US3883901A - Method of replacing or repairing the body with bioresorbable surgical articles - Google Patents

Method of replacing or repairing the body with bioresorbable surgical articles Download PDF

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Publication number
US3883901A
US3883901A US419450A US41945073A US3883901A US 3883901 A US3883901 A US 3883901A US 419450 A US419450 A US 419450A US 41945073 A US41945073 A US 41945073A US 3883901 A US3883901 A US 3883901A
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United States
Prior art keywords
filament
surgical article
bioresorbable
polyester
surgical
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Expired - Lifetime
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US419450A
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English (en)
Inventor
Jean Coquard
Pierre Sedivy
Jean Verrier
Michel Ruaud
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Rhone Poulenc SA
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Rhone Poulenc SA
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • 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
    • A61L17/00—Materials for surgical sutures or for ligaturing blood vessels ; Materials for prostheses or catheters
    • A61L17/06—At least partially resorbable materials
    • A61L17/10—At least partially resorbable materials containing macromolecular materials
    • A61L17/105—Polyesters not covered by A61L17/12
    • 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
    • A61L17/00—Materials for surgical sutures or for ligaturing blood vessels ; Materials for prostheses or catheters
    • A61L17/14—Post-treatment to improve physical properties
    • A61L17/145—Coating
    • 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
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14—Macromolecular materials
    • A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds

Definitions

  • ABSTRACT Implantable surgical articles which are at least partially bioresorbable and which consist at least partially of a polyester of succinic acid possessing a plurality of units of the general formula:
  • R represents a linear or branched alkylene radical containing 2 to 6 carbon atoms. They are particularly suitable as sutures.
  • the present invention relates to surgical articles which are biologically partially or completely resorbable after implantation in living human or animal tissues.
  • the elements for sutures and for ligatures intended for closing wounds and for repairing blood vessels, nerves and tendons are examples of surgical articles which are implanted temporarily. These elements are generally filaments, but they can also be in other forms, for example as clips or tapes.
  • the most commonly used bioresorbable material for making suture or ligature filaments is catgut prepared from the collegen of mammals; the sub-muccous layer of the small intestine of sheep is most frequently employed. Catgut possesses numerous disadvantages, such as difficulty in obtaining it, the unfavourable reactions which it causes with living tissues and the lack of uniformity of its mechanical properties. Consequently, ways have been sought of replacing it by bioresorbable synthetic materials which can easily be converted into continuous filaments by extrusion techniques, and which possess readily reproducible mechanical properties.
  • a surgical article which can be used in human or animal surgery, which is completely or partially bioresorbable and which consists wholly or partially of a bioresorbable material consisting of a polyester of succinic acid possessing a plurality of units of the general formula:
  • R represents a linear or branched alkylene radical containing 2 to 6 carbon atoms. More specifically, R can be an ethylene, methylethylene, 1,2- dimethylethylene, trimethylene, 2-methyltrimethylene, 2,Z-dimethyl-trimethylene, l-methyltrimethylene, tetramethylene, pentamethylene or hexamethylene radical.
  • polyesters of formula (I) denoted hereafter by the general term polysuccinate
  • polysuccinate is unexpected because it is known that polyesters such as polyethylene glycol terephthalate are not resorbed by human or animal tissues (see U.S. Pat. No. 3,463,158). It has been found that, in addition to their bioresorbable character, the polysuccinates are particularly well tolerated by the tissues in which they are implanted; thus no inflammatory reaction has been observed after a long-lasting implantation of polyethylene glycol succinate filaments in rats.
  • polysuccinates possess excellent mechanical properties (notably tensile strength, tensile strength at knots and dimensional stability) and are insensitive to moisture, which make them particularly suitable for the manufacture of surgical articles and especially elements for sutures.
  • Polysuccinate filaments are easy to handle and do not necessitate the use of special storage devices.
  • Polyglycol succinates have been known for a very long time (see, for example, U.S. Pat. No. 2,071,250; and V. V. KORSHAK and S. V. VINOGRADOVA, Polyesters, edited by PERGAMON PRESS Ltd., 1965, pages 31 to 46). They can be prepared by the usual polycondensation processes such as those described by V. V. KORSHAK and S. V. VINO- GRADOVA, loc. cit., or in HOUBEN WEYL, Methoden der Organische Chemie Makromolekulare Stoffe, volume 14/2, pages 1 to 29.
  • esterification or transesterification catalysts such as sulphuric or p-toluenesulphonic acids, or metal salts or oxides such as calcium oxide, strontium oxide, zinc oxide, aluminium oxide, bismuth oxide, iron oxide, titanium oxide, lead oxide, antimony oxide, cobalt oxide, calcium chloride, zinc acetate and zinc borates.
  • glycols which can be used to prepare the polyesters used in the present invention there may be mentioned ethylene glycol, propylene glycol, propane-1,3- diol, 2-methyl-propanel ,3-diol, 2,2-dimethylpropane-1,3-diol, butane-1,4-diol, butane-1,3-diol, butane-2,3-diol, pentane-1,5-diol and hexane-1,6-diol.
  • These various glycols can be used separately or as a mixture with one another.
  • Use can thus be made of mixtures containing 1 to 99 mol of ethylene glycol and 99 to 1 mol of one or more other glycols such as 2-methylpropane-1,3-diol and 2,2-dimethylpropane-1,3-diol.
  • the molecular weight of the polysuccinates used for the production of surgical articles according to the present invention can vary within very wide limits but it should generally be sufficiently high to render them suitable for the formation of films and fibres. Generally it should be sufficiently high for the polymer to be converted into filaments and films which can be orientated.
  • the upper limit is not critical, subject to the condition that the product can be processed by the usual moulding or shaping techniques.
  • Polysuccinates can be used for the production of extremely diverse surgical articles, such as those described in Handbook of Biomedical Plastics, H. LEE and K. NEVILLE, 1971, Pasadena Technology Press. They are particularly suitable for the production of elements for surgical sutures and ligatures, especially in the form of twisted or non-twisted filaments, tapes, bristles, tents or spun fibres. They can also be used in the form of single filaments, twisted filaments, stranded filaments, gathered filaments, texturized filaments or lapped filaments; these various terms are used in accordance with the definition which is given of them in French Standard Specification NF G -005. These various elements for sutures can consist wholly or partially of the bioresorbable polysuccinates.
  • a filament of the polysuccinate or of a filament comprising a core of a non-resorbable synthetic material such as polyethylene glycol terephthalate, polyamide or polypropylene, and an outer coating of polysuccinates.
  • a composite element consisting of a yarn of natural material, e.g., linen or silk, or synthetic material covered with a polysuccinate, or of a yarn of variable structure comprising bioresorbable filaments and nonresorbable filaments.
  • knitted fabrics comprising resorbable yarns and optionally non-resorbable yarns or nonresorbable yarns covered with a layer of polysuccinate; non-woven fabrics prepared from non-bioresorbable fibresand a resorbable binder; and sheets made from non-resorbable materials covered on one or both faces by a polysuccinate.
