NO309530B1 - Kontinuerlig fremgangsmåte til fremstilling av laktidpolymerer med forbedrede rensemetoder - Google Patents
Kontinuerlig fremgangsmåte til fremstilling av laktidpolymerer med forbedrede rensemetoder Download PDFInfo
- Publication number
- NO309530B1 NO309530B1 NO942728A NO942728A NO309530B1 NO 309530 B1 NO309530 B1 NO 309530B1 NO 942728 A NO942728 A NO 942728A NO 942728 A NO942728 A NO 942728A NO 309530 B1 NO309530 B1 NO 309530B1
- Authority
- NO
- Norway
- Prior art keywords
- lactide
- lactic acid
- polylactic acid
- stream
- stated
- Prior art date
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- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 title claims abstract description 427
- 238000000034 method Methods 0.000 title claims abstract description 130
- 229920000642 polymer Polymers 0.000 title claims abstract description 83
- 238000000746 purification Methods 0.000 title claims description 27
- 238000010924 continuous production Methods 0.000 title description 6
- 229920000747 poly(lactic acid) Polymers 0.000 claims abstract description 166
- 238000004821 distillation Methods 0.000 claims abstract description 145
- 239000000203 mixture Substances 0.000 claims abstract description 111
- 238000009835 boiling Methods 0.000 claims abstract description 74
- 230000008569 process Effects 0.000 claims abstract description 46
- 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 22
- 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 abstract description 16
- 238000001953 recrystallisation Methods 0.000 claims abstract description 10
- 238000000638 solvent extraction Methods 0.000 claims abstract description 5
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 523
- 235000014655 lactic acid Nutrition 0.000 claims description 262
- 239000004310 lactic acid Substances 0.000 claims description 260
- 239000003054 catalyst Substances 0.000 claims description 188
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- 150000002148 esters Chemical class 0.000 claims description 98
- 239000000463 material Substances 0.000 claims description 63
- 238000006243 chemical reaction Methods 0.000 claims description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- 238000006116 polymerization reaction Methods 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 51
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 46
- 239000012535 impurity Substances 0.000 claims description 40
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 claims description 31
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims description 31
- 229940057867 methyl lactate Drugs 0.000 claims description 31
- 238000006482 condensation reaction Methods 0.000 claims description 30
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims description 9
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 238000004140 cleaning Methods 0.000 claims description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000010926 purge Methods 0.000 claims description 6
- 229910021645 metal ion Inorganic materials 0.000 claims description 5
- WBPAQKQBUKYCJS-UHFFFAOYSA-N 2-methylpropyl 2-hydroxypropanoate Chemical compound CC(C)COC(=O)C(C)O WBPAQKQBUKYCJS-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- KIWATKANDHUUOB-UHFFFAOYSA-N propan-2-yl 2-hydroxypropanoate Chemical compound CC(C)OC(=O)C(C)O KIWATKANDHUUOB-UHFFFAOYSA-N 0.000 claims description 4
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 claims description 4
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- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 22
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- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(II) oxide Inorganic materials [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 16
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
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- 229930182843 D-Lactic acid Natural products 0.000 description 7
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
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- 238000004817 gas chromatography Methods 0.000 description 7
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- 229940094938 stannous 2-ethylhexanoate Drugs 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000004457 water analysis Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229960000314 zinc acetate Drugs 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
- C08G63/78—Preparation processes
-
- 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
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/825,059 US5142023A (en) | 1992-01-24 | 1992-01-24 | Continuous process for manufacture of lactide polymers with controlled optical purity |
US07/926,901 US5258488A (en) | 1992-01-24 | 1992-08-07 | Continuous process for manufacture of lactide polymers with controlled optical purity |
US07/927,149 US5247058A (en) | 1992-01-24 | 1992-08-07 | Continuous process for manufacture of lactide polymers with controlled optical purity |
US07/935,566 US5247059A (en) | 1992-01-24 | 1992-08-24 | Continuous process for the manufacture of a purified lactide from esters of lactic acid |
US07/935,059 US5274073A (en) | 1992-01-24 | 1992-08-24 | Continuous process for manufacture of a purified lactide |
PCT/US1993/000568 WO1993015127A1 (fr) | 1992-01-24 | 1993-01-22 | Procede continu de fabrication de lactide et de polymeres de lactide |
Publications (3)
Publication Number | Publication Date |
---|---|
NO942728D0 NO942728D0 (no) | 1994-07-21 |
NO942728L NO942728L (no) | 1994-09-23 |
NO309530B1 true NO309530B1 (no) | 2001-02-12 |
Family
ID=27542241
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO942728A NO309530B1 (no) | 1992-01-24 | 1994-07-21 | Kontinuerlig fremgangsmåte til fremstilling av laktidpolymerer med forbedrede rensemetoder |
Country Status (14)
Country | Link |
---|---|
EP (2) | EP0623153A1 (fr) |
JP (1) | JP3258324B2 (fr) |
KR (1) | KR100261850B1 (fr) |
AT (1) | ATE466897T1 (fr) |
AU (1) | AU677174B2 (fr) |
BR (1) | BR9305788A (fr) |
CA (1) | CA2128509C (fr) |
DE (1) | DE69334330D1 (fr) |
ES (1) | ES2345307T3 (fr) |
FI (1) | FI113661B (fr) |
MX (1) | MX9300333A (fr) |
NO (1) | NO309530B1 (fr) |
NZ (1) | NZ249033A (fr) |
WO (1) | WO1993015127A1 (fr) |
Families Citing this family (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6326458B1 (en) * | 1992-01-24 | 2001-12-04 | Cargill, Inc. | Continuous process for the manufacture of lactide and lactide polymers |
US5521278A (en) * | 1994-08-18 | 1996-05-28 | Ecological Chemical Products | Integrated process for the manufacture of lactide |
JP3301311B2 (ja) * | 1996-05-24 | 2002-07-15 | 株式会社神戸製鋼所 | 2−ヒドロキシカルボン酸オリゴマーの連続製造方法 |
JPH10109983A (ja) * | 1996-10-04 | 1998-04-28 | Mitsubishi Gas Chem Co Inc | 環状エステルの製造方法および精製方法 |
JP4284709B2 (ja) * | 1996-12-25 | 2009-06-24 | トヨタ自動車株式会社 | 乳酸系副産物の再生利用法 |
DE60031897T2 (de) | 1999-06-18 | 2007-09-06 | Toray Industries, Inc. | Polymilchsäureharz, damit erhaltene Textilerzeugnisse und Verfahren zur Herstellung derselben |
FR2802923B1 (fr) | 1999-12-28 | 2002-03-08 | Roquette Freres | Procede de preparation d'une composition d'ester d'acide lactique et son utilisation en tant que solvant |
EP1357119B1 (fr) * | 2001-01-31 | 2011-05-11 | Toyota Jidosha Kabushiki Kaisha | Procede de production de lactide et procede de production d'acide polylactique partir d'acide lactique ferment |
BE1015060A3 (fr) * | 2002-08-06 | 2004-09-07 | Brussels Biotech Nv Sa | Procede de production de polylactide au depart d'une solution d'acide lactique ou d'un de ses derives. |
DE60320282T2 (de) * | 2002-10-08 | 2009-07-16 | Kureha Corp. | Verfahren zur herstellung von aliphatischem polyester |
US7829507B2 (en) | 2003-09-17 | 2010-11-09 | Halliburton Energy Services Inc. | Subterranean treatment fluids comprising a degradable bridging agent and methods of treating subterranean formations |
US7674753B2 (en) | 2003-09-17 | 2010-03-09 | Halliburton Energy Services, Inc. | Treatment fluids and methods of forming degradable filter cakes comprising aliphatic polyester and their use in subterranean formations |
US7833944B2 (en) | 2003-09-17 | 2010-11-16 | Halliburton Energy Services, Inc. | Methods and compositions using crosslinked aliphatic polyesters in well bore applications |
US8030249B2 (en) | 2005-01-28 | 2011-10-04 | Halliburton Energy Services, Inc. | Methods and compositions relating to the hydrolysis of water-hydrolysable materials |
US20060169182A1 (en) | 2005-01-28 | 2006-08-03 | Halliburton Energy Services, Inc. | Methods and compositions relating to the hydrolysis of water-hydrolysable materials |
US7662753B2 (en) | 2005-05-12 | 2010-02-16 | Halliburton Energy Services, Inc. | Degradable surfactants and methods for use |
US7318474B2 (en) | 2005-07-11 | 2008-01-15 | Halliburton Energy Services, Inc. | Methods and compositions for controlling formation fines and reducing proppant flow-back |
US8329621B2 (en) | 2006-07-25 | 2012-12-11 | Halliburton Energy Services, Inc. | Degradable particulates and associated methods |
US7686080B2 (en) | 2006-11-09 | 2010-03-30 | Halliburton Energy Services, Inc. | Acid-generating fluid loss control additives and associated methods |
NL2000454C1 (nl) | 2006-11-28 | 2008-01-02 | Purac Biochem Bv | Stabiele lactidedeeltjes. |
US20080146822A1 (en) | 2006-11-28 | 2008-06-19 | Purac Biochem B.V. | Stable lactide particles |
EP2031009A1 (fr) * | 2007-09-03 | 2009-03-04 | Uhde Inventa-Fischer GmbH | Dispositif de nettoyage destiné à la séparation de dilactide de mélanges de matières, dispositif de polymérisation, procédé de séparation de dilactide de mélanges de matières ainsi qu'utilisation |
JP4427571B2 (ja) | 2007-11-07 | 2010-03-10 | 株式会社日立プラントテクノロジー | ポリマー合成に関する装置および方法 |
AT506038B1 (de) | 2007-11-14 | 2015-02-15 | Jungbunzlauer Austria Ag | Verfahren zur herstellung zyklischer diester von l-, d- und d,l-milchsäure |
US8006760B2 (en) * | 2008-04-10 | 2011-08-30 | Halliburton Energy Services, Inc. | Clean fluid systems for partial monolayer fracturing |
AT506768B1 (de) | 2008-04-16 | 2013-10-15 | Jungbunzlauer Austria Ag | Verfahren zur reinigung zyklischer diester der l- bzw. d-milchsäure |
US7906464B2 (en) | 2008-05-13 | 2011-03-15 | Halliburton Energy Services, Inc. | Compositions and methods for the removal of oil-based filtercakes |
KR101012483B1 (ko) * | 2008-07-08 | 2011-02-09 | 김용환 | 효소 전환반응을 이용한 광학순수형 락티드 제조방법 및광학순수형 유산 또는 알킬 락테이트의 분리방법 |
JP5077170B2 (ja) | 2008-09-22 | 2012-11-21 | 株式会社日立プラントテクノロジー | ポリヒドロキシカルボン酸の製造方法 |
US7833943B2 (en) | 2008-09-26 | 2010-11-16 | Halliburton Energy Services Inc. | Microemulsifiers and methods of making and using same |
CN102439001B (zh) * | 2009-03-13 | 2014-09-17 | 自然工作有限责任公司 | 由内消旋-丙交酯流回收乳酸值 |
US8082992B2 (en) | 2009-07-13 | 2011-12-27 | Halliburton Energy Services, Inc. | Methods of fluid-controlled geometry stimulation |
AU2009352300B2 (en) * | 2009-09-14 | 2014-01-23 | Joseph Daniel Cook | Method for wet flue gas desulfurization |
CN101696203B (zh) * | 2009-10-26 | 2013-02-06 | 江苏科技大学 | 从粗l-丙交酯连续精制l-丙交酯的方法 |
BRPI1004962A2 (pt) * | 2010-08-20 | 2012-05-29 | Companhia Refinadora Da Amazonia | processo de produção de poli (ácido lático ) e reatores para utilização no referido processo |
JP2012097224A (ja) * | 2010-11-04 | 2012-05-24 | Hitachi Plant Technologies Ltd | ポリヒドロキシカルボン酸の製造装置および製造方法 |
EP2559725B1 (fr) | 2011-08-19 | 2024-05-08 | Uhde Inventa-Fischer GmbH | Procédé et dispositif de récupération de lactide à partir de polylactide ou de polylactile |
ES2536294T3 (es) | 2012-10-26 | 2015-05-22 | Uhde Inventa-Fischer Gmbh | Procedimiento para preparar diésteres cíclicos, especialmente dilactida |
KR101434462B1 (ko) * | 2012-12-26 | 2014-08-26 | 한국화학연구원 | 락타이드의 회분식 증류정제장치 및 이를 이용한 락타이드의 증류정제방법 |
EP2876124B1 (fr) * | 2013-11-20 | 2019-01-09 | Uhde Inventa-Fischer GmbH | Procédé et dispositif de fabrication d'un mélange d'acide polylactique et mélange d'acide polylactique |
WO2015086613A1 (fr) * | 2013-12-10 | 2015-06-18 | Futerro S.A. | Procédé perfectionné de production de polylactide |
EP3056490A1 (fr) * | 2015-02-13 | 2016-08-17 | PURAC Biochem BV | Procédé de fabrication de lactide |
EP3288930B1 (fr) * | 2015-04-30 | 2021-04-21 | PURAC Biochem BV | Procédé et dispositif pour fabriquer un lactide |
KR101780779B1 (ko) | 2015-09-24 | 2017-09-21 | 롯데케미칼 주식회사 | 고순도 락타이드의 제조 방법 |
KR101704563B1 (ko) | 2015-10-12 | 2017-02-08 | 한국화학연구원 | 락타이드 정제공정을 이용한 락타이드 제조방법 및 제조장치 |
US10562877B2 (en) * | 2016-06-20 | 2020-02-18 | Total Research & Technology Feluy | Single step lactide production process with hydrolysis of oligomers and catalyst by recovered water |
EP3406605B1 (fr) * | 2017-05-22 | 2022-04-20 | NatureWorks LLC | Procedes de production de lactide avec recristallisation et recyclage de meso-lactide |
CN110652946B (zh) * | 2019-09-24 | 2021-11-09 | 安徽神剑新材料股份有限公司 | 一种聚酯树脂生产过程中顶温控制系统及方法 |
CN116635376A (zh) * | 2020-12-24 | 2023-08-22 | 聚晟(新加坡)私人有限公司 | 丙交酯的生产工艺 |
JP2024518184A (ja) * | 2021-02-22 | 2024-04-25 | 聚晟(新加坡)私人有限公司 | ラクチドを製造する方法及び装置 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1995970A (en) * | 1931-04-04 | 1935-03-26 | Du Pont | Polymeric lactide resin |
DE3708915C2 (de) * | 1987-03-19 | 1996-04-04 | Boehringer Ingelheim Kg | Verfahren zur Herstellung von Lactid |
EP0261572A1 (fr) * | 1986-09-20 | 1988-03-30 | Boehringer Ingelheim Kg | Procédé de production de lactide |
ES2052551T3 (es) * | 1986-12-19 | 1994-07-16 | Akzo Nv | Metodo para preparar poli(acido lactico) o copolimeros de poli(acido lactico) por polimeracion de la lactida. |
DE3869343D1 (de) * | 1987-06-16 | 1992-04-23 | Boehringer Ingelheim Kg | Meso-lactid und verfahren zu seiner herstellung. |
NL8702563A (nl) | 1987-10-28 | 1989-05-16 | Cca Biochem B V | Polymeer lactide, werkwijze voor het bereiden van een dergelijk polymeer lactide, alsmede een samenstelling, die een dergelijk polymeer lactide bevat. |
-
1993
- 1993-01-22 EP EP93903632A patent/EP0623153A1/fr not_active Ceased
- 1993-01-22 KR KR1019940702555A patent/KR100261850B1/ko not_active IP Right Cessation
- 1993-01-22 MX MX9300333A patent/MX9300333A/es unknown
- 1993-01-22 AU AU34821/93A patent/AU677174B2/en not_active Ceased
- 1993-01-22 AT AT98203427T patent/ATE466897T1/de not_active IP Right Cessation
- 1993-01-22 CA CA002128509A patent/CA2128509C/fr not_active Expired - Fee Related
- 1993-01-22 ES ES98203427T patent/ES2345307T3/es not_active Expired - Lifetime
- 1993-01-22 EP EP98203427A patent/EP0893462B1/fr not_active Expired - Lifetime
- 1993-01-22 WO PCT/US1993/000568 patent/WO1993015127A1/fr active IP Right Grant
- 1993-01-22 DE DE69334330T patent/DE69334330D1/de not_active Expired - Lifetime
- 1993-01-22 NZ NZ249033A patent/NZ249033A/en not_active IP Right Cessation
- 1993-01-22 JP JP51333593A patent/JP3258324B2/ja not_active Expired - Fee Related
- 1993-01-22 BR BR9305788A patent/BR9305788A/pt not_active IP Right Cessation
-
1994
- 1994-07-21 NO NO942728A patent/NO309530B1/no not_active IP Right Cessation
- 1994-07-22 FI FI943487A patent/FI113661B/fi not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
FI113661B (fi) | 2004-05-31 |
FI943487A (fi) | 1994-09-21 |
CA2128509A1 (fr) | 1993-08-05 |
BR9305788A (pt) | 1997-02-18 |
EP0623153A1 (fr) | 1994-11-09 |
AU677174B2 (en) | 1997-04-17 |
CA2128509C (fr) | 2006-09-19 |
NO942728D0 (no) | 1994-07-21 |
KR100261850B1 (ko) | 2000-08-01 |
FI943487A0 (fi) | 1994-07-22 |
NO942728L (no) | 1994-09-23 |
AU3482193A (en) | 1993-09-01 |
ATE466897T1 (de) | 2010-05-15 |
EP0893462A3 (fr) | 1999-10-20 |
MX9300333A (es) | 1993-07-01 |
EP0893462A2 (fr) | 1999-01-27 |
DE69334330D1 (de) | 2010-06-17 |
WO1993015127A1 (fr) | 1993-08-05 |
ES2345307T3 (es) | 2010-09-20 |
EP0893462B1 (fr) | 2010-05-05 |
JPH07503490A (ja) | 1995-04-13 |
NZ249033A (en) | 1996-05-28 |
JP3258324B2 (ja) | 2002-02-18 |
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Legal Events
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MM1K | Lapsed by not paying the annual fees |