CA1123984A - Copolymeres sequences de lactide et de glycolide et protheses chirurgicales - Google Patents
Copolymeres sequences de lactide et de glycolide et protheses chirurgicalesInfo
- Publication number
- CA1123984A CA1123984A CA314,425A CA314425A CA1123984A CA 1123984 A CA1123984 A CA 1123984A CA 314425 A CA314425 A CA 314425A CA 1123984 A CA1123984 A CA 1123984A
- Authority
- CA
- Canada
- Prior art keywords
- lactide
- percent
- glycolide
- polymer
- copolymer
- 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
Links
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 title claims abstract description 67
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 28
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 title claims description 49
- 229920001577 copolymer Polymers 0.000 claims abstract description 26
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 claims abstract description 11
- 229920000642 polymer Polymers 0.000 claims description 59
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 14
- 239000000835 fiber Substances 0.000 claims description 11
- 238000010521 absorption reaction Methods 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- -1 alicyclic diol Chemical class 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 238000001727 in vivo Methods 0.000 claims description 8
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 7
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 150000002009 diols Chemical class 0.000 claims description 6
- 239000004744 fabric Substances 0.000 claims description 6
- 230000014759 maintenance of location Effects 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 3
- 229940035437 1,3-propanediol Drugs 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 238000005304 joining Methods 0.000 claims description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- JJTUDXZGHPGLLC-QWWZWVQMSA-N (3r,6r)-3,6-dimethyl-1,4-dioxane-2,5-dione Chemical compound C[C@H]1OC(=O)[C@@H](C)OC1=O JJTUDXZGHPGLLC-QWWZWVQMSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims 2
- 238000002360 preparation method Methods 0.000 abstract description 11
- 239000000203 mixture Substances 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 229920005604 random copolymer Polymers 0.000 description 11
- 229920000954 Polyglycolide Polymers 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- PBDYZRHIIXZUCS-UHFFFAOYSA-N 2-[3-(1,3-dioxoisoindole-2-carbonyl)benzoyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(=O)C1=CC(C(N2C(C3=CC=CC=C3C2=O)=O)=O)=CC=C1 PBDYZRHIIXZUCS-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 239000012632 extractable Substances 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229940074731 ophthalmologic surgical aids Drugs 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 238000009941 weaving Methods 0.000 description 2
- IOGGBUVFUGPCLQ-UHFFFAOYSA-N 1-[4-(2-oxoazepane-1-carbonyl)benzoyl]azepan-2-one Chemical compound C=1C=C(C(=O)N2C(CCCCC2)=O)C=CC=1C(=O)N1CCCCCC1=O IOGGBUVFUGPCLQ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 206010019909 Hernia Diseases 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 238000012661 block copolymerization Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009950 felting Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 239000002650 laminated plastic Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229940058401 polytetrafluoroethylene Drugs 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B17/00—Surgical instruments, devices or methods, e.g. tourniquets
- A61B17/04—Surgical instruments, devices or methods, e.g. tourniquets for suturing wounds; Holders or packages for needles or suture materials
- A61B17/06—Needles ; Sutures; Needle-suture combinations; Holders or packages for needles or suture materials
- A61B17/06166—Sutures
-
- 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
-
- 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
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B17/00—Surgical instruments, devices or methods, e.g. tourniquets
- A61B2017/00004—(bio)absorbable, (bio)resorbable or resorptive
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Polymers & Plastics (AREA)
- Medical Informatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Materials For Medical Uses (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85218577A | 1977-11-16 | 1977-11-16 | |
| US852,185 | 1977-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1123984A true CA1123984A (fr) | 1982-05-18 |
