CA2472648C - Process for preparing reabsorbable polyesters by mass polymerisation - Google Patents
Process for preparing reabsorbable polyesters by mass polymerisation Download PDFInfo
- Publication number
- CA2472648C CA2472648C CA2472648A CA2472648A CA2472648C CA 2472648 C CA2472648 C CA 2472648C CA 2472648 A CA2472648 A CA 2472648A CA 2472648 A CA2472648 A CA 2472648A CA 2472648 C CA2472648 C CA 2472648C
- Authority
- CA
- Canada
- Prior art keywords
- lactide
- process according
- reabsorbable
- polyester
- containers
- 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 - Lifetime
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- 239000011541 reaction mixture Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims description 39
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 27
- -1 poly(L-lactide) Polymers 0.000 claims description 27
- 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 25
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims description 18
- 229920003023 plastic Polymers 0.000 claims description 18
- 239000004033 plastic Substances 0.000 claims description 18
- 239000004743 Polypropylene Substances 0.000 claims description 17
- 229920001155 polypropylene Polymers 0.000 claims description 17
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims description 15
- 229920001577 copolymer Polymers 0.000 claims description 11
- 229920001432 poly(L-lactide) Polymers 0.000 claims description 5
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 2
- 229920000954 Polyglycolide Polymers 0.000 claims description 2
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 2
- 229920001897 terpolymer Polymers 0.000 claims description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 2
- 238000012662 bulk polymerization Methods 0.000 claims 1
- 229920002313 fluoropolymer Polymers 0.000 claims 1
- 229920000098 polyolefin Polymers 0.000 claims 1
- 239000007943 implant Substances 0.000 abstract description 3
- 239000000178 monomer Substances 0.000 description 27
- 239000003054 catalyst Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 13
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 9
- 239000000155 melt Substances 0.000 description 8
- 230000004927 fusion Effects 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- 229920001634 Copolyester Polymers 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 235000014655 lactic acid Nutrition 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 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 description 4
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 4
- 239000004310 lactic acid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 101100425646 Caenorhabditis elegans tmc-1 gene Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XZZXKVYTWCYOQX-UHFFFAOYSA-J octanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O XZZXKVYTWCYOQX-UHFFFAOYSA-J 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003752 zinc compounds Chemical class 0.000 description 2
- 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 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000012568 clinical material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000010512 small scale reaction Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 238000004448 titration Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000008096 xylene 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
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
-
- 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
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)
- Materials For Medical Uses (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10200738A DE10200738A1 (de) | 2002-01-11 | 2002-01-11 | Verfahren zur Herstellung von resorbierbaren Polyestern durch Massepolymerisation |
| DE10200738.1 | 2002-01-11 | ||
| PCT/EP2003/000096 WO2003057756A1 (de) | 2002-01-11 | 2003-01-08 | Verfahren zur herstellung von resorbierbaren polyestern durch massepolymerisation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2472648A1 CA2472648A1 (en) | 2003-07-17 |
| CA2472648C true CA2472648C (en) | 2010-12-14 |
Family
ID=7711853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2472648A Expired - Lifetime CA2472648C (en) | 2002-01-11 | 2003-01-08 | Process for preparing reabsorbable polyesters by mass polymerisation |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1468035B1 (https=) |
| JP (1) | JP4975953B2 (https=) |
| AR (1) | AR038286A1 (https=) |
| AT (1) | ATE299156T1 (https=) |
| AU (1) | AU2003206699A1 (https=) |
| CA (1) | CA2472648C (https=) |
| DE (2) | DE10200738A1 (https=) |
| ES (1) | ES2244919T3 (https=) |
| PE (1) | PE20030842A1 (https=) |
| TW (1) | TW200302838A (https=) |
| UY (1) | UY27611A1 (https=) |
| WO (1) | WO2003057756A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7842261B2 (en) * | 2005-04-21 | 2010-11-30 | Purac Biochem Bv | Process for preparing resorbable polyesters by bulk polymerization |
| DE102007036101A1 (de) | 2007-08-01 | 2009-02-05 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue glycolidreiche Copolymere |
| EP2030679A1 (de) * | 2007-09-03 | 2009-03-04 | Uhde Inventa-Fischer GmbH | Polymerisationsreaktor, Polymerisationsvorrichtung, Verfahren zur Herstellung von bioabbaubarem Polyester sowie Verwendungen |
| WO2014108191A1 (en) | 2013-01-10 | 2014-07-17 | Evonik Industries Ag | Electronic device unit comprising a polymer coating |
| EP3039058B1 (en) | 2013-08-29 | 2024-10-23 | Evonik Operations GmbH | Process for preparing a bio-resorbable polyester in the form of a powder |
| CN107075134B (zh) | 2014-11-14 | 2021-03-09 | 赢创运营有限公司 | 制备微粒形式的生物可再吸收聚酯的方法 |
| US10322169B2 (en) | 2015-06-10 | 2019-06-18 | Evonik Roehm Gmbh | Process for preparing a powder comprising a human coagulation factor protein and a lactic acid polymer |
| EP3790534B1 (en) | 2018-05-08 | 2023-08-30 | Evonik Operations GmbH | Nanoparticle comprising a bio-resorbable polyester, a hydrophilic polymer and an acylated human lactoferrin-derived peptide |
| KR102884866B1 (ko) | 2018-11-27 | 2025-11-13 | 에보니크 오퍼레이션즈 게엠베하 | 벌크 중합에 의한 과립 또는 분말로서의 재흡수성 폴리에스테르의 제조 방법 |
| EP4312977A1 (en) | 2021-04-01 | 2024-02-07 | Biogen MA Inc. | Nucleic acid delivery to the central nervous system |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4379138A (en) * | 1981-12-28 | 1983-04-05 | Research Triangle Institute | Biodegradable polymers of lactones |
| US4643734A (en) * | 1983-05-05 | 1987-02-17 | Hexcel Corporation | Lactide/caprolactone polymer, method of making the same, composites thereof, and prostheses produced therefrom |
| EP0661325B1 (en) * | 1993-12-28 | 2001-10-10 | Dainippon Ink And Chemicals, Inc. | Continuously production process for lactide copolymer |
| JPH10316745A (ja) * | 1997-05-19 | 1998-12-02 | Tokuyama Corp | ポリ（ｐ−ジオキサノン）の製造方法 |
| WO2003006526A1 (en) * | 2001-07-10 | 2003-01-23 | Kureha Chemical Industry Company, Limited | Polyester production process and reactor apparatus |
-
2002
- 2002-01-11 DE DE10200738A patent/DE10200738A1/de not_active Ceased
-
2003
- 2003-01-07 UY UY27611A patent/UY27611A1/es not_active Application Discontinuation
- 2003-01-08 DE DE50300729T patent/DE50300729D1/de not_active Expired - Lifetime
- 2003-01-08 WO PCT/EP2003/000096 patent/WO2003057756A1/de not_active Ceased
- 2003-01-08 AT AT03704361T patent/ATE299156T1/de active
- 2003-01-08 AU AU2003206699A patent/AU2003206699A1/en not_active Abandoned
- 2003-01-08 ES ES03704361T patent/ES2244919T3/es not_active Expired - Lifetime
- 2003-01-08 EP EP03704361A patent/EP1468035B1/de not_active Expired - Lifetime
- 2003-01-08 JP JP2003558067A patent/JP4975953B2/ja not_active Expired - Lifetime
- 2003-01-08 CA CA2472648A patent/CA2472648C/en not_active Expired - Lifetime
- 2003-01-09 TW TW092100409A patent/TW200302838A/zh unknown
- 2003-01-09 PE PE2003000034A patent/PE20030842A1/es not_active Application Discontinuation
- 2003-01-10 AR ARP030100057A patent/AR038286A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| UY27611A1 (es) | 2003-08-29 |
| WO2003057756A1 (de) | 2003-07-17 |
| PE20030842A1 (es) | 2003-11-12 |
| JP2005514482A (ja) | 2005-05-19 |
| CA2472648A1 (en) | 2003-07-17 |
| EP1468035A1 (de) | 2004-10-20 |
| DE50300729D1 (de) | 2005-08-11 |
| JP4975953B2 (ja) | 2012-07-11 |
| AR038286A1 (es) | 2005-01-12 |
| ATE299156T1 (de) | 2005-07-15 |
| DE10200738A1 (de) | 2003-08-07 |
| ES2244919T3 (es) | 2005-12-16 |
| EP1468035B1 (de) | 2005-07-06 |
| TW200302838A (en) | 2003-08-16 |
| AU2003206699A1 (en) | 2003-07-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20230109 |