CA2158420C - Absorbable polymer and surgical articles fabricated therefrom - Google Patents
Absorbable polymer and surgical articles fabricated therefrom Download PDFInfo
- Publication number
- CA2158420C CA2158420C CA002158420A CA2158420A CA2158420C CA 2158420 C CA2158420 C CA 2158420C CA 002158420 A CA002158420 A CA 002158420A CA 2158420 A CA2158420 A CA 2158420A CA 2158420 C CA2158420 C CA 2158420C
- Authority
- CA
- Canada
- Prior art keywords
- dioxane
- suture
- monofilament
- random copolymer
- mole percent
- 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.)
- Expired - Fee Related
Links
- 229920000642 polymer Polymers 0.000 title description 3
- VPVXHAANQNHFSF-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical compound O=C1COCCO1 VPVXHAANQNHFSF-UHFFFAOYSA-N 0.000 claims abstract description 39
- 229920001577 copolymer Polymers 0.000 claims abstract description 36
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229920005604 random copolymer Polymers 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 18
- 238000000137 annealing Methods 0.000 claims description 11
- 238000001125 extrusion Methods 0.000 claims description 10
- 230000001747 exhibiting effect Effects 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 4
- 238000007710 freezing Methods 0.000 claims description 4
- 230000008014 freezing Effects 0.000 claims description 4
- 230000012010 growth Effects 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- 230000003872 anastomosis Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 238000004804 winding Methods 0.000 claims 1
- 239000000178 monomer Substances 0.000 abstract description 7
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 230000014759 maintenance of location Effects 0.000 description 8
- 230000000704 physical effect Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000010791 quenching Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 206010052428 Wound Diseases 0.000 description 5
- 208000027418 Wounds and injury Diseases 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 239000003102 growth factor Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- ANLVEXKNRYNLDH-UHFFFAOYSA-N 1,3-dioxonan-2-one Chemical compound O=C1OCCCCCCO1 ANLVEXKNRYNLDH-UHFFFAOYSA-N 0.000 description 2
- MFRCZYUUKMFJQJ-UHFFFAOYSA-N 1,4-dioxane-2,5-dione;1,3-dioxan-2-one Chemical compound O=C1OCCCO1.O=C1COC(=O)CO1 MFRCZYUUKMFJQJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 229920002988 biodegradable polymer Polymers 0.000 description 2
- 239000004621 biodegradable polymer Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 229940096890 d&c violet no. 2 Drugs 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229920002463 poly(p-dioxanone) polymer Polymers 0.000 description 2
- 239000000622 polydioxanone Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 230000008467 tissue growth Effects 0.000 description 2
- WTRBJJXKZUJRBA-UHFFFAOYSA-N 1,3-dioxacyclopentadecan-2-one Chemical compound O=C1OCCCCCCCCCCCCO1 WTRBJJXKZUJRBA-UHFFFAOYSA-N 0.000 description 1
- BNKAOFCGRFIIHY-UHFFFAOYSA-N 1,3-dioxacyclotridecan-2-one Chemical compound O=C1OCCCCCCCCCCO1 BNKAOFCGRFIIHY-UHFFFAOYSA-N 0.000 description 1
- LGCNDZIFJKHQHB-UHFFFAOYSA-N 1,3-dioxacycloundecan-2-one Chemical compound O=C1OCCCCCCCCO1 LGCNDZIFJKHQHB-UHFFFAOYSA-N 0.000 description 1
- GQQFGLUEAGQQJA-UHFFFAOYSA-N 1,3-dioxecan-2-one Chemical compound O=C1OCCCCCCCO1 GQQFGLUEAGQQJA-UHFFFAOYSA-N 0.000 description 1
- VKSWWACDZPRJAP-UHFFFAOYSA-N 1,3-dioxepan-2-one Chemical compound O=C1OCCCCO1 VKSWWACDZPRJAP-UHFFFAOYSA-N 0.000 description 1
- 208000031504 Asymptomatic Infections Diseases 0.000 description 1
- 108010071942 Colony-Stimulating Factors Proteins 0.000 description 1
- 102000009024 Epidermal Growth Factor Human genes 0.000 description 1
- 101800003838 Epidermal growth factor Proteins 0.000 description 1
- 102000018233 Fibroblast Growth Factor Human genes 0.000 description 1
- 108050007372 Fibroblast Growth Factor Proteins 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- 102000002068 Glycopeptides Human genes 0.000 description 1
- 108010015899 Glycopeptides Proteins 0.000 description 1
- 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 1
- 101000947178 Homo sapiens Platelet basic protein Proteins 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 102100020873 Interleukin-2 Human genes 0.000 description 1
- 108010002350 Interleukin-2 Proteins 0.000 description 1
- 108060003100 Magainin Proteins 0.000 description 1
- 102100036154 Platelet basic protein Human genes 0.000 description 1
- 102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 1
- 108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 102000003978 Tissue Plasminogen Activator Human genes 0.000 description 1
- 108090000373 Tissue Plasminogen Activator Proteins 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 1
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 1
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 230000008468 bone growth Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940116977 epidermal growth factor Drugs 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229940126864 fibroblast growth factor Drugs 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- TVRGPOFMYCMNRB-UHFFFAOYSA-N quinizarine green ss Chemical compound C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1 TVRGPOFMYCMNRB-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000807 solvent casting Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/62—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters
- D01F6/625—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters derived from hydroxy-carboxylic acids, e.g. lactones
-
- 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
- A61L17/12—Homopolymers or copolymers of glycolic acid or lactic acid
-
- 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
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D10/00—Physical treatment of artificial filaments or the like during manufacture, i.e. during a continuous production process before the filaments have been collected
- D01D10/02—Heat treatment
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Surgery (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Textile Engineering (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Mechanical Engineering (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30795494A | 1994-09-16 | 1994-09-16 | |
| US08/307,954 | 1994-09-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2158420A1 CA2158420A1 (en) | 1996-03-17 |
| CA2158420C true CA2158420C (en) | 2007-05-01 |
Family
ID=23191888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002158420A Expired - Fee Related CA2158420C (en) | 1994-09-16 | 1995-09-15 | Absorbable polymer and surgical articles fabricated therefrom |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0701823B1 (Direct) |
| CA (1) | CA2158420C (Direct) |
| DE (1) | DE69529130T2 (Direct) |
| ES (1) | ES2188631T3 (Direct) |
Family Cites Families (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2683136A (en) | 1950-10-25 | 1954-07-06 | Du Pont | Copolymers of hydroxyacetic acid with other alcohol acids |
| US2703316A (en) | 1951-06-05 | 1955-03-01 | Du Pont | Polymers of high melting lactide |
| US2668162A (en) | 1952-03-20 | 1954-02-02 | Du Pont | Preparation of high molecular weight polyhydroxyacetic ester |
| US2758987A (en) | 1952-06-05 | 1956-08-14 | Du Pont | Optically active homopolymers containing but one antipodal species of an alpha-monohydroxy monocarboxylic acid |
| US3225766A (en) | 1962-03-26 | 1965-12-28 | Grace W R & Co | Method of making absorbable surgical sutures from poly beta hydroxy acids |
| NL294714A (Direct) | 1963-06-28 | |||
| US3739773A (en) | 1963-10-31 | 1973-06-19 | American Cyanamid Co | Polyglycolic acid prosthetic devices |
| 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 |
| US3297033A (en) | 1963-10-31 | 1967-01-10 | American Cyanamid Co | Surgical sutures |
| US3268487A (en) | 1963-12-23 | 1966-08-23 | Shell Oil Co | Process for polymerization of lactides |
| US3531561A (en) | 1965-04-20 | 1970-09-29 | Ethicon Inc | Suture preparation |
| US3442871A (en) | 1966-05-04 | 1969-05-06 | American Cyanamid Co | Process for polymerizing a glycolide |
| US3468853A (en) | 1966-06-15 | 1969-09-23 | American Cyanamid Co | Process of polymerizing a glycolide |
| US3565869A (en) | 1968-12-23 | 1971-02-23 | American Cyanamid Co | Extrudable and stretchable polyglycolic acid and process for preparing same |
| US3626948A (en) | 1968-12-23 | 1971-12-14 | American Cyanamid Co | Absorbable polyglycolic acid suture of enhanced in-vivo strength retention |
| US3797499A (en) | 1970-05-13 | 1974-03-19 | Ethicon Inc | Polylactide fabric graphs for surgical implantation |
| BE758156R (fr) | 1970-05-13 | 1971-04-28 | Ethicon Inc | Element de suture absorbable et sa |
| US3846382A (en) | 1971-02-25 | 1974-11-05 | American Cyanamid Co | Sterile medical dusting powder |
| US3781349A (en) | 1971-02-25 | 1973-12-25 | American Cyanamid Co | Preparation of polyglycolic acid in finely divided form |
| US3987937A (en) | 1971-05-06 | 1976-10-26 | Eppco | Powder feeder and methods for transporting particulate material |
| US3878284A (en) | 1971-08-12 | 1975-04-15 | American Cyanamid Co | Processes for making shaped articles such as filaments or films from solutions of polyglycolic acid |
| US3733919A (en) | 1971-09-20 | 1973-05-22 | Adjustable eccentric bearing mountings background | |
| US3867190A (en) | 1971-10-18 | 1975-02-18 | American Cyanamid Co | Reducing capillarity of polyglycolic acid sutures |
| US3736646A (en) | 1971-10-18 | 1973-06-05 | American Cyanamid Co | Method of attaching surgical needles to multifilament polyglycolic acid absorbable sutures |
| US3784585A (en) | 1971-10-21 | 1974-01-08 | American Cyanamid Co | Water-degradable resins containing recurring,contiguous,polymerized glycolide units and process for preparing same |
| US3792010A (en) | 1972-03-27 | 1974-02-12 | Ethicon Inc | Plasticized polyester sutures |
| US3982543A (en) | 1973-04-24 | 1976-09-28 | American Cyanamid Company | Reducing capillarity of polyglycolic acid sutures |
| US4033938A (en) | 1974-01-21 | 1977-07-05 | American Cyanamid Company | Polymers of unsymmetrically substituted 1,4-dioxane-2,5-diones |
| US3937223A (en) | 1974-04-19 | 1976-02-10 | American Cyanamid Company | Compacted surgical hemostatic felt |
| US3896802A (en) | 1974-04-19 | 1975-07-29 | American Cyanamid Co | Flexible flocked dressing |
| US4057537A (en) | 1975-01-28 | 1977-11-08 | Gulf Oil Corporation | Copolymers of L-(-)-lactide and epsilon caprolactone |
| US4045418A (en) | 1975-01-28 | 1977-08-30 | Gulf Oil Corporation | Copolymers of D,L-lactide and epsilon caprolactone |
| US4300565A (en) | 1977-05-23 | 1981-11-17 | American Cyanamid Company | Synthetic polyester surgical articles |
| US4243775A (en) | 1978-11-13 | 1981-01-06 | American Cyanamid Company | Synthetic polyester surgical articles |
| US4137921A (en) | 1977-06-24 | 1979-02-06 | Ethicon, Inc. | Addition copolymers of lactide and glycolide and method of preparation |
| US4246904A (en) | 1979-01-29 | 1981-01-27 | American Cyanamid Company | Surgical suture derived from segmented polyether-ester block copolymers |
| FR2439003A1 (fr) | 1978-10-20 | 1980-05-16 | Anvar | Nouvelles pieces d'osteosynthese, leur preparation et leur application |
| US4273920A (en) | 1979-09-12 | 1981-06-16 | Eli Lilly And Company | Polymerization process and product |
| US4744365A (en) | 1986-07-17 | 1988-05-17 | United States Surgical Corporation | Two-phase compositions for absorbable surgical devices |
| US4916193A (en) * | 1987-12-17 | 1990-04-10 | Allied-Signal Inc. | Medical devices fabricated totally or in part from copolymers of recurring units derived from cyclic carbonates and lactides |
| US5152781A (en) * | 1987-12-17 | 1992-10-06 | Allied-Signal Inc. | Medical devices fabricated from homopolymers and copolymers having recurring carbonate units |
| US5145945A (en) * | 1987-12-17 | 1992-09-08 | Allied-Signal Inc. | Homopolymers and copolymers having recurring carbonate units |
| WO1989005664A1 (en) * | 1987-12-17 | 1989-06-29 | Allied-Signal Inc. | Medical devices fabricated from homopolymers and copolymers having recurring carbonate units |
| US4891263A (en) * | 1987-12-17 | 1990-01-02 | Allied-Signal Inc. | Polycarbonate random copolymer-based fiber compositions and method of melt-spinning same and device |
| US4902203A (en) * | 1988-11-03 | 1990-02-20 | Sager Harold W | Housing for dual outlet, dual rotor blower |
| US5037950A (en) * | 1990-02-09 | 1991-08-06 | Ethicon, Inc. | Bioabsorbable copolymers of polyalkylene carbonate/RHO-dioxanone for sutures and coatings |
| US5322925A (en) * | 1992-10-30 | 1994-06-21 | United States Surgical Corporation | Absorbable block copolymers and surgical articles made therefrom |
| US5403347A (en) * | 1993-05-27 | 1995-04-04 | United States Surgical Corporation | Absorbable block copolymers and surgical articles fabricated therefrom |
| US5494620A (en) * | 1993-11-24 | 1996-02-27 | United States Surgical Corporation | Method of manufacturing a monofilament suture |
| US5391707A (en) * | 1993-12-10 | 1995-02-21 | United States Surgical Corporation | Process for the production of dioxanone |
-
1995
- 1995-09-15 CA CA002158420A patent/CA2158420C/en not_active Expired - Fee Related
- 1995-09-18 DE DE69529130T patent/DE69529130T2/de not_active Expired - Lifetime
- 1995-09-18 EP EP95114659A patent/EP0701823B1/en not_active Expired - Lifetime
- 1995-09-18 ES ES95114659T patent/ES2188631T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0701823A2 (en) | 1996-03-20 |
| DE69529130D1 (de) | 2003-01-23 |
| DE69529130T2 (de) | 2003-07-31 |
| CA2158420A1 (en) | 1996-03-17 |
| EP0701823A3 (Direct) | 1996-04-24 |
| ES2188631T3 (es) | 2003-07-01 |
| EP0701823B1 (en) | 2002-12-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140916 |
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| MKLA | Lapsed |
Effective date: 20140916 |