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Method for the manufacture of polymer products from cyclic esters

Assignee: University of Groningen
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Filing: 1991-07-18
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Granted: 1993-07-06
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Expires: 2011-07-18
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Abstract

Abstract A method for the manufacture of polymer products from cyclic esters, according to which a catalyst and cyclic monomers are mixed in a mixing chamber and are optionally brought to a higher temperature, after which the mixture is injected, under pressure, into a cavity of a mold consisting of at least two parts and the mold is heated for some time at a temperature above the melting temperature of the monomers, after which the mold is opened and the product is removed from the mold. Polymer products manufactured by this method can be used in medical fields and particularly in reconstructive orthopedics.

Inventors

  • 👤 Hendrik J. van den Berg

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 13:46
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/02; C08G63/06; C08G63/08

Claims Analysis

Total Claims: 26
Claim 1
Independent Claim 219 words
Method of manufacturing a polymer product from cyclic monomers comprising the steps of: combining the cyclic monomers and a catalyst in a mixing chamber to form a mixture, injecting the mixture, under pressure, into a cavity of a mold having at least two parts, which mold is heated to a temperature above the melting temperature of the monomers, whereby the monomers polymerize allowing the polymerization to take place in the mold for 30 to 200 hours to obtain a degree of polymerization greater than 95% and an intrinsic viscosity of the polymer product greater than 8, opening the mold to remove the product from the mold, wherein the cyclic monomers are selected from the lactone group consisting of lactide, glycolide, ε-caprolactone, dioxanone, 1,4-dioxane-2,3-dione, beta-propiolactone, tetramethylglycolide, beta-butyrolactone, gamma-butyrolactone, pivalolactone, and the cyclic carbonate group consisting of trimethylene carbonate, 2,2-dimethyltrimethylene carbonate, and mixtures thereof, and wherein the catalyst is tin cotoate, antimony trifluoride, zinc powder, dibutyl tin oxide, tin oxalate or a compound according to Formula I: ##STR2## M being a metal ion and n being a number between 1 and 4, equal to the valence of the metal ion, and R 1 and R 2 being, independently of one another, an alkyl, aryl or cycloaliphatic group, and R 3 being an alkyl, aryl or cycloaliphatic group, or a hydrogen atom.
Claim 2
Dependent Claim 219 words
Method of manufacturing a polymer product from cyclic monomers comprising the steps of: combining the cyclic monomers and a catalyst in a mixing chamber to form a mixture, injecting the mixture, under pressure, into a cavity of a mold having at least two parts, which mold is heated to a temperature above the melting temperature of the monomers, whereby the monomers polymerize allowing the polymerization to take place in the mold for 30 to 200 hours to obtain a degree of polymerization greater than 95% and an intrinsic viscosity of the polymer product greater than 8, opening the mold to remove the product from the mold, wherein the cyclic monomers are selected from the lactone group consisting of lactide, glycolide, ε-caprolactone, dioxanone, 1,4-dioxane-2,3-dione, beta-propiolactone, tetramethylglycolide, beta-butyrolactone, gamma-butyrolactone, pivalolactone, and the cyclic carbonate group consisting of trimethylene carbonate, 2,2-dimethyltrimethylene carbonate, and mixtures thereof, and wherein the catalyst is tin cotoate, antimony trifluoride, zinc powder, dibutyl tin oxide, tin oxalate or a compound according to Formula I: ##STR2## M being a metal ion and n being a number between 1 and 4, equal to the valence of the metal ion, and R 1 and R 2 being, independently of one another, an alkyl, aryl or cycloaliphatic group, and R 3 being an alkyl, aryl or cycloaliphatic group, or a hydrogen atom.
Claim 3
Dependent Claim 25 words
Method according to claim 1, wherein each of lactide, glycolide, ε-caprolactone, dioxanone, 1,4-dioxane-2,3-dione, beta-propiolactone, tetramethylglycolide, beta-butyrolactone, gamma-butyrolactone, and pivalolactone consists essentially of optically pure isomers.
Claim 4
Dependent Claim 31 words
Method according to claim 1, wherein each of lactide, glycolide, ε-caprolactone, dioxanone, 1,4-dioxane-2,3-dione, beta-propiolactone, tetramethylglycolide, beta-butyrolactone, gamma-butyrolactone, and pivalolactone consists essentially of a mixture of two or more optically different isomers.
Claim 5
Dependent Claim 16 words
Method according to claim 1, wherein the alkyl, aryl or cycloaliphatic groups are substituted by halogen.
Claim 6
Dependent Claim 38 words
Method according to claim 1, wherein the catalyst is a compound according to Formula I, M is Zn 2 +, R 1 is a tertiary butyl group, R 2 is an ethyl group and R 3 is hydrogen.
Claim 7
Dependent Claim 33 words
Method according to claim 1, wherein the catalyst is a compound according to Formula I, M is Sn 2 +, R 1 and R 2 are methyl groups and R 3 is hydrogen.
Claim 8
Dependent Claim 16 words
Method according to claim 1, wherein the monomer/catalyst molecular ratio is from 1,000 to 300,000 (mol/mol).
Claim 9
Dependent Claim 16 words
Method according to claim 7, wherein the monomer/catalyst molecular ratio is from 5,000 to 30,000 (mol/mol).
Claim 10
Dependent Claim 16 words
Method according to claim 1, wherein the mold comprises walls made at least partially of steel.
Claim 11
Dependent Claim 25 words
Method according to claim 1, wherein the cyclic monomers are allowed to react at a temperature wherein said cyclic monomers are in a liquid state.
Claim 12
Dependent Claim 17 words
Method according to claim 10, wherein the temperature is in a range from 80° to 180° C.
Claim 13
Dependent Claim 14 words
Method according to claim 11, wherein the range is from 105° to 130° C.
Claim 14
Dependent Claim 39 words
Method according to claim 1, wherein the polymerization is allowed to take place for from 70 to 200 hours to obtain a degree of conversion greater than 98% and an intrinsic viscosity of the polymer product greater than 11.
Claim 15
Dependent Claim 26 words
Method according to claim 1, wherein the cavity of the mold defines a shape substantially the same as a shape of the product to be manufactured.
Claim 16
Dependent Claim 25 words
Method according to claim 1, wherein, in the injecting step, the mixture is injected into a bag of flexible material previously placed in the mold.
Claim 17
Dependent Claim 27 words
Method according to claim 15, wherein the bag is smaller than the cavity in the mold, thereby causing the bag to stretch when the mixture is injected.
Claim 18
Dependent Claim 33 words
Method according to claim 15, wherein the bag is introduced into the mold by inflating an amount of material into the mold to form a bag on an inside surface of the mold.
Claim 19
Dependent Claim 16 words
Process according to claim 15, wherein the product is removed from the mold in the bag.
Claim 20
Dependent Claim 20 words
Method according to claim 1, wherein an amount of fibrous reinforcement is combined with the mixture during the combining step.
Claim 21
Dependent Claim 11 words
Method according to claim 19, wherein the fibrous reinforcement is biocompatible.
Claim 22
Dependent Claim 11 words
Method according to claim 19, wherein the fibrous reinforcement is biodegradable.
Claim 23
Dependent Claim 20 words
Method according to claim 1, wherein an amount of fibrous reinforcement is brought into the mold before the injecting step.
Claim 24
Dependent Claim 11 words
Method according to claim 22, wherein the fibrous reinforcement is biocompatible.
Claim 25
Dependent Claim 11 words
Method according to claim 22, wherein the fibrous reinforcement is biodegradable.
Claim 26
Dependent Claim 17 words
Process according to claim 1, wherein the polymerization is allowed to take place under N 2 .

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1996-07-05 1997-01-04 1997-07-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2000-07-05 2001-01-04 2001-07-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2004-07-05 2005-01-04 2005-07-06 $7700.00 Window Closed / Lapsed

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