Bioabsorbable composition and coatings including same

• US 20060188545A1
• Filed: 01/23/2004
• Published: 08/24/2006
• Est. Priority Date: 01/24/2003
• Status: Active Grant

• Current Assignee: Covidien LP (Medtronic Plc)
• Original Assignee: Tyco Healthcare Group LP (Medtronic Plc)
• Inventors: Hadba, Ahmad R
• Granted Patent: US 8,007,822 B2
• Time in Patent Office: Days
• US Class Current: 424/426
• CPC Class Codes: A61B 18/1445 at the distal end of a shaft, e.g. forceps or scissors at the end of a rigid rod
• CPC Class Codes: A61B 2018/0063 Sealing
• CPC Class Codes: A61B 2018/00702 Power or energy
• CPC Class Codes: A61B 2018/00791 Temperature
• CPC Class Codes: A61B 2018/00875 Resistance or impedance
• CPC Class Codes: A61L 17/12 Homopolymers or copolymers of glycolic acid or lactic acid
• CPC Class Codes: A61L 17/145 Coating
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• CPC Class Codes: C08K 5/098 Metal salts of carboxylic acids
• CPC Class Codes: C08L 2666/18 Polyesters or polycarbonates according to C08L67/00 - C08L69/00; Derivatives thereof
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence

Abstract

Bioabsorbable compositions of A) blends of bioabsorbable homopolymers and/or copolymers containing glycolide and lactide and B) salts of fatty acids and/or fatty acid esters are described. Processes for making the compositions and surgical articles made totally or in part therefrom, including suture coatings, are also described.

Claims

1. A bioabsorbable composition comprising:

1) a blend of component A and B; and

2) a member selected from the group consisting of a salt of a fatty acid and a salt of a fatty acid ester;

wherein component A comprises the reaction product of a bioabsorbable copolymer obtained by polymerizing a major amount of epsilon-caprolactone and a minor amount of at least one other copolymerizable monomer and component B comprises a member selected from the group consisting of bioabsorbable polymer and bioabsorbable copolymer.

2. The composition of claim 1 wherein the fatty acid salts are selected from the group consisting of the magnesium, barium, aluminum, and zinc salts of C₆ and higher fatty acids and mixtures thereof.

3. The composition of claim 1 wherein the fatty acid salts are selected from the group consisting of the magnesium, barium, aluminum, and zinc salts of about C₁₂ to about C₂₂ fatty acids and mixtures.

4. The composition of claim 1 wherein the fatty acid salts are selected from the group consisting of the calicum of about C₁₂ to about C₂₂ fatty acids and mixtures thereof.

5. The composition of claim 1 wherein the fatty acid salts are calcium salts of stearic, palmitic and oleic acids.

6. The composition of claim 1 wherein the fatty acid salt is calcium stearate.

7. The composition of claim 1 wherein the salt of the fatty acid ester is lactylate ester of a C₁₀ or greater fatty acid.

8. The composition of claim 1 wherein the salt of the fatty acid ester is selected from the group consisting of magnesium stearoyl lactylate, aluminum stearoyl lactylate, barium stearoyl lactylate zinc stearoyl lactylate, calcium palmityl lactylate, magnesium palmityl lactylate, aluminum palmityl lactylate barium palmityl lactylate, or zinc palmityl lactylate, calcium olelyl lactylate, magnesium olelyl lactylate, aluminum olelyl lactylate, barium olelyl lactylate, and zinc olelyl lactylate.

9. The composition of claim 1 wherein the salt of the fatty acid ester is calcium stearoyl lactylate.

10. The composition of claim 1 wherein component A comprises the reaction product of a bioabsorbable copolymer obtained by polymerizing a major amount of epsilon-caprolactone and a minor amount of at least one other copolymerizable monomer. in the presence of a polyhydric alcohol initiator.

11. The composition of claim 10 wherein the polyhydric alcohol initiator is selected from the group consisting of glycerol, trimethylolpropane, 1,2,4-butanetriol 1,2,6-hexanetriol triethanolamine, triisopropanolamine, erythritol, threitol pentaerythritol, ribitol arabinitol xylitol N,N,N′

,N′

-tetraois(2-hydroxy-ethyl)ethylenediamine, N,N,N′

,N′

-tetraois(2-hydroxypropyl)ethylenediamine, dipentaerythritol, allitol, dulcitol, glucitol, altritol, iditol, sorbitol, mannitol and inositol.

12. The composition of claim 1 wherein the other copolymerizable monomer is selected from the group consisting of glycolide, lactide, p-dioxanone and trimethylene carbonate.

13. The composition of of claim 1 wherein the copolymer of component A comprises from about 70 to about 98 weight percent epsilon-caprolactone-derived units, the balance of the copolymer being derived from the other copolymerizable monomer(s).

