Material Contains A Metal Atom Patents (Class 528/357)
  • Patent number: 5378801
    Abstract: The invention relates to a continuous process for the preparation of resorbable polyesters.
    Type: Grant
    Filed: August 3, 1993
    Date of Patent: January 3, 1995
    Inventors: Dieter Reichert, Franz D. Klingler, Horst Schwall, Albert Christmann, Berthold Buchholz
  • Patent number: 5359027
    Abstract: Polymers and copolymers of L(+) and D(-) lactic acid, with high molecular weight and in the absence of catalysts, are prepared by upgrading low molecular weight polymers in the solid state.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: October 25, 1994
    Assignee: Himont Incorporated
    Inventors: Gabriele Perego, Enrico Albizzati
  • Patent number: 5359026
    Abstract: A copolymerized poly(lactide) polymer. A lactide is copolymerized with an epoxidized fat, oil, or mixture thereof thereby resulting in poly(lactide) copolymers having improved processing properties over prior poly(lactide)s.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: October 25, 1994
    Assignee: Cargill, Incorporated
    Inventor: Patrick R. Gruber
  • Patent number: 5357035
    Abstract: A process for the continuous production of polylactide polymers from lactic acid which incorporates removal of water or a solvent carrier to concentrate the lactic acid feed followed by polymerization to a low-molecular-weight prepolymer. This prepolymer is fed to a reactor in which a catalyst is added to facilitate generation of lactide, the depolymerization product of polylactic acid. The lactide generated is continuously fed to a distillation system as a liquid or vapor wherein water and other impurities are removed. The resultant purified liquid lactide is fed directly to a polymerization process.
    Type: Grant
    Filed: September 16, 1993
    Date of Patent: October 18, 1994
    Assignee: Cargill, Incorporated
    Inventors: Patrick R. Gruber, Eric S. Hall, Jeffrey J. Kolstad, Matthew L. Iwen, Richard D. Benson, Ronald L. Borchardt
  • Patent number: 5357034
    Abstract: High molecular weight polylactic acid is generally produced by the polymerization of lactide. Lactide is prepared by the depolymerization of low molecular weight polylactic acid. There are difficulties in the preparation of high molecular weight polylactic acid and high purity lactide isomers due to the equilibrium between lactic acid, low molecular weight polylactic acid, high molecular weight polylactic acid, lactide and water. Further it has never been proposed to provide a continuous process to produce high molecular weight polylactic acid from lactic acid. The present invention overcomes the equilibrium problem and provides a continuous process.
    Type: Grant
    Filed: September 8, 1992
    Date of Patent: October 18, 1994
    Assignee: Camelot Technologies Inc.
    Inventors: Israel D. Fridman, John Kwok, Ronald J. Downey, Speros P. Nemphos
  • Patent number: 5349046
    Abstract: A method is disclosed for making a molded article of manufacture of polymerized .beta.-lactone which method involves injecting into a mold at least one .beta.-lactone monomer and at least one nucleophilic initiator, substantially polymerizing the .beta.-lactone in the mold and removing the resultant polymerized article from the mold.
    Type: Grant
    Filed: December 1, 1992
    Date of Patent: September 20, 1994
    Assignee: Shell Oil Company
    Inventors: Sharon M. Beshouri, Pui K. Wong, Dale L. Handlin, Jr.
  • Patent number: 5349047
    Abstract: Polyesters having predetermined monomeric sequence are produced by stepwise addition of monomeric hydroxyacids to a growing polymeric chain. Included herein are various polyesters having predetermined primary sequence, various methods of producing polyesters having predetermined primary sequence, various articles formed from polyesters having predetermined primary sequence and various methods of using such articles.
    Type: Grant
    Filed: June 16, 1993
    Date of Patent: September 20, 1994
    Assignee: United States Surgical Corporation
    Inventors: Matthew E. Hermes, Bin Huang
  • Patent number: 5346966
    Abstract: Linear stereo block copolymers are disclosed. The polymers comprise a plurality of alternating polymeric blocks of amorphous copolymers of L-lactide and D-lactide with semicrystalline blocks of either L-lactide homopolymer or D-lactide homopolymer. The molecular weight can be built up by either of two techniques. The first technique is to use a chain extending agent such as a diacyl chloride or a diisocyanate to link a plurality of the preformed block copolymers. The second technique is to polymerize additional alternating amorphous and semicrystalline segments or blocks onto the original alternating block copolymers.
