Bioabsorbable composition and coatings of a fatty acid salt, epsilon-caprolactone, a monomer, and homopolymers or copolymers

• US 8,329,205 B2
• Filed: 07/21/2011
• Issued: 12/11/2012
• Est. Priority Date: 01/24/2003
• Status: Expired due to Fees

• Current Assignee: Covidien LP (Medtronic Plc)
• Original Assignee: Covidien LP (Medtronic Plc)
• Inventors: Hadba, Ahmad R.
• Primary Examiner(s): AZPURU, CARLOS A
• Application Number:
  US13/187,574
• Publication Number:
  US 20110287083A1
• Time in Patent Office: 509 Days
• Field of Search: None
• 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;

2) a salt of a fatty acid; and

one or more medico-surgically useful substances;

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 homopolymers of glycolide, homopolymers of lactide, and copolymers of lactide and a member selected from the group consisting 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.

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 thereof.

4. The composition of claim 1, wherein the fatty acid salts are selected from the group consisting of the calcium 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 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.

8. The composition of claim 7, 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.

9. The composition of claim 7, wherein the polyhydric alcohol is employed in an amount from about 0.5 to about 5 weight percent of the total monomer mixture.

10. The composition of claim 7, 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.

11. The composition 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).

12. The composition 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).

13. The composition of claim 1, comprising at least one member selected from the group consisting of antimicrobial agents, growth promoting agents, antiseptics, anesthetics and anti-inflammatory agents.

14. The composition of claim 13 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, bisphenol salts, phenol derivatives bisphenol derivatives, iodine, iodosphers quaternary ammonium compounds, and combinations thereof.

15. The composition of claim 14, 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, teicoplanin, fusidic acid, novobiocin, minocycline, rifampin, polymyxin and combinations thereof.

16. The composition of claim 14, 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.

17. A medical device fabricated in whole or in part from a composition comprising:

1) a blend of component A and B;

2) a salt of a fatty acid; and

one or more medico-surgically useful substances;

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.

18. A surgical suture coated with a coating composition comprisinga blend of component A and B;

2) a salt of a fatty acid; and

one or more medico-surgically useful substances;

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.

19. The surgical suture of claim 18, which is a bioabsorbable braided suture.

20. The suture of claim 18, 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.

21. The suture of claim 18, 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.