14. The composition of of claim 1 wherein the copolymer of component A comprises from about 80 to about 95 weight percent epsilon-caprolactone derived units, the balance of the copolymer being derived from the other copolymerizable monomer(s).

15. The composition of of claim 2 wherein the polyhydric alcohol is employed in an amount of from about 0.5 to about 5 weight percent of the total monomer mixture.

16. The composition of of claim 1 wherein the polyhydric alcohol initiator is employed in an amount of from about 0.1 to about 2 weight percent of the total monomer mixture.

17. The composition of claim 1 wherein the bioabsorbable polymer of component B is selected from the group consisting of homopolymer of glycolide, homopolymer of lactide.

18. The composition of claim 1 wherein the bioabsorbable copolymer of component B is a copolymer of glycolide and lactide.

19. The composition of claim 1 wherein the bioabsorbable copolymer of component B is a copolymer of lactide and a member selected from the group consisiting of poly (p-dioxanone), poly(alkylene oxalate), copolymers of vinyl acetates, water soluble or dispersible cellulose derivatives, hydroxymethyl cellulose and carboxymethyl cellulose;

natural gums, ethylene oxide polymers, polyacrylamide, collagen, gelatin, polyamino acids, polyvinyl alcohol, polyvinyl pyrrolidone, absorbable conjugated unsaturated triglycerides, and mixtures thereof.

20. The composition of claim 1 wherein the bioabsorbable copolymer of component B is a copolymer of lactide and a member selected from the group consisiting of poly (p-dioxanone), poly(alkylene oxalate), copolymers of vinyl acetates, water soluble or dispersible cellulose derivatives, hydroxymethyl cellulose and carboxymethyl cellulose;

natural gums, ethylene oxide polymers, polyacrylamide, collagen, gelatin, polyamino acids, polyvinyl alcohol, polyvinyl pyrrolidone, absorbable conjugated unsaturated triglycerides, and mixtures thereof.

21. The composition of claim 18 wherein the copolymer of glycolide and lactide comprises from about 90 to about 65 mole percent lactide and from about 10 to about 35 mole percent glycolide.

22. The composition of claim 1 wherein the weight ratio of the member selected from the group consisting of salt of a fatty acid salt and salt of a fatty acid ester to blend of component A and component B is from about 4:

1 to about 1;

4.

23. The composition of claim 1 wherein the weight ratio of the member selected from the group consisting of salt of a fatty acid salt and salt of a fatty acid ester to blend of component A and component B is from about 1:

1.

24. The composition of claim 1 wherein the blend comprises about 10 to about 90 weight percent of component A and 90 to about 10 weight percent of component B.

25. A medical device fabricated in whole or in part from the composition of claim 1.

26. A surgical suture coated with a coating composition comprising the composition of claim 1.

27. The surgical suture of claim 26 which is a bioabsorbable braided suture.

28. The suture of claim 26 wherein the coating composition is applied to a suture at a level of about 0.3% to about 15% weight percent of the entire coated suture.

29. The suture of claim 26 wherein the coating composition is applied to a suture at a level of about 0.5% to about 8% weight percent of the entire coated suture.

30. The composition of claim 1 further comprising one or more medico-surgically useful substances.

31. The composition of claim 30 comprising at least one member selected from the group consisting of antimicrobial agents, growth promoting agents, antiseptics, anesthetics and anti-inflammatory agents.

32. The composition of claim 31 wherein the antimicrobial agent comprises a member selected from the group consisting of glycopeptides, β

-lactams, quinolones, aminoglycosides, antibiotics heavy metals, heavy metal salts, heavy metal derivatives, biguanides, biguanide salts, biguanide derivatives, phenol, bisphenols, phenol salts, bisphenols salts, phenol derivatives bisphenol derivatives, iodine, iodosphers quatenary ammonium compounds, and combinations thereof.

33. The composition of claim 32 wherein the antibiotic is selected from the group consisting of gentamychins, cephalosporins, penecillins, quinolones, tetracyclines, erythromycins, extended-spectrum macrolides, aminoglycosides, sulfonamides, chloramaphenicol, clindamycin, vancomycin, spectinomycin, carbapenems, monobactams, streptogramin, fosfomycin, tromethamines, teicoplanins, fusidic acid, novobiocin, minocycline, rifampin, polymyxin and combinations thereof.

34. The composition of claim 32 wherein the biguanide is selected from the group consisting of chlorhexidine and alexidine and the phenol and bisphenol is selected from the group consisting of triclosan and hexachlorophene.

35. The composition of claim 24 wherein the blend comprises about 40 to about 60 weight percent of component A and about 60 to 40 weight percent of component B.

36. The composition of claim 24 wherein the blend comprises about 50 weight percent of component A and about 50 weight percent of component B.