CH616417A5 - Process for the preparation of asymmetrically substituted 1,4-dioxane-2,5-diones and polymers thereof, and the use of the polymers - Google Patents
Process for the preparation of asymmetrically substituted 1,4-dioxane-2,5-diones and polymers thereof, and the use of the polymers Download PDFInfo
- Publication number
- CH616417A5 CH616417A5 CH61375A CH61375A CH616417A5 CH 616417 A5 CH616417 A5 CH 616417A5 CH 61375 A CH61375 A CH 61375A CH 61375 A CH61375 A CH 61375A CH 616417 A5 CH616417 A5 CH 616417A5
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- Switzerland
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- polymer
- methyl
- acid
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- 229920000642 polymer Chemical class 0.000 title claims description 115
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical class O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title claims description 17
- 230000008569 process Effects 0.000 title claims description 11
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 52
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 38
- MVXNGTMKSZHHCO-UHFFFAOYSA-N 3-methyl-1,4-dioxane-2,5-dione Chemical compound CC1OC(=O)COC1=O MVXNGTMKSZHHCO-UHFFFAOYSA-N 0.000 claims description 29
- 238000006116 polymerization reaction Methods 0.000 claims description 26
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 16
- 239000000835 fiber Substances 0.000 claims description 16
- 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 15
- 229920000954 Polyglycolide Polymers 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 14
- 239000004310 lactic acid Substances 0.000 claims description 13
- 235000014655 lactic acid Nutrition 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 11
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
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- 229920000747 poly(lactic acid) Polymers 0.000 claims description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 6
- LLZIQIHXYWEQCA-UHFFFAOYSA-N 3,3-dimethyl-1,4-dioxane-2,5-dione Chemical compound CC1(C)OC(=O)COC1=O LLZIQIHXYWEQCA-UHFFFAOYSA-N 0.000 claims description 5
- 229910014033 C-OH Inorganic materials 0.000 claims description 5
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
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- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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- NIKVNJJACUGXFD-UHFFFAOYSA-N (2-chloroacetyl) 2-hydroxypropanoate Chemical compound CC(O)C(=O)OC(=O)CCl NIKVNJJACUGXFD-UHFFFAOYSA-N 0.000 claims 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- GZYXPXGNODDCBD-UHFFFAOYSA-N 3,3,6,6-tetramethyl-1,4-dioxane-2,5-dione Chemical compound CC1(C)OC(=O)C(C)(C)OC1=O GZYXPXGNODDCBD-UHFFFAOYSA-N 0.000 claims 1
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- VAIZVCMDJPBJCM-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-one;trihydrate Chemical compound O.O.O.FC(F)(F)C(=O)C(F)(F)F.FC(F)(F)C(=O)C(F)(F)F VAIZVCMDJPBJCM-UHFFFAOYSA-N 0.000 description 12
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- 239000007943 implant Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000004800 psychological effect Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 229920006268 silicone film Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000012414 sterilization procedure Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000003746 surface roughness Effects 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
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L17/00—Materials for surgical sutures or for ligaturing blood vessels ; Materials for prostheses or catheters
- A61L17/06—At least partially resorbable materials
- A61L17/10—At least partially resorbable materials containing macromolecular materials
- A61L17/105—Polyesters not covered by A61L17/12
-
- 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)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Surgery (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Materials For Medical Uses (AREA)
- Polyesters Or Polycarbonates (AREA)
- Biological Depolymerization Polymers (AREA)
- Dental Preparations (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43536574A | 1974-01-21 | 1974-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616417A5 true CH616417A5 (en) | 1980-03-31 |
