NO330434B1 - Fremgangsmate for fremstilling av polyestere som har intrakjede fri-syrefunksjoner - Google Patents
Fremgangsmate for fremstilling av polyestere som har intrakjede fri-syrefunksjoner Download PDFInfo
- Publication number
- NO330434B1 NO330434B1 NO20033783A NO20033783A NO330434B1 NO 330434 B1 NO330434 B1 NO 330434B1 NO 20033783 A NO20033783 A NO 20033783A NO 20033783 A NO20033783 A NO 20033783A NO 330434 B1 NO330434 B1 NO 330434B1
- Authority
- NO
- Norway
- Prior art keywords
- lactide
- acid
- lactic acid
- chain
- polyester
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 229920000728 polyester Polymers 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims abstract description 20
- -1 benzyl diester Chemical class 0.000 claims abstract description 20
- 239000003999 initiator Substances 0.000 claims abstract description 14
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000011975 tartaric acid Substances 0.000 claims abstract description 13
- 235000002906 tartaric acid Nutrition 0.000 claims abstract description 13
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims abstract description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 12
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 12
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 12
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims description 8
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- 238000010511 deprotection reaction Methods 0.000 claims description 7
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 7
- JJTUDXZGHPGLLC-ZXZARUISSA-N (3r,6s)-3,6-dimethyl-1,4-dioxane-2,5-dione Chemical compound C[C@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-ZXZARUISSA-N 0.000 claims description 6
- 229930182843 D-Lactic acid Natural products 0.000 claims description 6
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 claims description 6
- 229940022769 d- lactic acid Drugs 0.000 claims description 6
- 229960000448 lactic acid Drugs 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- VPVXHAANQNHFSF-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical compound O=C1COCCO1 VPVXHAANQNHFSF-UHFFFAOYSA-N 0.000 claims description 4
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical class O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims description 4
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- SJDLIJNQXLJBBE-UHFFFAOYSA-N 1,4-dioxepan-2-one Chemical compound O=C1COCCCO1 SJDLIJNQXLJBBE-UHFFFAOYSA-N 0.000 claims description 2
- AOLNDUQWRUPYGE-UHFFFAOYSA-N 1,4-dioxepan-5-one Chemical compound O=C1CCOCCO1 AOLNDUQWRUPYGE-UHFFFAOYSA-N 0.000 claims description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-M 3-hydroxybutyrate Chemical compound CC(O)CC([O-])=O WHBMMWSBFZVSSR-UHFFFAOYSA-M 0.000 claims description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N R3HBA Natural products CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 abstract description 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- HNERUQGVRKFROS-UHFFFAOYSA-N 2,3-dihydroxy-4-oxo-4-phenylmethoxybutanoic acid Chemical compound OC(=O)C(O)C(O)C(=O)OCC1=CC=CC=C1 HNERUQGVRKFROS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229920002988 biodegradable polymer Polymers 0.000 description 2
- 239000004621 biodegradable polymer Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical compound OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000008275 binding mechanism Effects 0.000 description 1
- 229920000229 biodegradable polyester Polymers 0.000 description 1
- 239000004622 biodegradable polyester Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- YYZUSRORWSJGET-UHFFFAOYSA-N ethyl octanoate Chemical compound CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/823—Preparation processes characterised by the catalyst used for the preparation of polylactones or polylactides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0102630A FR2821360B1 (fr) | 2001-02-27 | 2001-02-27 | Procede de preparation de polyesters avec des fonctions acides libres intracatenaires |
