CH543501A - Verfahren zur Herstellung von a-Glycolid - Google Patents
Verfahren zur Herstellung von a-GlycolidInfo
- Publication number
- CH543501A CH543501A CH856168A CH856168A CH543501A CH 543501 A CH543501 A CH 543501A CH 856168 A CH856168 A CH 856168A CH 856168 A CH856168 A CH 856168A CH 543501 A CH543501 A CH 543501A
- Authority
- CH
- Switzerland
- Prior art keywords
- glycolide
- temperature
- parts
- solvent
- mixture
- Prior art date
Links
- 238000002955 isolation Methods 0.000 title abstract description 4
- 238000012512 characterization method Methods 0.000 title abstract 2
- 239000002904 solvent Substances 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 27
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 22
- 239000000243 solution Substances 0.000 abstract description 14
- 238000006116 polymerization reaction Methods 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 238000001914 filtration Methods 0.000 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 3
- 238000001125 extrusion Methods 0.000 abstract description 3
- 239000012047 saturated solution Substances 0.000 abstract description 2
- 239000007787 solid Substances 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000007858 starting material Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229960004275 glycolic acid Drugs 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 description 2
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic alcohols Chemical class 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 206010000117 Abnormal behaviour Diseases 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N butenedioic acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64550267A | 1967-06-12 | 1967-06-12 | |
| CH1053567A CH482668A (de) | 1967-07-25 | 1967-07-25 | Verfahren zur Herstellung von a-Glycolid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH543501A true CH543501A (de) | 1973-12-14 |
Family
ID=24589277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH856168A CH543501A (de) | 1967-06-12 | 1968-06-10 | Verfahren zur Herstellung von a-Glycolid |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3457280A (ref) |
| BE (1) | BE714117A (ref) |
| CH (1) | CH543501A (ref) |
| DE (1) | DE1668993C3 (ref) |
| ES (1) | ES354952A1 (ref) |
| FR (1) | FR1560162A (ref) |
| NL (1) | NL159382B (ref) |
| SE (2) | SE356047B (ref) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3912692A (en) * | 1973-05-03 | 1975-10-14 | American Cyanamid Co | Process for polymerizing a substantially pure glycolide composition |
| US4716964A (en) * | 1981-08-10 | 1988-01-05 | Exxon Production Research Company | Use of degradable ball sealers to seal casing perforations in well treatment fluid diversion |
| US4727163A (en) * | 1985-07-11 | 1988-02-23 | E. I. Du Pont De Nemours And Company | Process for preparing highly pure cyclic esters |
| US4650851A (en) * | 1986-03-19 | 1987-03-17 | Pfizer Hospital Products Group, Inc. | Purification of glycolide |
| DE3781133T2 (de) * | 1986-12-19 | 1993-06-24 | Akzo Nv | Herstellung von polymilchsaeure und copolymeren daraus. |
| US4835293A (en) * | 1987-02-24 | 1989-05-30 | E. I. Du Pont De Nemours And Company | Atmospheric pressure process for preparing pure cyclic esters |
| US5319107A (en) * | 1990-09-18 | 1994-06-07 | Biopak Technology, Ltd. | Method to produce cyclic esters |
| US5274127A (en) * | 1990-09-18 | 1993-12-28 | Biopak Technology, Ltd. | Lactide production from dehydration of aqueous lactic acid feed |
| US5223630A (en) * | 1989-10-10 | 1993-06-29 | E. I. Du Pont De Nemours And Company | Glycolide purification process |
| US5043458A (en) * | 1990-05-03 | 1991-08-27 | E. I. Du Pont De Nemours And Company | One-step continuous process for preparing cyclic esters |
| US5332839A (en) * | 1990-09-18 | 1994-07-26 | Biopak Technology, Ltd. | Catalytic production of lactide directly from lactic acid |
| US5675021A (en) * | 1992-03-19 | 1997-10-07 | Chronopol, Inc. | Method to produce and purify cyclic esters |
| US5420304A (en) * | 1992-03-19 | 1995-05-30 | Biopak Technology, Ltd. | Method to produce cyclic esters |