  • the wholly or partially resorbable knitted and woven fabrics can be used in the form of sheaths intended to facilitate the implantation of diverse prostheses such as that described in French Pat. Nos.
  • the polysuccinates of formula (1) are also very suitable for the production of surgical articles such as tubes of various shapes, for example Y-shaped tubes and T- shaped tubes, bars, plates, rings and screws, intended to be implanted temporarily or permanently.
  • surgical articles such as tubes of various shapes, for example Y-shaped tubes and T- shaped tubes, bars, plates, rings and screws, intended to be implanted temporarily or permanently.
  • Partially or completely bioresorbable tubular prostheses have been described in US Pat. Nos. 2,127,903, 3,272,204, 3,304,557, 3,316,557, and 3,479,670 to which reference should be made for further details.
  • the shaping of the polysuccinates of formula (I) for the production of surgical articles can be carried out by the usual methods.
  • filaments, tapes or sheets can be produced by extrusion of the polymer in the molten state, followed by stretching at a sufficiently high ratio to cause the orientation of the chains of the polymer, and the fixing of the article thus produced.
  • the polysuccinates of formula (I) can contain various adjuvants such as fillers, dyestuffs and plasticizers which are chemically inert and do not bring about any reactions with the living tissues.
  • polyesters of the polyethylene glycol terephthalate or adipate type, or of the polylactide or polyglycolide type can be used alone or mixed with nonbioresorbable materials, as indicated above, or with materials which are more or less resorbable in themselves, for example, respectively, polyesters of the polyethylene glycol terephthalate or adipate type, or of the polylactide or polyglycolide type.
  • the surgical articles according to the invention can be sterilized easily by the techniques usually employed in surgery, for example by radiation treatment.
  • EXAMPLE 1 Preparation of polyethylene glycol succinate 174g. (1 mol) of diethyl succinate, 93 g. (1.5 mols) of ethylene glycol, 0.280 g. of zinc acetate and 0.070 g. of antimony trioxide are introduced, under a stream of nitrogen, into a 300 cm glass flask equipped with a scraping stirrer, a gas inlet tube, a gas outlet tube, a thermometer, a thermostatically controlled metal heating bath and a distillation column provided with a condenser and a receiving container. The contents of the flask are heated to 180C., with stirring, and these conditions are maintained for 1 hour 30 minutes.
  • the temperature of the reaction mixture is then raised to 240C., over the course of 50 minutes and the apparatus is connected to a vacuum pump in order to reduce the pressure in the apparatus to 0.1 mm.Hg over the course of 30 minutes. The whole is maintained under these conditions for 6 hours 30 minutes.
  • the viscous, light brown reaction mixture is dissolved in hot dioxane and then reprecipitated with methanol. A product is obtained which is filtered off and dried at 80C. in a vacuum oven. In this way, 112 g. of polymer are obtained.
  • the polyester thus obtained has a viscosity of 69 cm"*/g., measured at 25C., on a 4 g/l solution in chloroform and a viscosity of 70 cm/g, measured at 25C. in a 2 g/l solution in meta-cresol. lt melts at 104C., and is not decomposed by heating under nitrogen at 300C.
  • a filament of gauge 20 decitex is prepared from this polyester by inelt spinning under 30 bars and stretching the yarn issuing from the spinneret in a ratio of 7 at 55C.
  • This filament possesses the following mechanical properties:
  • Samples of length 1 cm are implanted, with a curved needle, in rats (Caesarean Originated, Barrier Sustained) weighing 250 to 350 g; the implantation is carried out, on the one hand, in the paravertebral muscles, and on the other hand, under the skin of one of the sides of each animal.
  • rats (2 male and 2 female) each received two implants.
  • Two months after the implantation the animals are killed and the muscular implantation region (implant and paravertebral muscular mass) and the subcutaneous implantation region (skin, implant and underlying muscular portion) are removed in each case.
  • the following examinations are carried out on each specimen removed:
  • bioresorbability of the polyethylene glycol succinate produced above is determined by measuring the variation in the reduced viscosity of a sample of polymer taken in the form of flakes and incubated for varying periods of time in an enzyme extract. The test was carried out in the following manner:
  • the homogenized material is then subjected to an ultrasonic treatment (frequency: 20 kHz) for 2 minutes with the same cooling precautions. It is then centrifuged at 6,500 G, at 0 for 20 minutes. The supernatant liquid, filtered through glass wool, forms the enzyme extract; its pH is approximately 4.5.
  • reaction mixture 100 mg. of the polymer to be investigated is incubated at 37C., with agitation (shaking table turning at revolutions/minute), in the following reaction mixture:
  • This reaction mixture is renewed every day; during each renewal, the samples are carefully washed with distilled water.
  • the product to be investigated in the form of flakes, is enclosed in a guaze bag for the incubation.
  • EXAMPLES 2 1. Preparation of polybutane-1,4-diol succinate 1 hour and then to 240C. over the course of 30 minutes, and the pressure is reduced to 0.1 mm.Hg over the course of 40 minutes. After 4 hours 40 minutes under these conditions, the reaction is stopped.
  • Filaments of gauge 21 decitex are prepared from the polymer thus produced by melt spinning under 61 bars and stretching at 85C.
  • the filaments possess the following mechanical properties:
  • 'c l C-0- in which represents a linear or branched alkylene radical containing 2 to 6.carbon atoms having a filmor filament-forming molecular weight.
  • polyester is polyethylene glycol succinate 3.
  • surgical article is in the form of a suture element.
  • the surgical article is in the form of a filament, bristle, single filament, twisted filament, stranded filament, gathered filament, texturized filament of lapped filament, tape, tent or spun fibre.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Vascular Medicine (AREA)
  • Surgery (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Materials For Medical Uses (AREA)
  • Polyesters Or Polycarbonates (AREA)
US419450A 1972-12-01 1973-11-27 Method of replacing or repairing the body with bioresorbable surgical articles Expired - Lifetime US3883901A (en)

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FR7242838A FR2208687B1 (zh) 1972-12-01 1972-12-01

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US (1) US3883901A (zh)
JP (1) JPS5047492A (zh)
BE (1) BE808088A (zh)
BR (1) BR7309394D0 (zh)
CA (1) CA1023493A (zh)
CH (1) CH587659A5 (zh)
DE (1) DE2359865A1 (zh)
DK (1) DK131804C (zh)
FR (1) FR2208687B1 (zh)
GB (1) GB1444817A (zh)
IT (1) IT1048160B (zh)
NL (1) NL7316072A (zh)
NO (1) NO135968C (zh)
SE (1) SE396286B (zh)
ZA (1) ZA739015B (zh)

Cited By (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3960152A (en) * 1974-01-21 1976-06-01 American Cyanamid Company Surgical sutures of unsymmetrically substituted 1,4-dioxane-2,5-diones
US4032993A (en) * 1974-06-28 1977-07-05 Rhone-Poulenc Industries Bioresorbable surgical articles
US4080969A (en) * 1973-11-21 1978-03-28 American Cyanamid Company Suture or ligature carrying on the exposed surface thereof a coating of a polyester resin
US4128612A (en) * 1974-04-19 1978-12-05 American Cyanamid Company Making absorbable surgical felt
US4141087A (en) * 1977-01-19 1979-02-27 Ethicon, Inc. Isomorphic copolyoxalates and sutures thereof
US4186189A (en) * 1977-09-28 1980-01-29 Ethicon, Inc. Absorbable pharmaceutical compositions based on poly(alkylene oxalates)
US4329743A (en) * 1979-04-27 1982-05-18 College Of Medicine And Dentistry Of New Jersey Bio-absorbable composite tissue scaffold
US4343931A (en) * 1979-12-17 1982-08-10 Minnesota Mining And Manufacturing Company Synthetic absorbable surgical devices of poly(esteramides)
US4388926A (en) * 1980-12-22 1983-06-21 Ethicon, Inc. High compliance monofilament surgical sutures comprising poly[alkylene terephthalate-co-(2-alkenyl or alkyl)succinate]
US4396746A (en) * 1981-04-16 1983-08-02 Daicel Chemical Industries, Ltd. Thermoplastic polyester copolymer
US4411027A (en) * 1979-04-27 1983-10-25 University Of Medicine And Dentistry Of New Jersey Bio-absorbable composite tissue scaffold
US4441496A (en) * 1982-02-08 1984-04-10 Ethicon, Inc. Copolymers of p-dioxanone and 2,5-morpholinediones and surgical devices formed therefrom having accelerated absorption characteristics
US4481353A (en) * 1983-10-07 1984-11-06 The Children's Medical Center Corporation Bioresorbable polyesters and polyester composites
EP0144534A2 (en) * 1983-09-20 1985-06-19 Allied Corporation prosthetic devices
US4529792A (en) * 1979-12-17 1985-07-16 Minnesota Mining And Manufacturing Company Process for preparing synthetic absorbable poly(esteramides)
DE3249111C2 (de) * 1981-10-09 1986-02-06 United States Surgical Corp., Norwalk, Conn. Chirurgische kunststoffartige Befestigungseinrichtung zum Festlegen von Körpergewebe
US4603695A (en) * 1983-07-05 1986-08-05 Japan Medical Supply Co., Ltd. Use of molded polymeric material for preventing adhesion of vital tissues
US4652264A (en) * 1985-04-25 1987-03-24 American Cyanamid Company Prosthetic tubular article
US4662884A (en) * 1984-04-25 1987-05-05 University Of Utah Research Foundation Prostheses and methods for promoting nerve regeneration
US4670286A (en) * 1983-09-20 1987-06-02 Allied Corporation Method of forming prosthetic devices
US4738255A (en) * 1986-04-07 1988-04-19 Biotron Labs, Inc. Suture anchor system
US4773416A (en) * 1986-02-07 1988-09-27 Hourahane Donald H Surgery in horses
US4778467A (en) * 1984-04-25 1988-10-18 The University Of Utah Prostheses and methods for promoting nerve regeneration and for inhibiting the formation of neuromas
US4844067A (en) * 1987-02-19 1989-07-04 Japan Medical Supply Co., Ltd. Sucrose fatty acid ester coated suture
US4870966A (en) * 1988-02-01 1989-10-03 American Cyanamid Company Bioabsorbable surgical device for treating nerve defects
US4871365A (en) * 1985-04-25 1989-10-03 American Cyanamid Company Partially absorbable prosthetic tubular article having an external support
US4915893A (en) * 1982-07-16 1990-04-10 Medtronic, Inc. Method of preparing polyester filament material
US5061281A (en) * 1985-12-17 1991-10-29 Allied-Signal Inc. Bioresorbable polymers and implantation devices thereof
US5110852A (en) * 1982-07-16 1992-05-05 Rijksuniversiteit Te Groningen Filament material polylactide mixtures
US5180392A (en) * 1988-02-01 1993-01-19 Einar Skeie Anastomotic device
WO1995003347A1 (en) * 1993-07-22 1995-02-02 Eastman Chemical Company Copolyesters having repeat units derived from succinic acid
US5403346A (en) * 1992-12-31 1995-04-04 Loeser; Edward A. Self-affixing suture assembly
US5527342A (en) * 1993-12-14 1996-06-18 Pietrzak; William S. Method and apparatus for securing soft tissues, tendons and ligaments to bone
WO1996022055A1 (en) 1995-01-19 1996-07-25 Inbae Yoon Surgical stapling system and method of applying staples from multiple staple cartridges
US5616681A (en) * 1994-11-01 1997-04-01 Nippon Shokubai Co., Ltd. Process for producing aliphatic polyester
US5632753A (en) * 1992-12-31 1997-05-27 Loeser; Edward A. Surgical procedures
US5843573A (en) * 1994-10-25 1998-12-01 Nippon Shokubai Co., Ltd. Polyester resin composition
WO2004108792A2 (en) * 2003-04-10 2004-12-16 Vinod Chintamani Malshe Novel biodegradable aliphatic polyesters and pharmaceutical compositions and applications thereof
DE19857067B4 (de) * 1997-12-15 2005-07-28 Ykk Corp. Verschlußelement aus biologisch abbaubarem Kunststoff