    Type: Grant
    Filed: October 26, 1993
    Date of Patent: September 13, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Maria Spinu
  • Patent number: 5338822
    Abstract: A lactide polymer composition combining compositional and purity limitations and catalyst optimization or addition of stabilizing agents resulting in a melt-stable polymer is disclosed. The melt-stable lactide polymer comprises a plurality of polylactide polymer chains, residual lactide in concentration of less than 2 percent and water in concentration of less than 1000 parts-per-million. A stabilizing agent in an amount sufficient to reduce depolymerization of the lactide polymer during melt-processing or alternatively, control of catalyst level at a molar ratio of monomer to catalyst greater than 3000:1 is also included in the melt-stable composition. A process for manufacture of a melt-stable lactide polymer composition includes polymerizing a lactide mixture and adding stabilizing agents sufficient to reduce depolymerization of the polylactide during melt-processing, followed by devolatilizing the polylactide to remove monomer and water.
    Type: Grant
    Filed: October 2, 1992
    Date of Patent: August 16, 1994
    Assignee: Cargill, Incorporated
    Inventors: Patrick R. Gruber, Jeffrey J. Kolstad, Eric S. Hall, Robin S. Eichen Conn, Christopher M. Ryan
  • Patent number: 5324307
    Abstract: A one piece surgical repair device consists essentially of a polymeric wire. The polymeric wire is comprised of an oriented, semicrystalline polymer. The surgical repair device can be a staple and is capable of permanent flexural deformation at ambient temperature.
    Type: Grant
    Filed: November 27, 1991
    Date of Patent: June 28, 1994
    Assignee: American Cyanamid Company
    Inventors: Peter K. Jarrett, Donald J. Casey, Louis Rosati, James W. Dwyer
  • Patent number: 5322925
    Abstract: Block copolymers have a first copolymer block wherein lactide is the predominant component and a second copolymer block wherein trimethylene carbonate is the predominant component. The copolymers are useful in forming surgical devices, including monofilament sutures.
    Type: Grant
    Filed: March 19, 1993
    Date of Patent: June 21, 1994
    Assignee: United States Surgical Corporation
    Inventors: Ross R. Muth, Nagabhushanam Totakura, Cheng-Kung Liu
  • Patent number: 5310865
    Abstract: A process for preparing polyhydroxycarboxylic acid by conducting a dehydration condensation of a hydroxycarboxylic acid or an oligomer thereof in a reaction mixture containing an organic solvent substantially in the absence of water and the polyhydroxycarboxylic acid thus obtained. The process provides polyhydroxycarboxylic acid having excellent properties and processability.
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: May 10, 1994
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Katashi Enomoto, Masanobu Ajioka, Akihiro Yamaguchi
  • Patent number: 5310599
    Abstract: A method providing a catalyzed ring opening polyester polymerization at a high reaction rate wherein the amount of organic acid in the reaction medium is maintained at an acid: catalyst ratio below 6:1.
    Type: Grant
    Filed: May 6, 1993
    Date of Patent: May 10, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Thomas M. Ford
  • Patent number: 5296567
    Abstract: The present document describes the use of an inhibitor for cationic polymerization as an additive to a thermocurable composition based on at least one cationically polymerizable organic material and an initiator for cationic polymerization in the form of an onium compound or a compound of the formula (I)[M.sup.+n (L).sub.x ].sup.n+ nX.sup.- (I),in which n is 2 or 3, M is a metal cation selected from the group comprising Zn.sup.2+, Mg.sup.2+, Fe.sup.2+, Co.sup.2+, Ni.sup.2+, Cr.sup.2+, Ru.sup.2+, Mn.sup.2+, Sn.sup.2+, VO.sup.2+, Fe.sup.3+, Al.sup.3+ and Co.sup.3+, X.sup.- is an anion selected from the group comprising PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, BiF.sub.6.sup.-, derivatives of these anions in which at least one fluorine atom has been replaced by a hydroxyl group, and CF.sub.3 SO.sub.3.sup.-, or in which up to 50% of the anions X.sup.-, based on the total amount of anions, may be any desired anions, L is water or an organic .sigma.
    Type: Grant
    Filed: April 6, 1992
    Date of Patent: March 22, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Baumann, Werner Margotte, Beat Muller
  • Patent number: 5292859
    Abstract: A process for polymerizing lactide and up to 20 mole percent of another lactone is disclosed. The cayalysts used have the formula MZ.sub.3 wherein M is scandium, yttrium, bismuth, a lanthanide series rare earth metal or a mixture thereof and the Zs are independently the same or different highly coordinating ligands. The preferred metals M are lanthanum, cerium, praseodymium and neodymium with lanthanum being especially preferred. The preferred ligands are betadiketones, betaketoesters and malonate anions with the betadiketones such as 2,2,6,6-tetramethyl-3,5-heptanedionates being especially preferred.
    Type: Grant
    Filed: December 22, 1992
    Date of Patent: March 8, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Thomas M. Ford, Stephan J. McLain
  • Patent number: 5288841
    Abstract: An improved process for the ring-opening polymerization of ring-opening polymerizable cyclic compounds using a fluidized bed.
    Type: Grant
    Filed: November 30, 1992
    Date of Patent: February 22, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Howard E. Bellis, Donald C. Paul
  • Patent number: 5274073
    Abstract: A process for the continuous conversion of crude lactic acid to a substantially purified lactide or polylactide including the steps of polymerizing the lactic acid to form a prepolymer with subsequent depolymerization to form a crude lactide in the presence of a catalyst. The crude lactide is purified in an improved distillation system in which at least three fractions are formed with the substantially purified lactide removed as an intermediate boiling sidedraw stream. The substantially purified lactide may then be polymerized.
    Type: Grant
    Filed: August 24, 1992
    Date of Patent: December 28, 1993
    Assignee: Cargill, Incorporated
    Inventors: Patrick R. Gruber, Eric S. Hall, Jeffrey J. Kolstad, Matthew L. Iwen, Richard D. Benson, Ronald L. Borchardt
  • Patent number: 5270400
    Abstract: Linear block copolymers are disclosed. The polymers comprise a plurality of alternating polymeric blocks of amorphous copolymers of L-lactide and D-lactide with semicrystalline blocks of either L-lactide homopolymer or D-lactide homopolymer. The molecular weight can be built up by either of two techniques. The first technique is to use a chain extending agent such as a diacyl chloride or a diisocyanate to link a plurality of the preformed block copolymers. The second technique is to polymerize additional alternating amorphous and semicrystalline onto the original alternating block copolymers.
    Type: Grant
    Filed: December 31, 1991
    Date of Patent: December 14, 1993
    Inventor: Maria Spinu
  • Patent number: 5264547
    Abstract: An optically active 7-substituted-1,4-dioxepan-5-one derivative represented by the general formula (I): ##STR1## wherein R represents an alkyl group having from 1 to 5 carbon atoms; and * means an asymmetric carbon atom, is disclosed. An optically active polymer represented by formula (II): ##STR2## wherein R and * are as defined above; and n is an integer of 25 or more, obtained by ring opening polymerization of the optically active 7-substituted-1,4-dioxepan-5-one derivative represented by formula (I) is also disclosed. A process for producing the optically active polymer represented by formula (II) is further disclosed, comprising subjecting an optically active 7-substituted-1,4-dioxepan-5-one derivative represented by formula (I) to ring opening polymerization in the presence of at least one catalyst selected from the group consisting of (i) an organotin compound, (ii) an organoaluminum compound and water, and (iii) an organozinc compound and water.
    Type: Grant
    Filed: March 2, 1993
    Date of Patent: November 23, 1993
    Assignee: Takasago International Corporation
    Inventors: Akio Yamaguchi, Yoji Hori, Susumu Akutagawa
  • Patent number: 5258488
    Abstract: A process for the continuous production of polylactide polymers from lactic acid which incorporates removal of water or a solvent carrier to concentrate the lactic acid feed followed by polymerization to a low-molecular-weight prepolymer. This prepolymer is fed to a reactor in which a catalyst is added to facilitate generation of lactide, the depolymerization product of polylactic acid. The lactide generated is continuously fed to a distillation system as a liquid or vapor wherein water and other impurities are removed. The resultant purified liquid lactide is fed directly to a polymerization process.
    Type: Grant
    Filed: August 7, 1992
    Date of Patent: November 2, 1993
    Assignee: Cargill, Incorporated
    Inventors: Patrick R. Gruber, Eric S. Hall, Jeffrey J. Kolstad, Matthew L. Iwen, Richard D. Benson, Ronald L. Borchardt
  • Patent number: 5256762
    Abstract: Compositions comprising polyesters having predetermined monomeric sequence are produced by stepwise addition of monomeric hydroxyacids to a growing polymeric chain. Included herein are various polyesters having predetermined monomeric sequence, methods of their production use as well as articles formed from said compositions.
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: October 26, 1993
    Assignee: United States Surgical Corporation
    Inventors: Matthew E. Hermes, Ross R. Muth
  • Patent number: 5248761
    Abstract: Compositions comprising amino acid terminated polyesters having predetermined monomeric sequence are produced by stepwise addition of monomeric hydroxyacids to an amine to form a growing polymeric chain. Included herein are various amino acid terminated polyesters having predetermined monomeric sequence, methods for their production and use as well as articles formed from said compositions.
    Type: Grant
    Filed: August 12, 1992
    Date of Patent: September 28, 1993
    Assignee: United States Surgical Corporation
    Inventor: Matthew E. Hermes
  • Patent number: 5247058
    Abstract: A process for the continuous production of polylactide polymers from lactic acid which incorporates removal of water or a solvent carrier to concentrate the lactic acid feed followed by polymerization to a low-molecular-weight prepolymer. This prepolymer is fed to a reactor in which a catalyst is added to facilitate generation of lactide, the depolymerization product of polylactic acid. The lactide generated is continuously fed to a distillation system as a liquid or vapor wherein water and other impurities are removed. The resultant purified liquid lactide is fed directly to a polymerization process.
    Type: Grant
    Filed: August 7, 1992
    Date of Patent: September 21, 1993
    Assignee: Cargill, Incorporated
    Inventors: Patrick R. Gruber, Eric S. Hall, Jeffrey J. Kolstad, Matthew L. Iwan, Richard D. Benson, Ronald L. Borchardt
  • Patent number: 5247059
    Abstract: A process for the continuous production of substantially purified lactide and lactide polymers from an ester of lactic acid including the steps of forming crude lactide in the presence of a catalyst means to form a condensation reaction by-product and polylactic acid and depolymerizing the polylactic acid molecules followed by subsequent purification of the crude lactide in a distillation system. A purified lactide is then polymerized.
    Type: Grant
    Filed: August 24, 1992
    Date of Patent: September 21, 1993
    Assignee: Cargill, Incorporated
    Inventors: Patrick R. Gruber, Eric S. Hall, Jeffrey J. Kolstad, Matthew L. Iwen, Richard D. Benson, Ronald L. Borchardt
  • Patent number: 5235031
    Abstract: A process for polymerizing lactide and up to 20 mole percent of another lactone in the absence of solvent at 100.degree. to 220.degree. C. using an yttrium or lanthanide series rare earth metal catalyst.
    Type: Grant
    Filed: March 13, 1992
    Date of Patent: August 10, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Neville E. Drysdale, Thomas M. Ford, Stephan J. McLain
  • Patent number: 5225129
    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.
    Type: Grant
    Filed: July 18, 1991
    Date of Patent: July 6, 1993
    Assignee: DSM N.V.
    Inventor: Hendrik J. van den Berg
  • Patent number: 5218087
    Abstract: Disclosed is a method for modifying a medical material of lactic acid polymer, the method comprising heat-treating the material at a temperature which is not lower than 100.degree. C. and is lower than the melting point of the polymer for at least 10 minutes while continuously releasing the gas from the system.
    Type: Grant
    Filed: February 15, 1991
    Date of Patent: June 8, 1993
    Assignee: Gunze Limited
    Inventors: Masakazu Suzuki, Yoshikiyo Saito, Yoshikiyo Ikada, Hye H. Shuon
  • Patent number: 5208297
    Abstract: A process for polymerizing lactide and up to 20 mole percent of another lactone is disclosed. The cayalysts used have the formula MZ.sub.3 wherein M is scandium, yttrium, bismuth, a lanthanide series rare earth metal or a mixture thereof and the Zs are independantly the same or different highly coordinating ligands. The preferred metals M are lanthanum, cerium, praseodymium and neodymium with lanthanum being especially preferred. The preferred ligands are betadiketones, betaketoesters and malonate anions with the beta diketones such as 2,2,6,6-tetramethyl-3,5-heptanedionates being especially preferred.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: May 4, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Thomas M. Ford, Stephan J. McLain
  • Patent number: 5179179
    Abstract: Initiator compositions for materials which can be polymerized cationically are described, these containingi) an anhydride of a polycarboxylic acid, a polyisocyanate, a cyclic carbonate, a lactone or a mixture of such compounds, and dissolved thereinii) at least one compound of the formula I[M.sup.+n (L).sub.x ].sup.n+ nX.sup.- (I)in which n is 2 or 3, M is a metal cation selected from the group consisting of Zn.sup.2+, Mg.sup.2+, Fe.sup.2+, Co.sup.2+, Ni.sup.2+, Cr.sup.2+, Ru.sup.2+, Mn.sup.2+, Sn.sup.2+, VO.sup.2+, Fe.sup.3+, Al.sup.3+ and Co.sup.3+, X.sup.- is an anion which is selected from the group consisting of AsF.sub.6.sup.-, SbF.sub.6.sup.-, BiF.sub.6.sup.- and derivatives derived from these anions in which a fluorine atom is replaced by hydroxyl groups, or in which up to 50% of the anions X.sup.-, based on the total amount of anions, can also be any desired anions, L is water or an organic .sigma.
    Type: Grant
    Filed: April 27, 1992
    Date of Patent: January 12, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Beat Muller, Dieter Baumann
  • Patent number: 5142023
    Abstract: A process for the continuous production of polylactide polymers from lactic acid which incorporates removal of water or a solvent carrier to concentrate the lactic acid feed followed by polymerization to a low-molecular-weight prepolymer. This prepolymer is fed to a reactor in which a catalyst is added to facilitate generation of lactide, the depolymerization product of polylactic acid. The lactide generated is continuously fed to a distillation system as a liquid or vapor wherein water and other impurities are removed. The resultant purified liquid lactide is fed directly to a polymerization process.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: August 25, 1992
    Assignee: Cargill, Incorporated
    Inventors: Patrick R. Gruber, Eric S. Hall, Jeffrey J. Kolstad, Matthew L. Iwen, Richard D. Benson, Ronald L. Borchardt
  • Patent number: 5136018
    Abstract: Macrocyclic polyarylate oligomers containing a mixture of isophthalate and terephthalate moieties are prepared by reaction of a mixture of isophthaloyl and terephthaloyl chloride with one or more bisphenols under specific reaction conditions. They are characterized by a reduced degree of crystallinity and therefore lower processing temperatures than the corresponding isophthalate oligomers.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: August 4, 1992
    Assignee: General Electric Company
    Inventors: Eugene P. Boden, Peter D. Phelps
  • Patent number: 5133739
    Abstract: Crystalline copolymer comprising the reaction product of: a) a predominant amount of a high molecular weight prepolymer of .epsilon.-caprolactone and glycolide, and b) the balance glycolide. A surgical device such as a surgical filament, in particular a surgical suture, prepared by injection molding or melt spinning the crystalline copolymer.
    Type: Grant
    Filed: May 13, 1991
    Date of Patent: July 28, 1992
    Assignee: Ethicon, Inc.