Family
ID=25312683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA314,425A Expired CA1123984A (fr) | 1977-11-16 | 1978-10-26 | Copolymeres sequences de lactide et de glycolide et protheses chirurgicales |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA1123984A (fr) |
| DE (1) | DE2849785A1 (fr) |
| FR (1) | FR2409278A1 (fr) |
| GB (1) | GB2008135B (fr) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2917446A1 (de) * | 1979-04-28 | 1980-11-06 | Merck Patent Gmbh | Chirurgisches material |
| IE52535B1 (en) * | 1981-02-16 | 1987-12-09 | Ici Plc | Continuous release pharmaceutical compositions |
| US4689424A (en) * | 1981-08-06 | 1987-08-25 | Ethicon, Inc. | Radiation sterilizable absorbable polymeric materials and methods for manufacturing the same |
| ATE37983T1 (de) * | 1982-04-22 | 1988-11-15 | Ici Plc | Mittel mit verzoegerter freigabe. |
| US4429080A (en) * | 1982-07-01 | 1984-01-31 | American Cyanamid Company | Synthetic copolymer surgical articles and method of manufacturing the same |
| US4595713A (en) * | 1985-01-22 | 1986-06-17 | Hexcel Corporation | Medical putty for tissue augmentation |
| US4741337A (en) * | 1985-07-17 | 1988-05-03 | Ethicon, Inc. | Surgical fastener made from glycolide-rich polymer blends |
| JPS63109851A (ja) * | 1986-06-02 | 1988-05-14 | 三井東圧化学株式会社 | 縫合糸の保存方法 |
| DE3644588C1 (de) * | 1986-12-27 | 1988-03-10 | Ethicon Gmbh | Implantat und Verfahren zu seiner Herstellung |
| DE3801426A1 (de) * | 1988-01-20 | 1989-08-03 | Ethicon Gmbh | Filzartiges implantat |
| DE3803435C1 (en) * | 1988-02-05 | 1989-09-21 | Ethicon Gmbh & Co Kg, 2000 Norderstedt, De | Implanted splint for rib fractures |
| US5250584A (en) * | 1988-08-31 | 1993-10-05 | G-C Dental Industrial Corp. | Periodontium-regenerative materials |
| DE3830481A1 (de) * | 1988-09-08 | 1990-03-22 | Ethicon Gmbh | Schlauchfoermiges implantat, sowie verfahren zu dessen herstellung |
| DE3830005C1 (en) * | 1988-08-31 | 1989-11-02 | Ethicon Gmbh & Co Kg, 2000 Norderstedt, De | Sheet-like implant |
| JP2709349B2 (ja) * | 1988-08-31 | 1998-02-04 | 株式会社 ジーシー | 歯周組織再生用素材 |
| DE4012602C2 (de) | 1990-04-20 | 1994-06-09 | Ethicon Gmbh | Implantat-Kordel |
| US6353030B1 (en) | 1990-08-01 | 2002-03-05 | Novartis Ag | Relating to organic compounds |
| DE4218510A1 (de) * | 1992-06-02 | 1993-12-09 | Pharmatech Gmbh | Verfahren zur Herstellung biologisch abbaubarer Polyester |
| US5236444A (en) * | 1992-10-27 | 1993-08-17 | United States Surgical Corporation | Absorbable polymers and surgical articles made therefrom |
| JP3588907B2 (ja) * | 1996-03-22 | 2004-11-17 | トヨタ自動車株式会社 | ポリ乳酸の製造方法 |
| CA2250760A1 (fr) * | 1996-04-01 | 1997-10-09 | American Cyanamid Company | Copolymeres cristallins et procede de production de ces copolymeres |
| US6007565A (en) * | 1997-09-05 | 1999-12-28 | United States Surgical | Absorbable block copolymers and surgical articles fabricated therefrom |
| US6287499B1 (en) * | 1998-10-09 | 2001-09-11 | United States Surgical Corporation | Process of making bioabsorbable block copolymer filaments |
| US6264674B1 (en) | 1998-11-09 | 2001-07-24 | Robert L. Washington | Process for hot stretching braided ligatures |
| DE19912360A1 (de) * | 1999-03-19 | 2000-09-21 | Aesculap Ag & Co Kg | Strangförmiges Implantat aus resorbierbarem Polymermaterial, Verfahren zu seiner Herstellung und Anwendung in der Chirurgie |
| US6045571A (en) * | 1999-04-14 | 2000-04-04 | Ethicon, Inc. | Multifilament surgical cord |
| US8652506B2 (en) * | 2008-06-05 | 2014-02-18 | Boston Scientific Scimed, Inc. | Bio-degradable block co-polymers for controlled release |
| CN115505106B (zh) * | 2021-06-22 | 2024-04-05 | 上海浦景化工技术股份有限公司 | 一种耐老化聚乙醇酸的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4140678A (en) * | 1977-06-13 | 1979-02-20 | Ethicon, Inc. | Synthetic absorbable surgical devices of poly(alkylene oxalates) |
-
1978
- 1978-10-26 CA CA314,425A patent/CA1123984A/fr not_active Expired
- 1978-11-10 FR FR7831783A patent/FR2409278A1/fr active Granted
- 1978-11-15 GB GB7844540A patent/GB2008135B/en not_active Expired
- 1978-11-16 DE DE19782849785 patent/DE2849785A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2409278A1 (fr) | 1979-06-15 |
| GB2008135A (en) | 1979-05-31 |
| GB2008135B (en) | 1982-04-28 |
| DE2849785C2 (fr) | 1987-11-12 |
| FR2409278B1 (fr) | 1983-05-13 |
| DE2849785A1 (de) | 1979-05-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |