FI89505B - Foerfarande foer framstaellning av polyestrar - Google Patents
Foerfarande foer framstaellning av polyestrar Download PDFInfo
- Publication number
- FI89505B FI89505B FI871564A FI871564A FI89505B FI 89505 B FI89505 B FI 89505B FI 871564 A FI871564 A FI 871564A FI 871564 A FI871564 A FI 871564A FI 89505 B FI89505 B FI 89505B
- Authority
- FI
- Finland
- Prior art keywords
- polyester
- acid
- molecular weight
- product
- polydispersity
- Prior art date
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 86
- 238000000034 method Methods 0.000 claims abstract description 26
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 20
- 230000007062 hydrolysis Effects 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 18
- 238000009826 distribution Methods 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000002474 experimental method Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 7
- 239000004793 Polystyrene Substances 0.000 claims description 6
- 229920002223 polystyrene Polymers 0.000 claims description 6
- 238000001542 size-exclusion chromatography Methods 0.000 claims description 6
- 239000011260 aqueous acid Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 3
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 2
- 239000004626 polylactic acid Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 6
- 239000007864 aqueous solution Substances 0.000 claims 4
- 239000008267 milk Substances 0.000 claims 1
- 210000004080 milk Anatomy 0.000 claims 1
- 235000013336 milk Nutrition 0.000 claims 1
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 abstract 1
- 239000000047 product Substances 0.000 description 35
- 229920000642 polymer Polymers 0.000 description 17
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 12
- 229920001244 Poly(D,L-lactide) Polymers 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229960000448 lactic acid Drugs 0.000 description 6
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000007863 gel particle Substances 0.000 description 5
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 5
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 229920001634 Copolyester Polymers 0.000 description 3
- 238000011088 calibration curve Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229920000229 biodegradable polyester Polymers 0.000 description 2
- 239000004622 biodegradable polyester Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- 150000002605 large molecules Chemical class 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000013268 sustained release Methods 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- 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
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/912—Polymers modified by chemical after-treatment derived from hydroxycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyesters Or Polycarbonates (AREA)
- Steroid Compounds (AREA)
- Light Receiving Elements (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (7)
1. Förfarande för framställning av en polyester med vilken som heist numerisk medelmolekylvikt Mn som är mind- 5 re än cirka 20 000 mätt medelst uteslutningskromatografik enligt storlek i förhctllande tili polystyrenstandarder, kännetecknat därav, att förfarandet omfattar en hydrolys, som sker med en vattenlösning av en syra och som innebär en hydrolys av en polyester med samma kemiska 10 sammansättning som den önskade polyestern, men med en hög-re numerisk medelmolekylvikt Mn° än den önskade polyester-produkten, mätt pä ovanbestämda sätt, och hydrolysen sker under en tidsperiod t och tiden bestäms enligt formeln: 15 11 = Kt Mn Mn° där K är en konstant, som bestämts tidigare medelst ett 20 kalibreringsexperiment genom att använda en viss polyester, en viss vatten-, syra- och polyesterkoncentration och en viss önskad hydrolystemperatur.
2. Förfarande enligt patentkravet 1, kännetecknat därav, att polyestern är en polymjölksyra 25 eller en poly(mjölk-sam-glykol)syra.
3. Förfarande enligt patentkravet 2, kännetecknat därav, att den vattenhaltiga syran är ät-tiksyra.
4. Förfarande enligt patentkravet 1 för framställ-30 ning av en polyesterprodukt med en polydispersitetsgrad högre än cirka 2,5, kännetecknat därav, att en lösning, som innehäller utgängsmaterial för polyester, vars polydispersitetsgrad är cirka 2 och som befinner sig vid omgivningens temperatur i vattenlösningen av syran, 35 tillsätts med konstant hastighet under förutbestämda tid t i ett reaktionskärl, som uppvärmts tillräckligt, för att i 17 -^9 505 polyesterlösningen skall kunna bringas i äterflödeskyl-temperatur dä den tillsätts.