    Inventors: Rao S. Bezwada, Dennis D. Jamiolkowski, Shalaby W. Shalaby
  • Patent number: 5132397
    Abstract: Copolymers of lactic acid, from 0.5 to 20 weight % of 4-valerolactone and from 0 to 20 weight % of a C.sub.6-8 lactone form polymers having a higher intrinsic viscosity than homopolymers of lactic acid per se. The polymers also have an increased heat stability over the homopolymer of lactic acid.
    Type: Grant
    Filed: April 2, 1991
    Date of Patent: July 21, 1992
    Assignee: Polysar Financial Services S.A.
    Inventor: Andrea A. DeGuia
  • Patent number: 5130406
    Abstract: Initiator compositions for materials which can be polymerized cationically are described, these containingi) an anhydride of a polycarboxylic acid, a polyisocyanate, a cyclic carbonate, a lactone or a mixture of such compounds, and dissolved thereinii) at least one compoumd of the formula I[M.sup.+n (L).sub.x ].sup.n+ nX.sup.- (I)in which n is 2 or 3, M is a metal cation selected from the group consisting of Zn.sup.2+, Mg.sup.2+, Fe.sup.2+, Co.sup.2+, Ni.sup.2+, Cr.sup.2+, Ru.sup.2+, Mn.sup.2+, Sn.sup.2+, VO.sup.2+, Fe.sup.3+, Al.sup.3+ and Co.sup.3+, X.sup.- is an anion which is selected from the group consisting of AsF.sub.6.sup.-, SbF.sub.6.sup.-, BiF.sub.6.sup.- and derivatives derived from these anions in which a fluorine atom is replaced by hydroxyl groups, or in which up to 50% of the anions X.sup.-, based on the total amount of anions, can also be any desired anions, L is water or an organic .sigma.
    Type: Grant
    Filed: March 19, 1990
    Date of Patent: July 14, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Beat Muller, Dieter Baumann
  • Patent number: 5116932
    Abstract: Polyurethane resins having excellent hydrolysis resistance are prepared from copolymerized caprolactone polyol obtained by the copolymerization of .epsilon.-caprolactone with trimethylcaprolactone having side chains as a diol component. The polyurethane resins so-obtained have excellent hydrolysis resistance, and retain high levels of mechanical strength, more excellent resistance under high heat and moisture conditions, etc., thereby maintaining a good balance of properties and are useful in a very wide variety of forms including spandex, rigid or flexible urethane foams, thermoplastic urethane elastomers, thermosetting urethane elastomers, adhesives, synthetic leather, and paints, etc.
    Type: Grant
    Filed: July 18, 1990
    Date of Patent: May 26, 1992
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Takaaki Fujiwa
  • Patent number: 5082922
    Abstract: A method is provided for producing a modified addition polymer from an ethylenically unsaturated monomer composition that includes at least one monomer having hydroxyl or carboxyl functionality. The ethylenically unsaturated monomer composition, and a free radical initiator therefor, is dissolved in a solvent-free molten composition maintained at an addition polymerization temperature, the molten composition comprising a cyclic compound reactive via ring-opening with the hydroxyl or carboxyl functionality. The resulting material is useful in the manufacture of paints in liquid or powder form.
    Type: Grant
    Filed: October 12, 1988
    Date of Patent: January 21, 1992
    Assignee: The Valspar Corporation
    Inventors: Larry B. Brandenburger, Philip J. Ruhoff
  • Patent number: 5053485
    Abstract: A polymer lactide is prepared by the polymerization of meso-3,6-dimethyl-1,4-dioxane-2,5-dione or mesodilactide and, if desired, other monomers. The mesolactide monomer has preferably a free acid content of less than 1 meq/kg dilactide and is then polymerized in a manner known per se. The compositions containing polymesolactide obtained according to this process do not posess the typical characteristics of poly-DL-lactide, poly-D-lactide or poly-L-lactide. A shorter degradation time of a substrate based on the present polymer is unofficial for several purposes. The present polymers have a good biocompatibility and are thus suited for bone plates, clamps and sutures and controlled release of biologically active compounds. The present polylactides and/or copolymers thereof have the benefit of a good biodegradability, biocompatibility, non-toxicity and non-mutagenicity.
    Type: Grant
    Filed: June 12, 1990
    Date of Patent: October 1, 1991
    Assignee: C.C.A. Biochem B.V.
    Inventors: Jan Nieuwenhuis, Arie C. Mol
  • Patent number: 5032671
    Abstract: Lactone monomers are polymerized using double metal cyanide compounds as catalysts to yield useful lactone polymers. Block or random copolymers of lactones and epoxides may also be prepared.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: July 16, 1991
    Assignee: Arco Chemical Technology, Inc.
    Inventor: Stephen D. Harper
  • Patent number: 5028667
    Abstract: Process for yttrium and rare earth compound catalyzed polymerization of lactones and the living polymer compositions of such polymerizations, novel polyester products of such polymerizations and novel yttrium and rare earth metal compounds useful as catalysts in the polymerization of biodegradable polymers for medical uses and flexible films for packaging.
    Type: Grant
    Filed: September 29, 1989
    Date of Patent: July 2, 1991
    Assignee: E.I. Du Pont de Nemours and Company
    Inventors: Stephan J. McLain, Neville E. Drysdale
  • Patent number: 5023316
    Abstract: A method of polymerizing at least one .beta.-substituted-.beta.-propiolactone in the presence of a catalytic amount of isobutylaluminoxane in a solvent for the .beta.-propiolactone(s) and isobutylaluminoxane for a time and at a temperature to produce a poly(.beta.-substituted-.beta.-propiolactone) polyester and the polyesters produced thereby are disclosed.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: June 11, 1991
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Manuela Benvenuti, Robert W. Lenz
  • Patent number: 5006637
    Abstract: Copolyestercarbonates are prepared by the reaction of at least one cyclic polycarbonate oligomer with at least one cyclic polyester oligomer in the presence of a cyclic polycarbonate polymerization catalyst at temperatures in the range of about 280.degree.-375.degree. C. Mixtures of bisphenol A polycarbonate and bisphenol A isophthalate or terephthalate oligomers are preferably employed, and the preferred catalysts are tetraarylborate salts such as tetra-n-butylammonium tetraphenylborate.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: April 9, 1991
    Assignee: General Electric Company
    Inventors: Thomas L. Guggenheim, James M. Fukuyama, John J. Kelly
  • Patent number: 5003038
    Abstract: In a first stage, a lactone is polymerized by an ionic route in vinyl chloride with the aid of a catalyst consisting of the product, optionally complexed with tetrahydrofuran, of the reaction of an alkylmetal with ethylenically unsaturated alcohol, optionally in the presence of water and, in a second stage, the said vinyl chloride is polymerized by a radical route in an aqueous suspension and in the presence of the polymerization medium originating from the first stage, to which other unsaturated monomers are optionally added.The invention also relates to new modified vinyl chloride polymers consisting of lactone polymers whose number-average molecular weight is less than 5,000, grafted with vinyl chloride polymers.
    Type: Grant
    Filed: March 12, 1990
    Date of Patent: March 26, 1991
    Assignee: Solvay & Cie (Societe Anonyme)
    Inventors: Pierre Malfroid, Qui L. Nguyen, Nicole Dewaele, Jean-Marie Blondin, Jean-Paul Burnay
  • Patent number: 4994551
    Abstract: Novel, semi-crystalline depsipeptide polymers and copolymers particularly suitable for use in fabricating bioabsorbable medical implant devices such as sutures or clips and obtained through ring-opening polymerization of certain 3-substituted-2,5-morpholinediones prepared by reacting a naturally occurring alpha-amino acid with an alpha-halo acid chloride in inert solvent in the presence of an acid acceptor.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: February 19, 1991
    Assignee: Pfizer Inc.
    Inventors: Fu-Ning Fung, Raymond C. Glowaky
  • Patent number: 4983689
    Abstract: Preparation of a macromolecular monomer of a lactone having an alpha-beta monoolefinically unsaturated "head" is effected at low temperature with a strong oxonium salt, such as a trialkyloxonium (TAO) hexafluorophosphate catalyst, with essentially no formation of cyclic oligomers and an insignificant amount of diacrylate. Cationic ring-opening polymerization of lactone monomer in conjunction with an unsaturated alcohol (propagator) having an acryloyl or methacryloyl double bond, produces a polylactone macromer having an ethylenic double bond at one end and a hydroxyl group at the other. The polymerization proceeds by polyaddition of the lactone to the OH group which is the propagating species. The macromer so formed allows the preparation of a macromer of block copolymer of the polylactone with a polyether such as epichlorohydrin, using the same TAO catalyst. In such a macromer of block copolymer, the polylactone ester block is next to the double bond, followed by the polyether block.
    Type: Grant
    Filed: December 12, 1988
    Date of Patent: January 8, 1991
    Inventor: Simon H. Yu
  • Patent number: 4859763
    Abstract: A process for copolymerizing lactide and glycolide by using a specific amount of stannous octoate as a catalyst in the presence of a polymerization regulator at temperature of 200.degree.-230.degree. C. to prepare dl-lactic acid-glycolic acid-copolymers which contain 50-60 mol % of a dl-lactic acid unit and 40-50 mol % of a glycolic acid unit and have inherent viscosity of 0.4-0.6 in chloroform.
    Type: Grant
    Filed: July 8, 1988
    Date of Patent: August 22, 1989
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Hiroshi Takayanagi, Tadashi Kobayashi, Takayoshi Masuda, Hosei Shinoda
  • Patent number: 4838267
    Abstract: Block copolymers of glycolide and p-dioxanone are produced by reacting poly(p-dioxanone) that is substantially free of p-dioxanone monomer with glycolide.
    Type: Grant
    Filed: February 12, 1988
    Date of Patent: June 13, 1989
    Assignee: Ethicon, Inc.
    Inventors: Dennis D. Jamiolkowski, Shalaby W. Shalaby, Rao S. Bezwada, Hugh D. Newman, Jr.
  • Patent number: 4757132
    Abstract: Cyclic polyester and especially polyarylate oligomers, typically having degrees of polymerization from 2 to about 7, are prepared by reacting a bisphenol such as bisphenol A or 6,6'-dihydroxy-3,3,3',3'-tetramethylspiro(bis)indane with a dicarboxylic acid chloride such as isophthaloyl or terephthaloyl chloride in the presence of a catalyst, under conditions of low concentration. The cyclic oligomers may be polymerized to linear polyesters by contact with a transesterification catalyst at a temperature in the range of about 200.degree.-300.degree. C.
    Type: Grant
    Filed: October 20, 1986
    Date of Patent: July 12, 1988
    Assignee: General Electric Company
    Inventors: Daniel J. Brunelle, Thomas G. Shannon
  • Patent number: 4699974
    Abstract: Cyclic polycarbonate oligomer compositions are polymerized with lactones in the presence of a catalyst for the polymerization of either. Usually, the lactone is first polymerized at a lower temperature, followed by the cyclic polycarbonate at a higher temperature.
    Type: Grant
    Filed: August 7, 1986
    Date of Patent: October 13, 1987
    Assignee: General Electric Company
    Inventor: Thomas L. Evans
  • Patent number: 4683287
    Abstract: Described herein are compositions containing a reactive monomer derived from the reaction product of a hydroxyalkyl acrylate or methacrylate and a lactone. These compositions can be reacted with other ethlenically unsaturated monomers to produce curable oligomers and polymers than can be made into high quality industrial finishes by incorporation of various conventional crosslinking agents, plus other normally used formulating ingredients.
    Type: Grant
    Filed: August 14, 1986
    Date of Patent: July 28, 1987
    Assignee: Union Carbide Corporation
    Inventors: Joseph V. Koleske, Linda A. Domeier
  • Patent number: 4665134
    Abstract: A block copolymer having a narrow molecular weight distribution is produced by reacting an acid anhydride with an epoxide to yield a polyester, which is further reacted with a lactone, using a catalyst system comprising an aluminum porphyrin complex and an organic quaternary salt under mild reaction conditions.
    Type: Grant
    Filed: July 2, 1985
    Date of Patent: May 12, 1987
    Assignee: Hitachi Chemical Company Ltd.
    Inventors: Shohei Inoue, Takuzo Aida