CA2299935A1 - Bioabsorbable materials and medical devices made therefrom - Google Patents

Bioabsorbable materials and medical devices made therefrom Download PDF

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Publication number
CA2299935A1
CA2299935A1 CA002299935A CA2299935A CA2299935A1 CA 2299935 A1 CA2299935 A1 CA 2299935A1 CA 002299935 A CA002299935 A CA 002299935A CA 2299935 A CA2299935 A CA 2299935A CA 2299935 A1 CA2299935 A1 CA 2299935A1
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CA
Canada
Prior art keywords
lactide
molar percent
alpha
glycolide
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002299935A
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French (fr)
Other versions
CA2299935C (en
Inventor
Deger C. Tunc
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Howmedica Osteonics Corp
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Stryker Technologies Corp
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Publication of CA2299935A1 publication Critical patent/CA2299935A1/en
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Publication of CA2299935C publication Critical patent/CA2299935C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
    • A61B17/00—Surgical instruments, devices or methods, e.g. tourniquets
    • A61B17/56—Surgical instruments or methods for treatment of bones or joints; Devices specially adapted therefor
    • A61B17/58—Surgical instruments or methods for treatment of bones or joints; Devices specially adapted therefor for osteosynthesis, e.g. bone plates, screws, setting implements or the like
    • A61B17/68—Internal fixation devices, including fasteners and spinal fixators, even if a part thereof projects from the skin
    • A61B17/80—Cortical plates, i.e. bone plates; Instruments for holding or positioning cortical plates, or for compressing bones attached to cortical plates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/04—Macromolecular materials
    • A61L31/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S606/00—Surgery
    • Y10S606/907—Composed of particular material or coated
    • Y10S606/91—Polymer

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  • Health & Medical Sciences (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Surgery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Molecular Biology (AREA)
  • Medical Informatics (AREA)
  • Biomedical Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Vascular Medicine (AREA)
  • Epidemiology (AREA)
  • Materials For Medical Uses (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

A bioabsorbable material such as a terpolymer of poly-(L-lactide/D-lactide/glycolide).
The material may consist of 85 molar percent L-lactide, 5 molar percent D-lactide, and 10 molar percent glycolide. The material may have a heat of fusion of about 15-25 J/G, tensile strength retention at 26 weeks of incubation of at least about 50%, and tensile strength retention at 52 weeks of incubation of at most about 25%. The material may be used in implantable devices such as bone fixation devices.

Claims (33)

1. A material comprising poly-(L-lactide/D-lactide/glycolide).
2. The material of claim 1 comprising at least about 2 molar percent D-lactide.
3. The material of claim 2 comprising at least about 4 molar percent D-lactide.
4. The material of claim 2 comprising about 2 to about 10 molar percent D-lactide.
5. The material of claim 4 comprising about 80-90 molar percent L-lactide, about 2-10 molar percent D-lactide, and about 5-15 molar percent glycolide.
6. The material of claim 5 comprising about 83-87 molar percent L-lactide, about 3-7 molar percent D-lactide, and about 8-12 molar percent glycolide.
7. The material of claim 6 consisting essentially of 85 molar percent L-lactide, 5 molar percent D-lactide, and 10 molar percent glycolide.
8. The material of claim 5 further comprising about 0.1-5 molar percent of a polymer formed from alpha-hydroxy-alpha-ethylbutyric acid; alpha-hydroxy-beta-methylvaleric acid; alpha-hydroxyacetic acid; alpha-hydroxybutyric acid; alpha-hydroxycaproic acid;
alpha-hydroxydecanoic acid; alpha-hydroxyheptanoic acid; alpha-hydroxyisobutyric acid;
alpha-hydroxyisocaproic acid; alpha-hydroxyisovaleric acid; alpha-hydroxymyristic acid;
alpha-hydroxyoctanoic acid; alpha-hydroxystearic acid; alpha-hydroxyvaleric acid;
beta-butyrolactone; beta-propiolactide; gamma-butyrdactone; pivalolactone; or tetramethylglycolide; or combinations thereof.
9. A process of making a material, the process comprising:
a) combining L-lactic acid monomer, glycolic acid monomer and at least about 2 molar percent D-lactic acid monomer to form a mixture; and b) polymerizing substantially all of the mixture.
10. The process of claim 9 wherein the polymerization is preformed in the presence of a catalyst.
11. The process of claim 10 wherein the polymerization is preformed for between 24 and 72 hours.
12. An implantable medical device comprising poly-(L-lactide/D-lactide/glycolide).
13. The medical device of claim 12 wherein the device is selected from the group consisting of a bone plate, bone screw, mesh, suture anchor, tack, pin or intramedullary rod.
14. The medical device of claim 13 consisting essentially of unreinforced poly-(L-lactide/D-lactide/glycolide).
15. The medical device of Claim 14 consisting essentially of reinforced poly-(L-lactide/D-lactide/glycolide).

-14-~
16. A method of using a bioabsorbable bone fixation device, the method comprising:
a) providing a bioabsorbable bone fixation device comprising poly-(L-lactide/D-lactide/glycolide), the device disposed in a first shape in a free state; then b) heating the bone fixation device; and then c) applying force to the device so that the device obtains a second-shape in a free state which is different than the first shape and which approaches the shape of a bone surface to which it will be attached.
17. The method of using of claim 16 wherein the heating is preformed at between about 55°C to about 130°C for between about 2 to about 10 seconds.
18. Polymeric material having a heat of fusion of about 0.4-10 J/G, tensile strength retention at 26 weeks of incubation of at least about 50% and tensile strength retention at 52 weeks at incubation of at most about 25%.
19. The polymeric material of claim 18 wherein the material comprises poly-(L-lactide/D-lactide/glycolide).
20. The polymeric material of claim 19 comprising at least about 2 molar percent D-lactide.
21. The polymeric material of claim 20 comprising about 80-90 molar percent L-lactide, about 2-10 molar percent D-lactide, and about 5-15 molar percent glycolide.
22. Polymeric resin having a heat of fusion of about 15 to about 25 J/G, which upon molding has tensile strength retention at 26 weeks of incubation of at least about 50%
and tensile strength retention at 52 weeks of incubation of at most about 25%.
23. The polymeric material of claim 22 wherein the material comprises poly-(L-lactide/D-lactide/glycolide).
24. The polymeric material of claim 23 comprising at least about 2 molar percent D-lactide.
25. The polymeric material of claim 24 comprising about 80-90 molar percent L-lactide, about 2-10 molar percent D-lactide, and about 5-15 molar percent glycolide.
26. Polymeric material having tensile strength at 0 weeks of incubation of about 65-101 MPa, tensile strength at 26 weeks of incubation of about 50-75 MPa, tensile strength at 44 weeks of incubation of about 0-37 MPa, and tensile strength at 60 weeks of incubation of 0 MPa.
27. The polymeric material of claim 26 comprising poly-(L-lactide/D-lactide/glycolide).
28. The polymeric material of claim 26 having a heat of fusion of about 0.4-10 J/G.
29. The polymeric material of claim 28 having a heat of fusion of about 0.5-5 J/G.
30. The polymeric material of claim 26 formed from a resin having a heat of fusion of about 15-25 J/G.
31. The polymeric material of claim 30 formed from a resin having a heat of fusion of about 18-21 J/G.
32. The polymeric material of claim 26 having tensile strength at 0 weeks of incubation of about 74-92 MPa, tensile strength at 26 weeks of incubation of about 56-69 MPa, and tensile strength at 44 weeks of incubation of about 9-27 MPa.
33. A material comprising poly-(L-lactide/D-lactide/glycolide) made by the process comprising:
(a) combining L-lactic acid monomer, glycolic acid monomer and at least about 2 molar percent D-lactic acid monomer to make a mixture; and (b) polymerizing substantially all of the mixture.
CA2299935A 1999-03-05 2000-03-03 Bioabsorbable materials and medical devices made therefrom Expired - Lifetime CA2299935C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/263,268 US6206883B1 (en) 1999-03-05 1999-03-05 Bioabsorbable materials and medical devices made therefrom
US09/263,268 1999-03-05

Publications (2)

Publication Number Publication Date
CA2299935A1 true CA2299935A1 (en) 2000-09-05
CA2299935C CA2299935C (en) 2010-02-23

Family

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Family Applications (1)

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CA2299935A Expired - Lifetime CA2299935C (en) 1999-03-05 2000-03-03 Bioabsorbable materials and medical devices made therefrom

Country Status (6)

Country Link
US (2) US6206883B1 (en)
EP (1) EP1034806B1 (en)
JP (1) JP2000300660A (en)
AU (1) AU766678B2 (en)
CA (1) CA2299935C (en)
DE (1) DE60011687T2 (en)

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