GB1040168A - High molecular weight polylactides and a process for their preparation - Google Patents

High molecular weight polylactides and a process for their preparation

Info

Publication number
GB1040168A
GB1040168A GB4477064A GB4477064A GB1040168A GB 1040168 A GB1040168 A GB 1040168A GB 4477064 A GB4477064 A GB 4477064A GB 4477064 A GB4477064 A GB 4477064A GB 1040168 A GB1040168 A GB 1040168A
Authority
GB
United Kingdom
Prior art keywords
lactide
hydroxy
group
glycolide
meso
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
Application number
GB4477064A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB1040168A publication Critical patent/GB1040168A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • A61L17/12—Homopolymers or copolymers of glycolic acid or lactic acid
    • 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

Abstract

The invention comprises a polylactide of the formula <FORM:1040168/C3/1> where M is a divalent metal of Group II of the Periodic Table, R1 and R2 are hydrocarbon residues of 1-12 carbon atoms and d1+d2 is the degree of polymerization, which is such that the inherent viscosity is at least 0.4. It is prepared by reacting a lactide <FORM:1040168/C3/2> of at least 90% purity with respect to hydroxy-containing compounds, with a compound of the formula MRX, where R is a 1-12 carbon atom hydrocarbon group and X is a similar group or a hydroxy, alkoxy, aryloxy, or acyloxy group, under anhydrous conditions at 20 DEG to 200 DEG C. The lactide is molten, or an inert solvent may be used, e.g. benzene, toluene, n-decane, or tetrahydronaphthalene. The compound MRX may be used in an amount of 0.001 to 1 weight per cent of the lactide. The lactide may be L(-) or D(+) or inactive, or a mixture, and may be copolymerized with other cyclic esters containing 6-8 carbon atoms in the ring, e.g. glycolide, tetramethylglycolide, sym-diethylglycolide, diphenylglycolide, 2-hydroxy-4,6,6-trimethylpeptanoic lactide, d -valerolactone, trimethylene carbonate, ethylene oxalate, propylene oxalate and disalicylide. In Examples, L(-) lactide (containing 10% meso-lactide in Example 2) or meso-lactide (in Example 6) or a 5: 1 mixture of L(-) lactide and glycolide (Example 8) are polymerized with diethylzinc or dibutylzinc or diethylmagnesium, in the molten state or in hydrocarbon solution.
GB4477064A 1963-11-08 1964-11-03 High molecular weight polylactides and a process for their preparation Expired GB1040168A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US32249463A 1963-11-08 1963-11-08

Publications (1)

Publication Number Publication Date
GB1040168A true GB1040168A (en) 1966-08-24

Family

ID=23255138

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4477064A Expired GB1040168A (en) 1963-11-08 1964-11-03 High molecular weight polylactides and a process for their preparation

Country Status (3)

Country Link
DE (1) DE1595085C3 (en)
GB (1) GB1040168A (en)
IT (1) IT998002B (en)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5142023A (en) * 1992-01-24 1992-08-25 Cargill, Incorporated Continuous process for manufacture of lactide polymers with controlled optical purity
US5225129A (en) * 1990-07-19 1993-07-06 Dsm N.V. Method for the manufacture of polymer products from cyclic esters
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
US5258488A (en) * 1992-01-24 1993-11-02 Cargill, Incorporated Continuous process for manufacture of lactide polymers with controlled optical purity
US5338822A (en) * 1992-10-02 1994-08-16 Cargill, Incorporated Melt-stable lactide polymer composition and process for manufacture thereof
US5525706A (en) * 1992-10-02 1996-06-11 Cargill, Incorporated Melt-stable lactide polymer nonwoven fabric and process for manufacture thereof
US6005068A (en) * 1992-10-02 1999-12-21 Cargill Incorporated Melt-stable amorphous lactide polymer film and process for manufacture thereof
US6005067A (en) * 1992-01-24 1999-12-21 Cargill Incorporated Continuous process for manufacture of lactide polymers with controlled optical purity
US6323307B1 (en) 1988-08-08 2001-11-27 Cargill Dow Polymers, Llc Degradation control of environmentally degradable disposable materials
US6326458B1 (en) 1992-01-24 2001-12-04 Cargill, Inc. Continuous process for the manufacture of lactide and lactide polymers
WO2018127270A1 (en) * 2017-01-04 2018-07-12 Pharmathen S.A. Process for preparing biodegradable polymers of high molecular weight
CN111647144A (en) * 2019-09-20 2020-09-11 上海浦景化工技术股份有限公司 Method for adjusting chain structure of polyglycolic acid molecule

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3839297A (en) * 1971-11-22 1974-10-01 Ethicon Inc Use of stannous octoate catalyst in the manufacture of l(-)lactide-glycolide copolymer sutures
NL8702563A (en) * 1987-10-28 1989-05-16 Cca Biochem B V POLYMER LACTIDE, METHOD FOR PREPARING SUCH A POLYMER LACTIDE, AND A COMPOSITION CONTAINING SUCH POLYMER LACTIDE.

Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6323307B1 (en) 1988-08-08 2001-11-27 Cargill Dow Polymers, Llc Degradation control of environmentally degradable disposable materials
US5225129A (en) * 1990-07-19 1993-07-06 Dsm N.V. Method for the manufacture of polymer products from cyclic esters
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
US5258488A (en) * 1992-01-24 1993-11-02 Cargill, Incorporated Continuous process for manufacture of lactide polymers with controlled optical purity
US5274073A (en) * 1992-01-24 1993-12-28 Cargill, Incorporated Continuous process for manufacture of a purified lactide
US6326458B1 (en) 1992-01-24 2001-12-04 Cargill, Inc. Continuous process for the manufacture of lactide and lactide polymers
US5357035A (en) * 1992-01-24 1994-10-18 Cargill, Incorporated Continuous process for manufacture of lactide polymers with purification by distillation
US5142023A (en) * 1992-01-24 1992-08-25 Cargill, Incorporated Continuous process for manufacture of lactide polymers with controlled optical purity
US6277951B1 (en) 1992-01-24 2001-08-21 Cargill, Incorporated Continuous process for manufacture of lactide polymers with controlled optical purity
US5484881A (en) * 1992-10-02 1996-01-16 Cargill, Inc. Melt-stable amorphous lactide polymer film and process for manufacturing thereof
US6143863A (en) * 1992-10-02 2000-11-07 Cargill, Incorporated Melt-stable lactide polymer composition and process for manufacture thereof
US5585191A (en) * 1992-10-02 1996-12-17 Cargill, Incorporated Melt-stable amorphous lactide polymer film and process for manufacture thereof
US5763564A (en) * 1992-10-02 1998-06-09 Cargill, Incorporated Melt-stable lactide polymer composition and process for manufacture thereof
US5773562A (en) * 1992-10-02 1998-06-30 Cargill, Incorporated Melt-stable semi-crystalline lactide polymer film and process for manufacture thereof
US5798436A (en) * 1992-10-02 1998-08-25 Cargill, Incorporated Melt-stable amorphous lactide polymer film and process for manufacture thereof
US5807973A (en) * 1992-10-02 1998-09-15 Cargill, Incorporated Melt-stable lactide polymer nonwoven fabric and process for manufacture thereof
US5981694A (en) * 1992-10-02 1999-11-09 Cargill, Incorporated Melt-stable lactide polymer composition and process for manufacture thereof
US6005068A (en) * 1992-10-02 1999-12-21 Cargill Incorporated Melt-stable amorphous lactide polymer film and process for manufacture thereof
US5536807A (en) * 1992-10-02 1996-07-16 Cargill, Incorporated Melt-stable semi-crystalline lactide polymer film and process for manufacture thereof
US6093791A (en) * 1992-10-02 2000-07-25 Cargill, Incorporated Melt-stable semi-crystalline lactide polymer film and process for manufacture thereof
US6111060A (en) * 1992-10-02 2000-08-29 Cargill, Incorporated Melt-stable lactide polymer nonwoven fabric and process for manufacture thereof
US6121410A (en) * 1992-10-02 2000-09-19 Cargill, Incorporated Melt-stable semi-crystalline lactide polymer film and process for manufacture thereof
US5539081A (en) * 1992-10-02 1996-07-23 Cargill, Incorporated Melt-stable lactide polymer composition and process for manufacture thereof
US6207792B1 (en) 1992-10-02 2001-03-27 Cargill, Incorporated Melt-stable amorphous lactide polymer film and process for manufacture thereof
US5525706A (en) * 1992-10-02 1996-06-11 Cargill, Incorporated Melt-stable lactide polymer nonwoven fabric and process for manufacture thereof
US5475080A (en) * 1992-10-02 1995-12-12 Cargill, Incorporated Paper having a melt-stable lactide polymer coating 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
US6355772B1 (en) 1992-10-02 2002-03-12 Cargill, Incorporated Melt-stable lactide polymer nonwoven fabric and process for manufacture thereof
WO2018127270A1 (en) * 2017-01-04 2018-07-12 Pharmathen S.A. Process for preparing biodegradable polymers of high molecular weight
CN110167990A (en) * 2017-01-04 2019-08-23 法尔玛赞公司 The method for being used to prepare high molecular weight biodegradable polymer
US11046810B2 (en) 2017-01-04 2021-06-29 Pharmathen S.A. Process for preparing biodegradable polymers of high molecular weight
AU2017391591B2 (en) * 2017-01-04 2022-12-22 Pharmathen S.A. Process for preparing biodegradable polymers of high molecular weight
CN111647144A (en) * 2019-09-20 2020-09-11 上海浦景化工技术股份有限公司 Method for adjusting chain structure of polyglycolic acid molecule
CN111647144B (en) * 2019-09-20 2022-08-02 上海浦景化工技术股份有限公司 Method for adjusting chain structure of polyglycolic acid molecule

Also Published As

Publication number Publication date
DE1595085A1 (en) 1970-01-22
DE1595085B2 (en) 1974-02-14
DE1595085C3 (en) 1974-09-26
IT998002B (en) 1976-01-20

Similar Documents

Publication Publication Date Title
GB1040168A (en) High molecular weight polylactides and a process for their preparation
GB1028928A (en) A process for the polymerization or copolymerization of cyclic esters of hydroxycarboxylic acids
US2543419A (en) Polycyclic di-epoxy ethers
US3268487A (en) Process for polymerization of lactides
US3021317A (en) Polymerization of cyclic esters
ATE137771T1 (en) POLYMERIZATION PROCESS AND POLYMERIZATION CATALYST
GB1089111A (en) High molecular weight polycarbonates
GB1526603A (en) Preparation of organic phosphites
GB859645A (en) Process for preparing lactone adducts and polyesters
US3021313A (en) Polymerization of cyclic esters
US3190858A (en) Polymerization of cyclic esters
US3039994A (en) Polyesters of hydroxybenzoic acids
US3025305A (en) Cyclic carbonate from olefin
US3021312A (en) Polymerization of cyclic esters
US3231586A (en) Diepoxide compositions
US2720503A (en) Organo-magnesium halide catalysts for the preparation of polyesters
US3021315A (en) Polymerization of cyclic esters
MX3328E (en) PROCEDURE FOR PREPARING 2-ARYL-PROPIONIC ACIDS
JPS4925243B1 (en)
US4220753A (en) Alkyl alkoxymethylbenzoates
US3516973A (en) Process for the polymerization of beta-lactones
US2916474A (en) Process of preparing polymeric terephthalic esters by interchange between a glycol and a dialkyl ester of terephthalic acid
GB1123019A (en) Silicon-substituted glycol monoesters
US3773822A (en) Process of making polyester polyols
GB1519534A (en) Moulding compositions including unsaturated polyesters and an amide of an unsaturated aliphatic carboxylic acid