| PCT/FR2002/000655 WO2002068499A1 (fr) | 2001-02-27 | 2002-02-22 | Procede de preparation de polyesters avec des fonctions acides libres intracatenaires |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20033783D0 NO20033783D0 (no) | 2003-08-26 |
| NO20033783L NO20033783L (no) | 2003-08-26 |
| NO330434B1 true NO330434B1 (no) | 2011-04-11 |
Family
ID=8860480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20033783A NO330434B1 (no) | 2001-02-27 | 2003-08-26 | Fremgangsmate for fremstilling av polyestere som har intrakjede fri-syrefunksjoner |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7094862B2 (ja) |
| EP (1) | EP1366105B1 (ja) |
| JP (1) | JP4106271B2 (ja) |
| AT (1) | ATE302228T1 (ja) |
| CA (1) | CA2437520C (ja) |
| DE (1) | DE60205594T2 (ja) |
| DK (1) | DK1366105T3 (ja) |
| ES (1) | ES2246388T3 (ja) |
| FR (1) | FR2821360B1 (ja) |
| NO (1) | NO330434B1 (ja) |
| RU (1) | RU2282638C2 (ja) |
| WO (1) | WO2002068499A1 (ja) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1367080A1 (en) | 2002-05-29 | 2003-12-03 | Hycail B.V. | Hyperbranched poly(hydroxycarboxylic acid) polymers |
| US9149558B2 (en) * | 2005-05-19 | 2015-10-06 | Ethicon, Inc. | Antimicrobial polymer compositions and the use thereof |
| US9180229B2 (en) * | 2005-05-19 | 2015-11-10 | Ethicon, Inc. | Antimicrobial polymer compositions and the use thereof |
| US7794495B2 (en) * | 2006-07-17 | 2010-09-14 | Advanced Cardiovascular Systems, Inc. | Controlled degradation of stents |
| MY156587A (en) * | 2008-07-31 | 2016-03-15 | Purac Biochem Bv | Process for the continuous production of polyesters |
| US8501875B2 (en) | 2010-10-28 | 2013-08-06 | Covidien Lp | Surface induced ring-opening polymerization and medical devices formed therefrom |
| CN103442776B (zh) * | 2011-02-18 | 2015-09-02 | 苏舍化学技术有限公司 | 聚羟基-羧酸的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0000732A3 (en) * | 1996-04-23 | 2000-11-28 | Ipsen Mfg Ireland Ltd | Acidic polylactic polymers |
| US6867181B1 (en) * | 1997-06-02 | 2005-03-15 | Societe De Conseils De Recherches Et D'applications Scientifiques, S.A.S. | Ionic molecular conjugates of biodegradable polyesters and bioactive polypeptides |
| ES2234325T3 (es) * | 1998-12-15 | 2005-06-16 | Takeda Pharmaceutical Company Limited | Procedimiento para producir poliesteres biodegradables. |
-
2001
- 2001-02-27 FR FR0102630A patent/FR2821360B1/fr not_active Expired - Fee Related
-
2002
- 2002-02-22 EP EP02704876A patent/EP1366105B1/fr not_active Expired - Lifetime
- 2002-02-22 AT AT02704876T patent/ATE302228T1/de active
- 2002-02-22 WO PCT/FR2002/000655 patent/WO2002068499A1/fr active IP Right Grant
- 2002-02-22 JP JP2002568007A patent/JP4106271B2/ja not_active Expired - Fee Related
- 2002-02-22 ES ES02704876T patent/ES2246388T3/es not_active Expired - Lifetime
- 2002-02-22 DK DK02704876T patent/DK1366105T3/da active
- 2002-02-22 RU RU2003128961/04A patent/RU2282638C2/ru not_active IP Right Cessation
- 2002-02-22 US US10/469,444 patent/US7094862B2/en not_active Expired - Fee Related
- 2002-02-22 DE DE60205594T patent/DE60205594T2/de not_active Expired - Lifetime
- 2002-02-22 CA CA2437520A patent/CA2437520C/fr not_active Expired - Fee Related
-
2003
- 2003-08-26 NO NO20033783A patent/NO330434B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1366105B1 (fr) | 2005-08-17 |
| EP1366105A1 (fr) | 2003-12-03 |
| FR2821360A1 (fr) | 2002-08-30 |
| RU2282638C2 (ru) | 2006-08-27 |
| ATE302228T1 (de) | 2005-09-15 |
| RU2003128961A (ru) | 2005-03-10 |
| NO20033783D0 (no) | 2003-08-26 |
| CA2437520C (fr) | 2011-08-30 |
| JP2004533494A (ja) | 2004-11-04 |
| CA2437520A1 (fr) | 2002-09-06 |
| JP4106271B2 (ja) | 2008-06-25 |
| US20040127676A1 (en) | 2004-07-01 |
| ES2246388T3 (es) | 2006-02-16 |
| DE60205594D1 (de) | 2005-09-22 |
| WO2002068499A1 (fr) | 2002-09-06 |
| NO20033783L (no) | 2003-08-26 |
| DK1366105T3 (da) | 2005-12-27 |
| US7094862B2 (en) | 2006-08-22 |
| DE60205594T2 (de) | 2006-05-18 |
| FR2821360B1 (fr) | 2003-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |