanate;

a trifunctional compound that is end-capped with an aromatic diisocyanate; and

an aromatic diisocyanate; and

crosslinking the composition.