5. Förfarande enligt patentkravet 1 för framställ-ning av en polyesterprodukt med en mycket vidsträckt mole- 5 kylviktfördelning och en polydispersitetsgrad högre än 2,5, kännetecknat därav, att lösningen, som innehäller utgängsmaterial för polyester, vars polydispersitetsgrad är cirka 2 och som befinner sig vid omgivning-ens temperatur i vattenlösningen av syran, tillsätts med 10 växande hastighet under tid t i ett reaktionskärl, som uppvärmts tillräckligt, för att polyesterlösningen skall kunna bringas i äterflödeskyltemperatur, dä den tillsätts.
6. Förfarande enligt patentkravet 1 för framställ-ning av en polyesterprodukt med mängnodmolekylviktfördel- 15 ning, kännetecknat därav, att en lösning, som innehäller utgängsmaterial för polyester vid omgivningens temperatur i vattenlösningen av syran, tillsätts med be-stämda tidsintervaller i tvä eller flera portioner i ett reaktionskärl, som uppvärmts tillräckligt, för att polyes-20 terlösningen skall kunna bringas i äterflödeskyltempera-tur, da den tillsätts.
7. Förfarande enligt patentkravet 1 för framställ-ning av en polyesterprodukt med en polydispersitetsgrad mindre än cirka 1,5, kännetecknat därav, att 25 utgängspolyestern har en likadan polydispersitetsgrad som den önskade produkten och Mn° ej är större än cirka 5 gänger den önskade produktens Mn.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868609537A GB8609537D0 (en) | 1986-04-18 | 1986-04-18 | Polyesters |
| GB8609537 | 1986-04-18 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI871564A0 FI871564A0 (fi) | 1987-04-09 |
| FI871564A FI871564A (fi) | 1987-10-19 |
| FI89505B true FI89505B (fi) | 1993-06-30 |
| FI89505C FI89505C (sv) | 1993-10-11 |
Family
ID=10596456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI871564A FI89505C (sv) | 1986-04-18 | 1987-04-09 | Förfarande för framställning av polyestrar |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4789726A (sv) |
| EP (1) | EP0244114B1 (sv) |
| JP (1) | JP2553076B2 (sv) |
| AT (1) | ATE52268T1 (sv) |
| AU (1) | AU595594B2 (sv) |
| CA (1) | CA1279148C (sv) |
| DE (1) | DE3762421D1 (sv) |
| DK (1) | DK167195B1 (sv) |
| ES (1) | ES2014474B3 (sv) |
| FI (1) | FI89505C (sv) |
| GB (1) | GB8609537D0 (sv) |
| GR (1) | GR3001199T3 (sv) |
| HU (1) | HU197032B (sv) |
| IE (1) | IE59961B1 (sv) |
| IL (1) | IL82032A (sv) |
| NO (1) | NO169017C (sv) |
| NZ (1) | NZ220011A (sv) |
| PT (1) | PT84682B (sv) |
| ZA (1) | ZA872206B (sv) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3708915C2 (de) * | 1987-03-19 | 1996-04-04 | Boehringer Ingelheim Kg | Verfahren zur Herstellung von Lactid |
| JPH0613602B2 (ja) * | 1987-07-14 | 1994-02-23 | 三井東圧化学株式会社 | ｄ▲ｌ▼−乳酸−グリコール酸共重合物の製造方法 |
| US5424346A (en) * | 1988-08-08 | 1995-06-13 | Ecopol, Llc | Biodegradable replacement of crystal polystyrene |
| US5180765A (en) * | 1988-08-08 | 1993-01-19 | Biopak Technology, Ltd. | Biodegradable packaging thermoplastics from lactides |
| DE3936191C2 (de) * | 1989-10-31 | 1996-10-17 | Boehringer Ingelheim Kg | Neue Copolymere aus Milchsäure und Weinsäure, ihre Herstellung sowie ihre Verwendung |
| JPH04226125A (ja) * | 1990-06-23 | 1992-08-14 | Boehringer Ingelheim Kg | ポリ−ｄ，ｌ−ラクチドの製造方法及び活性物質の担体としてのそれらの使用 |
| US5486362A (en) * | 1991-05-07 | 1996-01-23 | Dynagen, Inc. | Controlled, sustained release delivery system for treating drug dependency |