| US5686630A (en) * | 1993-09-29 | 1997-11-11 | Chronopol, Inc. | Purifying cyclic esters by aqueous solvent extraction |
| US6074673A (en) * | 1996-04-22 | 2000-06-13 | Guillen; Manuel | Slow-release, self-absorbing, drug delivery system |
| PL1909973T3 (pl) | 2005-07-15 | 2019-01-31 | Micell Technologies, Inc. | Polimerowe powłoki zawierające proszek leku o kontrolowanej morfologii |
| US20090062909A1 (en) | 2005-07-15 | 2009-03-05 | Micell Technologies, Inc. | Stent with polymer coating containing amorphous rapamycin |
| EP2944382A1 (en) | 2006-04-26 | 2015-11-18 | Micell Technologies, Inc. | Coatings containing multiple drugs |
| US9539593B2 (en) | 2006-10-23 | 2017-01-10 | Micell Technologies, Inc. | Holder for electrically charging a substrate during coating |
| CA2679712C (en) | 2007-01-08 | 2016-11-15 | Micell Technologies, Inc. | Stents having biodegradable layers |
| US11426494B2 (en) | 2007-01-08 | 2022-08-30 | MT Acquisition Holdings LLC | Stents having biodegradable layers |
| WO2008148013A1 (en) | 2007-05-25 | 2008-12-04 | Micell Technologies, Inc. | Polymer films for medical device coating |
| MX350637B (es) | 2008-04-17 | 2017-09-11 | Micell Technologies Inc | Stents que tienen capas bioabsorbibles. |
| CA2730995C (en) | 2008-07-17 | 2016-11-22 | Micell Technologies, Inc. | Drug delivery medical device |
| US8834913B2 (en) | 2008-12-26 | 2014-09-16 | Battelle Memorial Institute | Medical implants and methods of making medical implants |
| EP2413847A4 (en) | 2009-04-01 | 2013-11-27 | Micell Technologies Inc | COATED STENTS |
| CA2759015C (en) | 2009-04-17 | 2017-06-20 | James B. Mcclain | Stents having controlled elution |
| EP2453834A4 (en) | 2009-07-16 | 2014-04-16 | Micell Technologies Inc | MEDICAL DEVICE DISPENSING MEDICINE |
| EP2531140B1 (en) | 2010-02-02 | 2017-11-01 | Micell Technologies, Inc. | Stent and stent delivery system with improved deliverability |
| US8795762B2 (en) | 2010-03-26 | 2014-08-05 | Battelle Memorial Institute | System and method for enhanced electrostatic deposition and surface coatings |
| CA2797110C (en) | 2010-04-22 | 2020-07-21 | Micell Technologies, Inc. | Stents and other devices having extracellular matrix coating |
| CA2805631C (en) | 2010-07-16 | 2018-07-31 | Micell Technologies, Inc. | Drug delivery medical device |
| WO2012166819A1 (en) | 2011-05-31 | 2012-12-06 | Micell Technologies, Inc. | System and process for formation of a time-released, drug-eluting transferable coating |
| US10117972B2 (en) | 2011-07-15 | 2018-11-06 | Micell Technologies, Inc. | Drug delivery medical device |
| US10188772B2 (en) | 2011-10-18 | 2019-01-29 | Micell Technologies, Inc. | Drug delivery medical device |
| CN105307597A (zh) | 2013-03-12 | 2016-02-03 | 脉胜医疗技术公司 | 可生物吸收的生物医学植入物 |
| EP2996629B1 (en) | 2013-05-15 | 2021-09-22 | Micell Technologies, Inc. | Bioabsorbable biomedical implants |
| CN110684011B (zh) * | 2018-07-06 | 2021-02-09 | 中国石油化工股份有限公司 | 乙交酯的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2668162A (en) * | 1952-03-20 | 1954-02-02 | Du Pont | Preparation of high molecular weight polyhydroxyacetic ester |
-
1967
- 1967-06-12 US US645502A patent/US3457280A/en not_active Expired - Lifetime
-
1968
- 1968-03-05 DE DE1668993A patent/DE1668993C3/de not_active Expired
- 1968-04-19 FR FR1560162D patent/FR1560162A/fr not_active Expired
- 1968-04-24 BE BE714117D patent/BE714117A/xx unknown
- 1968-05-08 NL NL6806492.A patent/NL159382B/xx not_active IP Right Cessation
- 1968-06-10 CH CH856168A patent/CH543501A/de not_active IP Right Cessation
- 1968-06-12 SE SE07911/68A patent/SE356047B/xx unknown
- 1968-06-12 SE SE7111003A patent/SE378597B/xx unknown
- 1968-06-12 ES ES354952A patent/ES354952A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES354952A1 (es) | 1970-03-01 |
| FR1560162A (ref) | 1969-03-14 |
| NL159382B (nl) | 1979-02-15 |
| NL6806492A (ref) | 1968-12-13 |
| DE1668993A1 (de) | 1972-03-23 |
| SE356047B (ref) | 1973-05-14 |
| BE714117A (ref) | 1968-10-24 |
| DE1668993C3 (de) | 1974-02-07 |
| SE378597B (ref) | 1975-09-08 |
| DE1668993B2 (de) | 1973-07-12 |
| US3457280A (en) | 1969-07-22 |
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