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CA2092646A1 - Bioabsorbable blends of a bioabsorbable copolymer and a poly(oxyalkylene) - Google Patents

Bioabsorbable blends of a bioabsorbable copolymer and a poly(oxyalkylene)

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Publication number
CA2092646A1
CA2092646A1 CA 2092646 CA2092646A CA2092646A1 CA 2092646 A1 CA2092646 A1 CA 2092646A1 CA 2092646 CA2092646 CA 2092646 CA 2092646 A CA2092646 A CA 2092646A CA 2092646 A1 CA2092646 A1 CA 2092646A1
Authority
CA
Grant status
Application
Patent type
Prior art keywords
poly
copolymer
percent
blend
oxyalkylene
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.)
Abandoned
Application number
CA 2092646
Other languages
French (fr)
Inventor
Ross R. Muth
Nagabhushanam Totakura
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.)
United States Surgical Corp
Original Assignee
United States Surgical Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/04Polyesters derived from hydroxycarboxylic acids, e.g. lactones
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14Macromolecular materials
    • A61L27/26Mixtures of macromolecular compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28Materials for coating prostheses
    • A61L27/34Macromolecular materials
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L33/00Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
    • A61L33/0005Use of materials characterised by their function or physical properties
    • A61L33/0011Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate
    • A61L33/0029Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate using an intermediate layer of polymer
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00Compositions of polycarbonates; Compositions of derivatives of polycarbonates
    • C08L69/005Polyester-carbonates
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02Polyalkylene oxides
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D169/00Coating compositions based on polycarbonates; Coating compositions based on derivatives of polycarbonates
    • C09D169/005Polyester-carbonates

Abstract

ABSTRACT
Bioabsorbable compositions useful for coating medical devices include a blend or physical mixture of a poly(oxyalkylene), such as polyethylene oxide, and a bioabsorbable copolymer having soft segments, such as glycolide-trimethylene carbonate copolymer.

Description

2~92~46 203-396 (1?69) nIOA13SORI~BI,E l~LENDS Ol; A ~IOAl~SORBA13Ll:
COPOLYMER AND A rOLY(O~YYALl~YLEl~E) I;IE:LD Oli TIIE INVr,NT~ON
This invention relates generally to novel bioabsorbable compositions.
More particularly, this invention relates to new bioabsorbable polymer blends useful for coating medical devices.

~J~CKGROIJN~ O~ TIII~ INYI;,NTION
Bioabsorbable coa~ings are applied to a wide range of medical devices for a variety of reasons. The natllre of the medical device used as the substrate for the coating wilt normally determine which particular characteristics are desired in the coating. For example, implantable porous prostheses for use as bone or other hard tissue replacements are usually formecl from polymeric beads or parlic]es having a biologically compatible, hydropllilic coating. The hydrophilic coating on the particles facilitates infllsioll of body fluids into the pores of the implant, ~hereby faci1itating the ingrowth of tissue into the pores of the implant. Such prostheses are described in U.S. Patent Nos. 4,728,570; 4,535,485; 4,547,327; and 4,536,158.
As another example, synthetic vascular grafts made from tubes of fabric rnay be manufactured from yarns coated with a hydrophilic coating. In addition, a surface of the fabric may be coated with an absorbable coating to temporarily render the olllerwise porous fabric impervious to blood and~or other body fluids. It is desirable that ~he fluids-occlllcling coa~ing exhibit sufrlcient elasticity to accommodate the alternate elongation ancl contraction which llle tubular fabric prothesis llndergoes when implanted in the body. Such tubular fabric protheses are described in U.S. Palelll No. 4,990,158.

2092~6 In certain applications, a medical device may advantageously include a hydrophobic coating. ~Iydropl~obic coatings provi~le desirable handling characteristics, allowing easy and accurate positioning of the device, better holding of knots, and decreased slipping in the gloved hands of surgeons. Additional1y, medicat devices with hydrophobic coatings may provide improved tissue retaining properties, for example, where it is desired to hold tissue together.
Copolymers of glycolide and trimethylene carbonate (also referred to as 1,3-dioxan-2-one) have been used to fabricate bioabsorbable medical devices or surgical articles. See for example, U.S. Patent Nos. 4,243,775; ~,300,565;
4,429,030; 4,633,873; and 4,719,917. ~dditionally, glycolide-trimethylene carbonate (GTMC) polymers have been applied to sutures and other surgical articles as a bioabsorbable coating. Sce U.S. Patent Nos. 4,705,820 and 4,7~8,979. GTMC
polymers have also been formed into filaments and braided witll non-absorbable components (see U.S. Patent No. 4,792,336) and used to coat or encapsulate a woven mesh or other textile structllres formed by filaments of non~absorbable polymers (see Europem Patent ~pplication No. 0334046).
U.S. Patent No. 4,452,973 describes poly(glycolic acid)/poly(oxyalkylene) AB~ triblock copolymers useflll as absorbable sutures.

SUMMAR~ OF T~TE INVENTTON
It has now been found tllat blends of poly(oxyalkylene) with a bioabsorbable copolymer having soft segments are llseful as bioabsorbable compositions, sucll as, for example bioabsorbable coatings for medical drvices.
Tllese blends provide coatings wllicl- have good elastic, durability and llydropllilic and/or hydrophobic properties as required ror a particular end use. The soft segments of the copolymer may be forrned by incorporating into tlle copolymer a monomer ; . -, , .
.
-- . - -2~9~

selected from the group consisting of trimethylene carbonate, dioxanone, caprolactone, a]ky]ene oxalates, hytiroxybutyrates, esteramides, hydroxyva]erates, urcthanes, hexamethy]ene carbonate and mixtllres thereof. The blend optiona]]y 5 includes a medico-surgica]ly usefill substance, such as, for examp]e, an antithrombogenic substance.

DESCRIPrlON Oli' PRr,lir,RRr,D r,MnODIMr,NTS
The compositions of the present invention comprise polymer blends containing or physical mixtures Or: (a) a bioabsorbable copolymer having soft segments; and (b) poly(oxyalkylene).
Bioabsorbable copolymers suitable for preparing the blends of this invention contain onc or more comonomer which provide soft segments. ~or example, soft segments may be incorporated into polymers of glycolide, lactide or glycolide lactide copolymers by incorporatillg trimethylene carbonate as a comonomer during polymerization. Other comonomers suitable for generating soft segments include dioxanone, caprolactone, alkylene oxalates, hydroxyblltyrates, esteramides, 20 hydroxyvalerates, llrethanes, hexamethylene carbonate and mixtures thereof.
Trimethylene carbonate, dioxanone and caprolactone are the preferred comonomers.These comonomers may be present in an amount up to 75 mole percent, and preferably between abollt 65 mole percent.
The bioabsorbable copolymer used in the present invention may be formed by copolymerizing one or morc Or Ihe aforementioned sof~ segment comonomers with one or more monomers known to produce a bioabsorbable polymer, such as, for example, glycolide or lactide. ~referred bioabsorbable copolymer include copolymers of glycolide and trimethylene carbonate.

., ;~ ~ '-: ', 2~926~

Glycolide-trimethylene carbonate copolymers employed in particularly usefl11 ernbodiments of the present invenlion may contain up to about 50 mole percent glycolide and llp to abollt 75 mole percent trimethylene carbonate. A preferred 5 copolymer is glycolide/trimethylene carbonate (GTMC) copolymer containing about 35 mole percent glycolide and about 65 mole percent trimethylene carbonate.
Polyoxyalkylenes usefill in this invention incl~lde those which are hydrophilic in nature, such as, for example, polyethylene oxide, poly(oxyethylene- !
l O oxypropylene) copolymers and block copolymers of polyoxyethylene and polyoxypropylene commercially available under the tradename Pluronic.
Hydrophobic polyethers may also be used in the present blends. Sllitable hydrophobic polyethers include polypropylene oxide, polypentylene oxide and poly-1,4-butane diol.
Polyelhylene oxide tPEO) polymers suitable for llse in this invention are commercially available in a wide variety of molecular weights. Preferred polyethylene oxide polymers are those having a molecular weight from about 400 to about 20,000. Most preferred is a polyetllylene oxide with a molecular weight of8000. Generally, as the amolmt of polyethylene oxide in the blend is increased, the 20 hydrophylicity of the blend will increase. The polymer blends may include poly(oxyalkylene) in an amount up to about 50 percent based on the total weight of the blend. Preferably, the blend will contain between abollt 10 and 20 percent polyalkylene oxide based on the total weight of the blend.
The compositions of the present invention may be formulated to possess a desired set of characteristics depending on the application in which tl~e compositions are to be used. I~or example, the hydrophobic or hydropllilic natllre of the composition may be adjusted by the choice of polyalkylene oxide or mixture of polyalkylene oxides. ~ balancc of hydropllilic and hydropllobic characteristics are achievable by thc compositions Or tl~e present inventiom ~s another examplc, the rate .

.

2~2~

at which the composition bioabsorbs may be adjllsted by varying the amounts of glycolide and trimethylene carbonate in the copolymer.
Otller components may be included in the compositions of this 5 invention sucll that tlle coating compositions are employed as a carrier for one or more medico-surgically usefill subs~ances, e.g., those which accelerate or otherwise beneficially modify the healing process ~vhen applied to a wound or surgical siie. In general, any biologically active material which is sol~lble in and otherwise compatible 10 with the selected coating composition can be incorporated therein in therapeutically useful annollnts. I~or example, a therape~ltic agent may be chosen for its antimicrobial properties, capability for promoting wound repair and/or tissue growth or for specific indica~ions sucll as thrombolysis. Antimicrobial agents such as broad spectmm antibio~ics (gentamycin sulpllate, erytllromycin or derivatized glycopeptides) which are slowly released in~o the ~issue can be applied in tl-is manner to aid in combating clinical and sub-clinical infections in a surgical or trauma wound site. To promote wound repair and/or tiss~le growth, one or several growtll promoting factors can be added to the coating, e.g., fibroblast growth ractor, bone growth factor, epidermal 20 growth factor, plalelet derived growtll factor, macrophage derived growth factor, alveolar derived growth factor, monocy~e derived growth factor, magainin, and soforth. Some therapeutic indications are: gTycerol with tissue or kidney plasminogen activator to cause tllrombolysis, s~lperoxide dismlltase to scavenge tissue damaging 25 free radicals, tumor necrosis factor for cancer therapy or colony stimulating factor and interferon, interlellkin-2 or otl1er Iymphokine to enhance the immune system.
Other examples Or materia]s whicll may be addetl to the blends of tllis invention inclllde antitllroml)ogellic agents (sllch as heparin, hirlldin and prostaglandins), 30 pharmaco10gically iac~ive agents, anti-coagulants, osteogenic factors, anti-filngals, imm~mosuppressive agcnts, anti-inrlamlllatory agents, preservatives, saccharides, .: ~

2~92~ ~

diagnostic agents, antihistamines, hormones, enzymes, peptides ancltor steroids. The amount of each additional component added ~ill depend on the particlllar nature of the component and the purpose for aclding the component. Typically, however, thes amount of each optiona1 component will be below about 10% by weight of the toka weight of the blend.
The phrase "total weight Or the blend" is intende(l to include ~he weight of GTMC and poly(oxyalkylene) and any additional ingredients included in the blend, 10 but is intended to exclude the weight of the solvent, if any, employed in mixing or applying the blend.
The preparation and application of the polymer blends of the present invention may be accomplished by any suitable melhod which provides a substantially homogenous mixture of the two principal polymer components (i.e., GTMC and poly(oxyalkylene)). For example, tlle bioabsorbable copolymer and poly(oxyalkylene) may be melt blended. Preferably, the components of the blends are dissolved in asolvent and mixed to providc a substantially homogenolls solution. Tlle solution is applied to a substrate such as a medical device, and the solvent is removed, such as 20 for example, by evaporation.
More particul~rly, in forming the solution it is preferred to first dissolve the GTMC polymer in just enougll solvent to dissolve the polymer with stirring. Then the poly(oxyalkylene) is slowly added with continlled stirring. If 2~; necessary, adclitional amounts of solvent may be added to efrectuate complete dissolving of the poly(oxyalkylene).
The compositions of this invention form absorbable rllms having good durability, elastic and hydrophilic or hydropl1obic properties. They may be used for 30 surface coating and/or encapsul;lting and may act to r~ll voids or interstices in medical dcvices, sucll as, ror example, vascnlar grart ma~crials or beacls used to form .

- . , ...
. . . .. .

2 ~ 9 2 6 ~ ~

orthopedic or dental implants. The coating composi~ions may be applied to absorbable or non-absorbable substrates.

Corolvmcr rlcparation A copolymer of glycolide and trimetl)ylene carbonate was prepared by melt phase ring opening copolymerization of 28.42 grams (35 mole percent) glycolide O and 46.41 grams (65 mole percent) trimelhylene carbonate in the presence of stannous octoate (1.9 cc of .2 gms Or stannous octoate ~lissolved in 25 cc of ether) in an appropriate reaction vessel at 1600C for 12 hollrs. After polymerization the vessel was allowed to cool to room temperature. The polymer was then removed from the vessel, dried in vacuum and kept dry until used.

I'olvmcr l~lcnd Prc~ar:ltio 22.5 grams of dried poly (glycolide-co-trimethylene carbonate) was placed into a round bottom flask and dissolved in about 200 ml of methylene chloride.
20 Polyethylene oxide (2.5 gms; molecular weigllt 8000) was slowly adlled to this solution wllile stirring. After complete addition of polyethylene oxide, stirring of the mixture was conlinued for 16 hours. Arter tl-orougll mixing, the solution mixture was poured into a dish and lhe excess solvent was evaporated. The thick film formed was 5 dried well under vacullm (24 hours at room temperature) and stored dry. The resulting material contained 90% GTMC copolymer and 10% PEO.

Coatin~ Onto Yn.sclllar Grnrt Tul)cs A polymcr blend was prepared as described above containing 20 percent polyethylene oxide based on tl-c total weight of lhe blend. A 5% sollltion of . ~ . . .
- .- - , -. :

2~.~2~

tlle blend in methylene chloridc was applied to a Iengtll of a vascular graft tube having a diameter of 2-3 mm by dipping the tube into the solution and evaporating off the solvent. The vascular graft tube was woven from filaments of both absorbable5 and non-absorbable materials; namely, filaments of poly(glycolide/lactide) andfilaments of Hytrel 5556 (an elastomer commercially available from E. I. duPont de Nemours ~ Co., Delaware). Irt vitro tesling suggests that the blend of this Example would begin to absorb in about 2-3 hollrs after implantation into a mammalian body.
It is not intended to limit the present invention to the specific embodiments described above. It is recognized that changes may be made in the coating compositions specifically described herein without departing from the scope and teaching of the instant invention, and it is intended to encompass all other embodiments, alternatives an(l modifilcalions consistent with the invention.

. , : ~ , : , ; ~ . :

Claims (30)

1. A bioabsorbable composition comprising a mixture of:
a bioabsorbable copolymer having soft segments; and a poly(oxyalkylene).
2. A composition according to claim 1 wherein said soft segments are provided in said copolymer by one or more comonomers selected from the groupconsisting of trimethlylene carbonate, dioxanone, coprolactones, alky1ene oxylates, hydroxybutyrates, esteramides, hydroxyvalerates, urethanes, hexamethylene carbonate, and mixtures thereof.
3. A composition according to claim 1 wherein said soft segment comonomer is present in said copolymer in an amount of up to about 75 mole %.
4. A composition according to claim 1 wherein said soft segment comonomer is present in said copolymer in an amount of about 65%.
5. A composition according to claim 1 wherein said poly(oxyalkylene) is present in the mixture in an amount less than about 30 percent based on the weight of the total mixture.
6. A composition according to claim 2 wherein said copolymer comprises one or more monomers selected from the group consisting of glycolide and lactide.
7. A composition according to claim 1 further comprising an effective amount of a medico-surgically useful substance.
8. A composition according to claim 1 wherein said medico-surgically useful substance is an antithrombogenic agent.
9. A composition according to claim 8 wherein said antithrombogenic agent is selected from the group consisting of heparin, hirudin and prostaglandins.
10. A bioabsorbable composition comprising a mixture of:
a copolymer of glycolide and trimethylene carbonate; and a poly(oxyalkylene).
11. A composition according to claim 10 wherein said poly(oxyalkylene) is present in the mixture in an amount less than about 30 percent based on the weight of the total mixtures.
12. A composition according to claim 10 wherein the copolymer comprises:
glycolide in an amount up to about 50 mole percent; and trimethylene carbonate in an amount up to about 75 mole percent.
13. A composition according to claim 10 wherein said copolymer comprises about 35 mole percent glycolide and about 65 percent mole trimethylenecarbonate.
14. A composition according to claim 10 wherein said poly(oxyalkylene) is present in an amount from about 10 percent to about 20 percent based on the weight of the mixture.
15. A composition according to claim 10 wherein said poly(oxyalkylene) is selected from the group consisting of polyethylene oxide, polypropylene oxide, poly(oxyethylene-oxypropylene) copolymers, polypentylene oxide, poly-1,4-butane diol and block copolymers of polyoxyethylene and polyoxypropylene.
16. A composition as in claim 10 wherein said poly(oxyalkylene) is polyethylene oxide.
17. A composition as in claim 16 wherein said polyethylene oxide is present in an amount less than 30 percent based on the weight of the mixture.
18. A method of coating a medical device comprising applying to the device a blend of a poly(oxyalkylene) and a bioabsorbable copolymer having soft segments.
19. A method as in claim 18 wherein said soft segments are provided in said copolymer by polymerizing one or more comonomers selected from the group consisting of trimethylene carbonate, dioxanone, caprolactone, alkylene oxalates, hydroxybutyrates, esteramides, hydroxyvalerates, urethanes, hexamethylene carbonate and mixtures thereof with one or more monomers selected from the groupconsisting of glycolide and lactide.
20. A method according to claim 18 wherein said poly(oxyalkylene) is present in the blend in an amount less than about 30 percent based on the total weight of the blend.
21. A method according to claim 18 wherein poly(oxyalkylene) is present in the blend in an amount from about 10 to about 20 percent based on thetotal weight of the blend.
22. A method according to claim 18 wherein the copolymer comprises glycolide in an amount up to about 50 mole percent and trimethylene carbonate in an amount up to about 75 mole percent.
23. A method according to claim 18 wherein the copolymer comprises about 35 mole percent glycolide and about 55 mole percent trimethylenecarbonate.
24. A method according to claim 18 wherein the step of applying said blend comprises:
preparing a solution by dissolving a poly(oxyalkylene) and a said copolymer in a solvent;
applying said solution to the medical device; and removing said solvent.
25. A method according to claim 18 wherein said poly(oxyalkylene) is selected from the group consisting of polyethylene oxide, polypropylene oxide;
poly(oxyethylene-oxypropylene), copolymers, polypentylene oxide, poly-1,4-butanediol and block copolymers of polyoxyethylene and polyoxypropylene.
26. A method as in claim 18 wherein said blend further comprises an effective amount of a medico-surgically useful substance.
27. A method as in claim 26 wherein said medico-surgically useful substance is an antithrombogenic agent.
28. A method of coating a medical device comprising applying a blend of a poly(oxyalkylene) and a copolymer of glycolide and trimethylene carbonate to at least a portion of the medical device.
29. A method according to claim 28 wherein said poly(oxyalkylene) is present in the blend in an amount less than about 30 percent based on the total weight of the blend.
30. A method according to claim 28 wherein poly(oxyalkylene) is present in the blend in an amount from about 10 to about 20 percent based on thetotal weight of the blend.
CA 2092646 1992-03-25 1993-03-12 Bioabsorbable blends of a bioabsorbable copolymer and a poly(oxyalkylene) Abandoned CA2092646A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US85761692 true 1992-03-25 1992-03-25
US07/857,616 1992-03-25

Publications (1)

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Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0652017B2 (en) * 1993-10-07 2004-01-07 Axel Dr. Stemberger Coating for biomaterial
US5788979A (en) * 1994-07-22 1998-08-04 Inflow Dynamics Inc. Biodegradable coating with inhibitory properties for application to biocompatible materials
US5607686A (en) * 1994-11-22 1997-03-04 United States Surgical Corporation Polymeric composition
DE19514104C2 (en) * 1995-04-13 1997-05-28 Behringwerke Ag Coating for can be introduced into the bloodstream or into the tissue of the human body biomaterial
US5641502A (en) * 1995-06-07 1997-06-24 United States Surgical Corporation Biodegradable moldable surgical material
DE19718430A1 (en) * 1997-04-30 1999-01-14 Stemberger Axel Dr Anti=infective treatment of bio=material, e.g. prosthesis
US9616150B2 (en) 1999-10-29 2017-04-11 Children's Hospital Los Angeles Bone hemostasis method and materials
WO2004071451A3 (en) 2003-02-12 2005-09-22 Ceremed Inc Random alkylene oxide copolymers for medical and surgical utilities
CA2526541C (en) 2004-12-01 2013-09-03 Tyco Healthcare Group Lp Novel biomaterial drug delivery and surface modification compositions

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Publication number Priority date Publication date Assignee Title
US4047533A (en) * 1976-09-20 1977-09-13 American Cyanamid Company Absorbable surgical sutures coated with polyoxyethylene-polyoxypropylene copolymer lubricant
US4923470A (en) * 1985-04-25 1990-05-08 American Cyanamid Company Prosthetic tubular article made with four chemically distinct fibers
US4649920A (en) * 1986-01-30 1987-03-17 Pfizer Hospital Products Group, Inc. Coated suture
DE3779838D1 (en) * 1986-09-05 1992-07-23 American Cyanamid Co Coating for surgical filaments.
US5080665A (en) * 1990-07-06 1992-01-14 American Cyanamid Company Deformable, absorbable surgical device
CA2067451A1 (en) * 1991-05-24 1993-10-29 Gregory B. Kharas Polylactide blends

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