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2391710A2 (fr) * 1975-12-02 1978-12-22 Rhone Poulenc Ind Conduit chirurgical implantable
US4105034A (en) * 1977-06-10 1978-08-08 Ethicon, Inc. Poly(alkylene oxalate) absorbable coating for sutures
JPH01223969A (ja) * 1988-03-04 1989-09-07 Nippon Medical Supply Corp 被覆縫合糸
JP2589908B2 (ja) * 1992-05-13 1997-03-12 昭和高分子株式会社 ポリエステル製不織布
CA2136311A1 (en) * 1993-03-22 1994-09-29 Yoshiaki Iwaya Aliphatic polyesters and method of preparing the same

Citations (3)

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US2071250A (en) * 1931-07-03 1937-02-16 Du Pont Linear condensation polymers
US3463158A (en) * 1963-10-31 1969-08-26 American Cyanamid Co Polyglycolic acid prosthetic devices
US3620218A (en) * 1963-10-31 1971-11-16 American Cyanamid Co Cylindrical prosthetic devices of polyglycolic acid

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2071250A (en) * 1931-07-03 1937-02-16 Du Pont Linear condensation polymers
US3463158A (en) * 1963-10-31 1969-08-26 American Cyanamid Co Polyglycolic acid prosthetic devices
US3620218A (en) * 1963-10-31 1971-11-16 American Cyanamid Co Cylindrical prosthetic devices of polyglycolic acid

Cited By (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4080969A (en) * 1973-11-21 1978-03-28 American Cyanamid Company Suture or ligature carrying on the exposed surface thereof a coating of a polyester resin
US3960152A (en) * 1974-01-21 1976-06-01 American Cyanamid Company Surgical sutures of unsymmetrically substituted 1,4-dioxane-2,5-diones
US4128612A (en) * 1974-04-19 1978-12-05 American Cyanamid Company Making absorbable surgical felt
US4032993A (en) * 1974-06-28 1977-07-05 Rhone-Poulenc Industries Bioresorbable surgical articles
US4141087A (en) * 1977-01-19 1979-02-27 Ethicon, Inc. Isomorphic copolyoxalates and sutures thereof
US4186189A (en) * 1977-09-28 1980-01-29 Ethicon, Inc. Absorbable pharmaceutical compositions based on poly(alkylene oxalates)
US4411027A (en) * 1979-04-27 1983-10-25 University Of Medicine And Dentistry Of New Jersey Bio-absorbable composite tissue scaffold
US4329743A (en) * 1979-04-27 1982-05-18 College Of Medicine And Dentistry Of New Jersey Bio-absorbable composite tissue scaffold
US4529792A (en) * 1979-12-17 1985-07-16 Minnesota Mining And Manufacturing Company Process for preparing synthetic absorbable poly(esteramides)
US4343931A (en) * 1979-12-17 1982-08-10 Minnesota Mining And Manufacturing Company Synthetic absorbable surgical devices of poly(esteramides)
US4388926A (en) * 1980-12-22 1983-06-21 Ethicon, Inc. High compliance monofilament surgical sutures comprising poly[alkylene terephthalate-co-(2-alkenyl or alkyl)succinate]
US4396746A (en) * 1981-04-16 1983-08-02 Daicel Chemical Industries, Ltd. Thermoplastic polyester copolymer
DE3249111C2 (de) * 1981-10-09 1986-02-06 United States Surgical Corp., Norwalk, Conn. Chirurgische kunststoffartige Befestigungseinrichtung zum Festlegen von Körpergewebe
US4441496A (en) * 1982-02-08 1984-04-10 Ethicon, Inc. Copolymers of p-dioxanone and 2,5-morpholinediones and surgical devices formed therefrom having accelerated absorption characteristics
US5110852A (en) * 1982-07-16 1992-05-05 Rijksuniversiteit Te Groningen Filament material polylactide mixtures
US4915893A (en) * 1982-07-16 1990-04-10 Medtronic, Inc. Method of preparing polyester filament material
US4603695A (en) * 1983-07-05 1986-08-05 Japan Medical Supply Co., Ltd. Use of molded polymeric material for preventing adhesion of vital tissues
EP0144534A2 (en) * 1983-09-20 1985-06-19 Allied Corporation prosthetic devices
EP0144534A3 (en) * 1983-09-20 1986-12-17 Allied Corporation Prosthetic devices
US4670286A (en) * 1983-09-20 1987-06-02 Allied Corporation Method of forming prosthetic devices
US4594407A (en) * 1983-09-20 1986-06-10 Allied Corporation Prosthetic devices derived from krebs-cycle dicarboxylic acids and diols
US4481353A (en) * 1983-10-07 1984-11-06 The Children's Medical Center Corporation Bioresorbable polyesters and polyester composites
US4662884A (en) * 1984-04-25 1987-05-05 University Of Utah Research Foundation Prostheses and methods for promoting nerve regeneration
US4778467A (en) * 1984-04-25 1988-10-18 The University Of Utah Prostheses and methods for promoting nerve regeneration and for inhibiting the formation of neuromas
US4652264A (en) * 1985-04-25 1987-03-24 American Cyanamid Company Prosthetic tubular article
US4871365A (en) * 1985-04-25 1989-10-03 American Cyanamid Company Partially absorbable prosthetic tubular article having an external support
US5061281A (en) * 1985-12-17 1991-10-29 Allied-Signal Inc. Bioresorbable polymers and implantation devices thereof
US4773416A (en) * 1986-02-07 1988-09-27 Hourahane Donald H Surgery in horses
US4738255A (en) * 1986-04-07 1988-04-19 Biotron Labs, Inc. Suture anchor system
US4844067A (en) * 1987-02-19 1989-07-04 Japan Medical Supply Co., Ltd. Sucrose fatty acid ester coated suture
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IT1048160B (it) 1980-11-20
NO135968C (zh) 1977-07-06
SE396286B (sv) 1977-09-19
JPS5047492A (zh) 1975-04-26
ZA739015B (en) 1974-10-30
BR7309394D0 (pt) 1974-09-24
CH587659A5 (zh) 1977-05-13
GB1444817A (en) 1976-08-04
AU6295773A (en) 1975-05-29
DK131804B (da) 1975-09-08
NO135968B (zh) 1977-03-28
FR2208687B1 (zh) 1976-07-23
FR2208687A1 (zh) 1974-06-28
BE808088A (fr) 1974-05-30
NL7316072A (zh) 1974-06-05
CA1023493A (en) 1977-12-27
DK131804C (da) 1976-02-09
DE2359865A1 (de) 1974-06-06

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