| US5403595A (en) * | 1991-05-07 | 1995-04-04 | Dynagen, Inc. | Controlled, sustained release delivery system for smoking cessation |
| ZA924811B (en) * | 1991-06-28 | 1993-12-29 | Endorecherche Inc | Controlled release systems and low dose androgens |
| US5258488A (en) * | 1992-01-24 | 1993-11-02 | Cargill, Incorporated | Continuous process for manufacture of lactide polymers with controlled optical purity |
| US6326458B1 (en) | 1992-01-24 | 2001-12-04 | Cargill, Inc. | Continuous process for the manufacture of lactide and lactide polymers |
| US6005067A (en) | 1992-01-24 | 1999-12-21 | Cargill Incorporated | Continuous process for manufacture of lactide polymers with controlled optical purity |
| US5247059A (en) * | 1992-01-24 | 1993-09-21 | Cargill, Incorporated | Continuous process for the manufacture of a purified lactide from esters of lactic acid |
| US5247058A (en) * | 1992-01-24 | 1993-09-21 | Cargill, Incorporated | Continuous process for manufacture of lactide polymers with controlled optical purity |
| US5142023A (en) * | 1992-01-24 | 1992-08-25 | Cargill, Incorporated | Continuous process for manufacture of lactide polymers with controlled optical purity |
| US5780051A (en) * | 1992-04-02 | 1998-07-14 | Dynagen, Inc. | Methods and articles of manufacture for nicotine cessation and monitoring nicotine use |
| DE4218268C2 (de) * | 1992-06-03 | 1997-01-16 | Boehringer Ingelheim Kg | Verfahren zur Reinigung bioresorbierbarer Polyester |
| US5922340A (en) * | 1992-09-10 | 1999-07-13 | Children's Medical Center Corporation | High load formulations and methods for providing prolonged local anesthesia |
| BR9305658A (pt) * | 1992-10-02 | 1996-11-26 | Cargill Inc | Papel tendo um polímero de lactideo estável em fusao e processo para sua produçao |
| US6005068A (en) | 1992-10-02 | 1999-12-21 | Cargill Incorporated | Melt-stable amorphous lactide polymer film and process for manufacture thereof |
| US5338822A (en) * | 1992-10-02 | 1994-08-16 | Cargill, Incorporated | Melt-stable lactide polymer composition and process for manufacture thereof |
| BR9305661A (pt) * | 1992-10-02 | 1996-11-26 | Cargill Inc | Pano de polímero de lactideo estável em fusao e processo para a sua fabricaçao |
| TW333456B (en) * | 1992-12-07 | 1998-06-11 | Takeda Pharm Ind Co Ltd | A pharmaceutical composition of sustained-release preparation the invention relates to a pharmaceutical composition of sustained-release preparation which comprises a physiologically active peptide. |
| JP3309502B2 (ja) * | 1993-07-12 | 2002-07-29 | 大日本インキ化学工業株式会社 | 生分解性ポリエステル系ポリマーの連続製造法 |
| DE69422053T2 (de) * | 1993-10-15 | 2000-06-29 | Fuller H B Licensing Financ | Biologisch abbaubare bzw. kompostierbare hot melt-klebstoffe, enthaltend polyester auf basis von milchsäure |
| AU706541B2 (en) | 1995-06-09 | 1999-06-17 | Euro-Celtique S.A. | Formulations and methods for providing prolonged local anesthesia |
| US5747060A (en) * | 1996-03-26 | 1998-05-05 | Euro-Celtique, S.A. | Prolonged local anesthesia with colchicine |
| EP0954301A4 (en) | 1996-06-24 | 2006-03-08 | Euro Celtique Sa | SAFE METHODS OF LOCAL ANESTHESIA |
| US6046187A (en) * | 1996-09-16 | 2000-04-04 | Children's Medical Center Corporation | Formulations and methods for providing prolonged local anesthesia |
| CA2219698C (en) | 1996-10-31 | 2007-09-04 | Takeda Chemical Industries, Ltd. | Sustained-release preparation |
| US6248345B1 (en) | 1997-07-02 | 2001-06-19 | Euro-Celtique, S.A. | Prolonged anesthesia in joints and body spaces |
| EP1310517B2 (en) * | 2000-08-07 | 2010-11-17 | Wako Pure Chemical Industries, Ltd. | Lactic acid polymer and process for producing the same |
| JP2005065771A (ja) * | 2003-08-20 | 2005-03-17 | Jms Co Ltd | 生体吸収性高分子の製造方法 |
| US20050227101A1 (en) * | 2004-04-12 | 2005-10-13 | Carpenter Brandon C | Wrapper for sandwiches and other products |
| DE602006000381T2 (de) * | 2005-04-28 | 2008-12-18 | Nipro Corp., Osaka | Bioabsorbierbare pharmazeutische Zusammensetzung enthaltend einen PLGA-Copolymer |
| US20100184891A1 (en) * | 2007-09-12 | 2010-07-22 | Kureha Corporation | Low melt viscosity polyglycolic acid, production process thereof, and use of low melt viscosity polyglycolic acid |
| WO2022163035A1 (ja) * | 2021-01-26 | 2022-08-04 | 株式会社カネカ | ポリエステル生産システム、ポリエステル生産方法、及びプログラム |
| LU502257B1 (en) | 2022-06-13 | 2023-12-13 | Univ Hamburg | Method for the depolymerization of a poly(alpha-hydroxy acid) |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297033A (en) * | 1963-10-31 | 1967-01-10 | American Cyanamid Co | Surgical sutures |
| DE1645629A1 (de) * | 1966-05-16 | 1970-10-22 | Wolfen Filmfab Veb | Verfahren zur Molekulargewichtsregelung bei der Herstellung von Polyestern durch Polymerisation von Glykolid |
| US3773919A (en) * | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| US3839297A (en) * | 1971-11-22 | 1974-10-01 | Ethicon Inc | Use of stannous octoate catalyst in the manufacture of l(-)lactide-glycolide copolymer sutures |
| DE2442387C3 (de) * | 1974-09-04 | 1981-09-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen hydrolytischen Aufspaltung von hydrolysierbaren Kunststoffabfällen |
| US4273920A (en) * | 1979-09-12 | 1981-06-16 | Eli Lilly And Company | Polymerization process and product |
| DE3176533D1 (en) * | 1980-10-20 | 1987-12-23 | American Cyanamid Co | Modification of polyglycolic acid to achieve variable in-vivo physical properties |
| IE52535B1 (en) * | 1981-02-16 | 1987-12-09 | Ici Plc | Continuous release pharmaceutical compositions |
| US4443430A (en) * | 1982-11-16 | 1984-04-17 | Ethicon, Inc. | Synthetic absorbable hemostatic agent |
| CA1256638A (en) * | 1984-07-06 | 1989-06-27 | Motoaki Tanaka | Polymer and its production |
-
1986
- 1986-04-18 GB GB868609537A patent/GB8609537D0/en active Pending
-
1987
- 1987-03-24 IE IE76687A patent/IE59961B1/en not_active IP Right Cessation
- 1987-03-25 ZA ZA872206A patent/ZA872206B/xx unknown
- 1987-03-27 IL IL82032A patent/IL82032A/xx not_active IP Right Cessation
- 1987-04-02 US US07/033,196 patent/US4789726A/en not_active Expired - Lifetime
- 1987-04-07 AU AU71156/87A patent/AU595594B2/en not_active Expired
- 1987-04-08 DK DK179987A patent/DK167195B1/da active IP Right Grant
- 1987-04-09 FI FI871564A patent/FI89505C/sv not_active IP Right Cessation
- 1987-04-13 EP EP87303220A patent/EP0244114B1/en not_active Expired - Lifetime
- 1987-04-13 DE DE8787303220T patent/DE3762421D1/de not_active Expired - Lifetime
- 1987-04-13 ES ES87303220T patent/ES2014474B3/es not_active Expired - Lifetime
- 1987-04-13 AT AT87303220T patent/ATE52268T1/de not_active IP Right Cessation
- 1987-04-15 PT PT84682A patent/PT84682B/pt unknown
- 1987-04-15 HU HU871654A patent/HU197032B/hu unknown
- 1987-04-15 NO NO871625A patent/NO169017C/no unknown
- 1987-04-16 NZ NZ220011A patent/NZ220011A/en unknown
- 1987-04-16 CA CA000534914A patent/CA1279148C/en not_active Expired - Lifetime
- 1987-04-17 JP JP62093413A patent/JP2553076B2/ja not_active Expired - Lifetime
-
1990
- 1990-04-26 GR GR89400171T patent/GR3001199T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2553076B2 (ja) | 1996-11-13 |
| IE870766L (en) | 1987-10-18 |
| US4789726A (en) | 1988-12-06 |
| PT84682B (pt) | 1989-12-29 |
| IL82032A0 (en) | 1987-10-20 |
| AU595594B2 (en) | 1990-04-05 |
| HU197032B (en) | 1989-02-28 |
| DK179987A (da) | 1987-10-19 |
| ES2014474B3 (es) | 1990-07-16 |
| EP0244114B1 (en) | 1990-04-25 |
| NZ220011A (en) | 1990-04-26 |
| EP0244114A1 (en) | 1987-11-04 |
| DK167195B1 (da) | 1993-09-13 |
| FI871564A0 (fi) | 1987-04-09 |
| NO871625D0 (no) | 1987-04-15 |
| NO169017B (no) | 1992-01-20 |
| DE3762421D1 (de) | 1990-05-31 |
| FI871564A (fi) | 1987-10-19 |
| JPS62252421A (ja) | 1987-11-04 |
| PT84682A (en) | 1987-05-01 |
| ATE52268T1 (de) | 1990-05-15 |
| GR3001199T3 (en) | 1992-06-30 |
| ZA872206B (en) | 1987-12-30 |
| IE59961B1 (en) | 1994-05-04 |
| NO169017C (no) | 1992-04-29 |
| CA1279148C (en) | 1991-01-15 |
| AU7115687A (en) | 1987-10-22 |
| DK179987D0 (da) | 1987-04-08 |
| NO871625L (no) | 1987-10-19 |
| FI89505C (sv) | 1993-10-11 |
| HUT44051A (en) | 1988-01-28 |
| GB8609537D0 (en) | 1986-05-21 |
| IL82032A (en) | 1990-12-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI89505B (fi) | Foerfarande foer framstaellning av polyestrar | |
| Zhou et al. | Synthesis and characterization of biodegradable low molecular weight aliphatic polyesters and their use in protein‐delivery systems | |
| AU2006271727B2 (en) | Resorbable polyether esters for producing medical implants | |
| EP1404738B1 (en) | Polyhydroxycarboxylic acid and its production process | |
| US4859763A (en) | Preparation process of dl-lactic acid-glycolic acid-copolymer | |
| US20060004183A1 (en) | Process for producing aliphatic polyester | |
| Triki et al. | Furan-based poly (esteramide) s by bulk copolycondensation | |
| US20060047088A1 (en) | High-molecular aliphatic polyester and process for producing the same | |
| Chen et al. | A novel biodegradable poly (p-dioxanone)-grafted poly (vinyl alcohol) copolymer with a controllable in vitro degradation | |
| JP3319553B2 (ja) | ポリ乳酸系樹脂組成物 | |
| JP3287425B2 (ja) | 水酸基末端をエステル封鎖したポリ乳酸およびその製造法 | |
| JP3796891B2 (ja) | ポリ乳酸組成物およびその製造方法ならびに該組成物の成形品 | |
| JP3747563B2 (ja) | ポリ乳酸組成物およびその製造方法ならびに該組成物の成形品 | |
| JP2606260B2 (ja) | ブロック共重合体 | |
| JP3144231B2 (ja) | 脂肪族ポリエステルおよび／またはその共重合体 | |
| JP3339600B2 (ja) | ポリ乳酸及び／又はその共重合体 | |
| JP3353853B2 (ja) | 実質的に全末端水酸基をエステル封鎖したポリ乳酸およびその製造法 | |
| JP3144416B2 (ja) | 脂肪族ポリエステルおよび／またはその共重合体 | |
| Lan et al. | Study on synthesis and mechanism of melt polymerization of L-lactic acid | |
| JP3287426B2 (ja) | 脂肪族ポリエステルの製造方法 | |
| JPH11116594A (ja) | スズ化合物、その製法、及びこれを用いたポリ（３−ヒドロキシ酪酸）類の製造方法 | |
| JPH03277628A (ja) | 脂肪族ポリエステルの低分子量化方法およびその成型方法 | |
| EP0764671A1 (en) | Process for producing poly(hydroxy carboxylic acid) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Patent granted |
Owner name: ASTRAZENECA UK LIMITED |
|
| MA | Patent expired |