Family
ID=23728099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH61375A CH616417A5 (en) | 1974-01-21 | 1975-01-20 | Process for the preparation of asymmetrically substituted 1,4-dioxane-2,5-diones and polymers thereof, and the use of the polymers |
Country Status (22)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56157422A (en) * | 1980-05-07 | 1981-12-04 | Mitsui Toatsu Chem Inc | Acetylated polyglycolic acid and preparation thereof |
| ES2030409T3 (es) * | 1986-10-24 | 1992-11-01 | Boehringer Ingelheim Kg | Procedimiento para preparar y purificar compuestos termolabiles . |
| EP0318567B1 (de) * | 1987-06-16 | 1992-03-18 | Boehringer Ingelheim Kg | Meso-lactid und verfahren zu seiner herstellung |
| EP0339882A1 (en) * | 1988-04-27 | 1989-11-02 | MITSUI TOATSU CHEMICALS, Inc. | Process for the production of lactide |
| DE4321355A1 (de) * | 1993-06-26 | 1995-01-05 | Basf Ag | Polylactid mit Langkettenverzweigungen |
| DE4440095A1 (de) * | 1994-11-10 | 1996-05-15 | Braun B Surgical Gmbh | Chirurgisches Nahtmaterial, seine Verwendung in der Chirurgie und Verfahren zu seiner Herstellung |
| ATE212062T1 (de) | 1996-02-08 | 2002-02-15 | Oekologische Technologie Und S | Verfahren zur herstellung von organischen aminiumlactaten und deren verwendung zur herstellung von dilactid |
| FR2873371B1 (fr) * | 2004-07-26 | 2008-07-04 | Sod Conseils Rech Applic | Nouvelle methode de synthese de 2,5 dioxane 1,4 diones |
| EP2018361A4 (en) * | 2006-05-15 | 2011-12-14 | Tyco Healthcare | HALOGENATED CYCLIC LACTONES AND POLYMERS COMPRISING SUCH LACTONES |
| ES2690971T3 (es) | 2011-08-23 | 2018-11-23 | Asana Biosciences, Llc | Compuestos pirimido-piridazinona y uso de los mismos |
| EP2812372B1 (en) | 2012-02-09 | 2018-09-26 | Novus International Inc. | Heteroatom containing cyclic dimers |
-
1974
- 1974-12-24 CA CA216,765A patent/CA1052046A/en not_active Expired
- 1974-12-31 IE IE2680/74A patent/IE40657B1/xx unknown
-
1975
- 1975-01-01 AR AR257269A patent/AR205454A1/es active
- 1975-01-02 ZA ZA00750038A patent/ZA7538B/xx unknown
- 1975-01-03 IN IN23/CAL/1975A patent/IN141151B/en unknown
- 1975-01-09 GB GB1003/75A patent/GB1494781A/en not_active Expired
- 1975-01-10 PH PH16698A patent/PH12680A/en unknown
- 1975-01-13 RO RO7581101A patent/RO70688A/ro unknown
- 1975-01-14 CS CS75253A patent/CS196258B2/cs unknown
- 1975-01-15 DE DE19752501448 patent/DE2501448A1/de not_active Withdrawn
- 1975-01-20 DK DK15275*BA patent/DK15275A/da not_active Application Discontinuation
- 1975-01-20 SE SE7500594A patent/SE7500594L/xx unknown
- 1975-01-20 IT IT47760/75A patent/IT1044114B/it active
- 1975-01-20 DD DD183736A patent/DD119259A5/xx unknown
- 1975-01-20 CH CH61375A patent/CH616417A5/de not_active IP Right Cessation
- 1975-01-20 AT AT39075A patent/AT339902B/de not_active IP Right Cessation
- 1975-01-20 PL PL1975177442A patent/PL101805B1/pl unknown
- 1975-01-20 HU HU75AE436A patent/HU173692B/hu unknown
- 1975-01-20 BE BE152494A patent/BE824535A/xx unknown
- 1975-01-21 JP JP50008413A patent/JPS50101367A/ja active Pending
- 1975-01-21 FR FR7501823A patent/FR2279745A1/fr active Granted
- 1975-01-21 NL NL7500689A patent/NL7500689A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA7538B (en) | 1976-01-28 |
| CA1052046A (en) | 1979-04-03 |
| IE40657B1 (en) | 1979-07-18 |
| SE7500594L (enrdf_load_stackoverflow) | 1975-07-22 |
| DD119259A5 (enrdf_load_stackoverflow) | 1976-04-12 |
| FR2279745A1 (fr) | 1976-02-20 |
| GB1494781A (en) | 1977-12-14 |
| BE824535A (fr) | 1975-07-22 |
| AT339902B (de) | 1977-11-10 |
| DE2501448A1 (de) | 1975-07-24 |
| IE40657L (en) | 1975-07-21 |
| AR205454A1 (es) | 1976-05-07 |
| IN141151B (enrdf_load_stackoverflow) | 1977-01-22 |
| RO70688A (ro) | 1982-05-10 |
| CS196258B2 (en) | 1980-03-31 |
| AU7708575A (en) | 1976-07-08 |
| HU173692B (hu) | 1979-07-28 |
| DK15275A (enrdf_load_stackoverflow) | 1975-09-15 |
| ATA39075A (de) | 1977-03-15 |
| PH12680A (en) | 1979-07-18 |
| IT1044114B (it) | 1980-03-20 |
| FR2279745B1 (enrdf_load_stackoverflow) | 1978-02-24 |
| JPS50101367A (enrdf_load_stackoverflow) | 1975-08-11 |
| PL101805B1 (pl) | 1979-02-28 |
| NL7500689A (nl) | 1975-07-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |