Material Contains A Metal Atom Patents (Class 528/357)
  • Patent number: 6433130
    Abstract: The present inventors has its objects to provide a polymerization catalyst component, a copper compound which can easily be synthesized and is stable. The present invention is related to a method of producing a polymer which comprises using a copper compound represented by the general formula CuXn, LCuXn or L(L′)CnXn (wherein L and L′ each represents a ligand, X represents a halogen atom or an alkoxy, thioxy, allyloxy, amino, secondary amino, tertiary amino, cyano, nitro, alkyl or allyl group, and n represents an integer of 0 to 2) as a catalyst and/or polymerization initiator in polymerizing a vinyl monomer whose polarity value e, when expressed in terms of absolute value, is not more than 1.5.
    Type: Grant
    Filed: February 12, 2001
    Date of Patent: August 13, 2002
    Assignee: Sekisui Chemical Co., Ltd.
    Inventors: Koichi Shibayama, Masao Ogasa
  • Patent number: 6426396
    Abstract: Poly(cyclic conjugated diene) polymers are prepared by polymerizing a cyclic conjugated diene monomer or cyclic conjugated diene monomer and a double bond-containing monomer using a transition metal catalyst, preferably a Ni-based catalyst, in a non-polar solvent containing a basic compound or an aromatic halide solvent. The poly(cyclic conjugated diene) polymer may then be subsequently modified by reaction of at least one of the double bonds of the polymer with a modifying substance, for example hydrogen.
    Type: Grant
    Filed: May 6, 1999
    Date of Patent: July 30, 2002
    Assignee: Kabushiki Kaisha Toyota Chuo Kenkyusho
    Inventors: Mitsuru Nakano, Arimitsu Usuki, Qing Yao
  • Patent number: 6423818
    Abstract: The present invention includes photocurable, liquid polymers incorporating coumarin ester endgroups into their molecular structure, which polymers are crosslinked upon irradiation with ultraviolet light by photochemically allowed [2+2] cycloaddition reactions among the chain ends, and which crosslinked polymers are useful in the preparation of medical devices, tissue engineering scaffolds, drug delivery systems and, in particular, in vivo preparation of implants in an open surgical procedure or laproscopically.
    Type: Grant
    Filed: July 26, 2000
    Date of Patent: July 23, 2002
    Inventors: Takehisa Matsuda, Manabu Mizutani, Steven Arnold
  • Patent number: 6420513
    Abstract: An aliphatic polyester is provided which is manufactured by a process comprising a step of hydrolyzing cellulose so as to form D-glucose, a step of forming gluconolactone represented by the formula (II) from the D-glucose, and a step of performing ring-opening polymerization of the gluconolactone so as to form an aliphatic polyester represented by the formula (I). In the formulas above, R represents a hydrogen atom, an acetyl group, or a linear or a branched alkyl group having 1 to 3 carbon atoms, and the subscript n is an integer of 10 to 6,000.
    Type: Grant
    Filed: January 29, 2001
    Date of Patent: July 16, 2002
    Assignee: Canon Kabushiki Kaisha
    Inventor: Masato Minami
  • Patent number: 6420048
    Abstract: High molecular weight copolyesters have been prepared from macrocyclic oligoesters and cyclic esters in the presence of a transesterification catalyst. The invention generally features a method of making a copolyester, a method of making a block copolymer of copolyester, and a copolyester prepared from macrocyclic oligoesters and cyclic esters.
    Type: Grant
    Filed: June 5, 2001
    Date of Patent: July 16, 2002
    Assignee: Cyclics Corporation
    Inventor: Yi-Feng Wang
  • Publication number: 20020086971
    Abstract: Copolymers of lactide and glycolide with high glycolide content. The average glycolate block length is less then about 3, which allows the copolymer to be soluble in slightly polar solvents such as methylene chloride.
    Type: Application
    Filed: February 1, 2002
    Publication date: July 4, 2002
    Inventor: Chiem V. Pham
  • Patent number: 6376643
    Abstract: This invention relates to a method of polymerization of lactide or glycolide (GA) monomers and in particular to a method of polymerizing one type of the monomers or two types of the monomers using alkyl aluminum catalyst to proceed with bulk or solution polymerization to prepare biodegradable homopolymers or copolymers, and high-molecular-weight homopolymers of polylactide (PLA), polyglycolide (PGA), or copolymers of lactide/glycolide prepared thereof.
    Type: Grant
    Filed: November 8, 2000
    Date of Patent: April 23, 2002
    Assignee: Invigor Biotechnology Co., Ltd.
    Inventors: Wen Chung Chang, Wei-Hsiang Sun
  • Patent number: 6362308
    Abstract: Copolymers of lactide and glycolide with high glycolide content. The average glycolate block length is less then about 3, which allows the copolymer to be soluble in slightly polar solvents such as methylene chloride.
    Type: Grant
    Filed: August 10, 2000
    Date of Patent: March 26, 2002
    Assignee: Alkermes Controlled Therapeutics Inc. II
    Inventor: Chiem V. Pham
  • Patent number: 6355772
    Abstract: A nonwoven fabric comprised of a lactide polymer. The lactide polymer comprises a plurality of poly(lactide) polymer chains, residual lactide in concentration of less than about 2 percent and water in concentration of less than about 2000 parts-per-million. A process for manufacturing a nonwoven fabric with the lactide polymer composition is also disclosed.
    Type: Grant
    Filed: May 9, 2000
    Date of Patent: March 12, 2002
    Assignee: Cargill, Incorporated
    Inventors: Patrick R. Gruber, Jeffrey J. Kolstad, Christopher M. Ryan, Robin S. Eichen Conn, Eric S. Hall
  • Patent number: 6353030
    Abstract: A polylactide in a purified state, which meets the requirements of the color strengths of reference solutions B2-B9 of the brown color test of the European Pharmacopoeia, 2nd Edition (1980) part I, Section V, 6.2 and containing one or more metals in cationic form, the metal ion(s) having a concentration of at most 10 ppm. The polylactide is especially suitable for use as microparticles or implants, and contains preferably a hydrophilic drug, like octreotide or a lipophilic drug like bromocriptine.
    Type: Grant
    Filed: June 3, 1998
    Date of Patent: March 5, 2002
    Assignee: Novartis AG
    Inventor: Walter Prikoszovich
  • Publication number: 20020026031
    Abstract: The present inventors has its objects to provide a polymerization catalyst component, a copper compound which can easily be synthesized and is stable.
    Type: Application
    Filed: February 12, 2001
    Publication date: February 28, 2002
    Applicant: Sekisui Chemical Co., LTD
    Inventor: Koichi Shibayama
  • Patent number: 6346599
    Abstract: Lactone copolymers are disclosed which are polymerized from a first lactone monomer and a second amorphous monomer which is effective to suppress the crystallization of the copolymer. It is disclosed that suppression of the crystallization can provide enhanced mechanical properties in films made from the copolymers. As a result, films prepared from the copolymers of the present invention can have properties rendering them suitable for use as biodegradable trash bags as well as for other uses.
    Type: Grant
    Filed: May 10, 2000
    Date of Patent: February 12, 2002
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Daniel Goldberg, Sandra A. Kupperblatt, Robert F. Eaton, Wong F Ark, David M Simpson
  • Patent number: 6326459
    Abstract: The invention relates to a composition based on a grafted metal oxide, its preparation and its use in a process of polymerization by opening oxygenated rings such as alkyl oxides, cyclic esters or cyclic carbonates. The composition comprises a support chosen from the group of metal oxides capable of containing hydroxyl functions, onto which is grafted a group of formula (1) —M(OR)n in which M is an element chosen from scandium, zirconium, hafnium, niobium, tantalum, rare-earth metals and actinides, R is an organic group and n is an integer greater than or equal to 1. The composition is prepared by forming a suspension of the abovementioned support and then placing in contact and reacting this suspension with a compound of formula (2) M(OR)n+1 in which M, R and n are defined as above.
    Type: Grant
    Filed: July 23, 2000
    Date of Patent: December 4, 2001
    Assignee: Rhodia Chimie
    Inventors: Christelle Delaite, Thierry Hamaide, Roger Spitz, Karine Tortosa
  • Patent number: 6326458
    Abstract: A process for the continuous production of substantially purified lactide and lactide polymers from lactic acid or an ester of lactic acid including the steps of forming crude polylactic acid, preferably in the presence of a catalyst means in the case of the ester of lactic acid, to form a condensation reaction by-product and polylactic acid, and depolymerizing the polylactic acid in a lactide reactor to form crude lactide, followed by subsequent purification of the crude lactide in a distillation system. A purified lactide is then polymerized to form lactide polymers.
    Type: Grant
    Filed: October 7, 1993
    Date of Patent: December 4, 2001
    Assignee: Cargill, Inc.
    Inventors: Patrick Richard Gruber, Eric Stanley Hall, Jeffrey John Kolstad, Matthew Lee Iwen, Richard Douglas Benson, Ronald Leo Borchardt
  • Patent number: 6316590
    Abstract: Isotactic poly ((R)-lactic acid) or isotactic poly (S)-lactic acid are respectively prepared from (R,R)-lactide and (S,S)-lactide using a catalyst which has a zinc center or a magnesium center and two ligands where one of the ligands is a propagating group and the other of the ligands is not a propagating group. Heterotactic poly(lactic acid) is prepared from rac-lactide using a catalyst which has a zinc center and two ligands where one of the ligands is a propagating group and the other of the ligands is not a propagating group; heterotactic poly(lactic acid) is a novel composition. The catalyst with a magnesium center is a novel catalyst.
    Type: Grant
    Filed: November 8, 2000
    Date of Patent: November 13, 2001
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Geoffrey W. Coates, Ming Cheng, Bradley M. Chamberlain
  • Patent number: 6297350
    Abstract: Copolyesters are prepared using cyclic esters or carbonates as monomers and a metallic salt of the formula Me2+X2 as catalyst. Me2+ represents Ca, Fe(II), Mg, Mn(II) or Zn, and X is an anion of an aminocarboxylic acid, hydroxycarboxylic acid or a halide. Monomer and catalyst are used in a monomer/catalyst ratio of greater than 100.
    Type: Grant
    Filed: February 15, 2000
    Date of Patent: October 2, 2001
    Assignee: Ferring GmbH
    Inventors: Hans R. Kricheldorf, Ingrid Kreiser-Saunders, Dirk-Olaf Damrau
  • Patent number: 6277951
    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: July 13, 1999
    Date of Patent: August 21, 2001
    Assignee: Cargill, Incorporated
    Inventors: Patrick Richard Gruber, Eric Stanley Hall, Jeffrey John Kolstad, Matthew Lee Iwen, Richard Douglas Benson, Ronald Leo Borchardt
  • Patent number: 6221977
    Abstract: The present invention provides a process for preparing biodegradable aliphatic polyester grafted with polyether which comprises a step of ring opening polymerization of a hydrophilic monomer of epoxide-substituted ethyleneglycolmethylether oligomer or ethyleneglycol oligomer, and a biocompatible cyclic monomer forming polymer backbone with the said monomer, and a non-toxic biodegradable polymer prepared therefrom. In accordance with the invention, the graft ratio and molecular weight of polyether in the biodegradable aliphatic polyester can be easily controlled, and the hydrophlicity and crystallinity are also regulated thereby. The biodegradable polymer of the invention has features of minimized protein adhesion and superior softness, due to its hydrophilic side-chain. Accordingly, it can be applied as biomedical polymers such as the matrices for drug delivery system, suture thread, or bioabsorbable and water-soluble polymers.
    Type: Grant
    Filed: September 27, 1999
    Date of Patent: April 24, 2001
    Assignee: Korea Advanced Institute of Science nad Technology
    Inventors: Jung-Ki Park, Kuk Young Cho, Chang-Hyeon Kim
  • Patent number: 6207792
    Abstract: An amorphous film comprised of a lactide polymer. The lactide polymer comprises a plurality of poly(lactide) polymer chains, residual lactide in concentration of less than about 2 percent and water in concentration of less than about 2000 parts-per-million. A process for manufacturing an amorphous film with the lactide polymer composition is also disclosed.
    Type: Grant
    Filed: July 27, 1999
    Date of Patent: March 27, 2001
    Assignee: Cargill, Incorporated
    Inventors: Patrick Richard Gruber, Jeffrey John Kolstad, Christopher M. Ryan, Eric Stanley Hall, Robin Sue Eichen Conn
  • Patent number: 6206908
    Abstract: Absorbable copolymers are fabricated from the random polymerization of 1,4 dioxane-2-one and 1,3 dioxane-2-one monomers. The copolymers are useful in forming surgical articles, including both monofilament and multifilament sutures.
    Type: Grant
    Filed: May 3, 1999
    Date of Patent: March 27, 2001
    Assignee: United States Surgical Corporation
    Inventor: Mark S. Roby
  • Patent number: 6160199
    Abstract: The present invention relates to biodegradable PHA copolymers comprising at least two randomly repeating monomer units. The present invention further relates to a plastic article comprising a biodegradable copolymer, wherein the biodegradable copolymer comprises at least two randomly repeating monomer units (RRMU) wherein the first RRMU has the structure ##STR1## wherein R.sup.1 is H, or C.sub.1 or C.sub.2 alkyl, and n is 1 or 2; the second RRMU has the structure ##STR2## and wherein at least 50% of the RRMUs have the structure of the first RRMU. The present invention further relates to an absorbent article comprising a liquid pervious topsheet, a liquid impervious backsheet comprising a film comprising a PHA of the present invention and an absorbent core positioned between the topsheet and the backsheet.
    Type: Grant
    Filed: December 21, 1998
    Date of Patent: December 12, 2000
    Assignee: The Procter & Gamble Company
    Inventor: Isao Noda
  • Patent number: 6143863
    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: May 11, 1999
    Date of Patent: November 7, 2000
    Assignee: Cargill, Incorporated
    Inventors: Patrick Richard Gruber, Jeffrey John Kolstad, Eric Stanley Hall, Robin Sue Eichen Conn, Christopher M. Ryan
  • Patent number: 6114496
    Abstract: A process for preparing a biodegradable resin composition, comprising: providing a reaction mixture comprising at least one hydroxycarboxylic acid and, as a polymerization catalyst, a monoorganotin derivative; heating and stirring the reaction mixture, wherein the heating and stirring step is carried out under a reduced pressure to cause condensation polymerization or carried out in an organic solvent to cause azeotropic dehydrating polymerization. Also disclosed in a biodegradable resin composition prepared by the process.
    Type: Grant
    Filed: August 6, 1999
    Date of Patent: September 5, 2000
    Assignee: Nishikawa Rubber Co., Ltd.
    Inventors: Junzo Otera, Toru Yano, Nobuyuki Sakuda
  • Patent number: 6096855
    Abstract: The invention relates to a process for the polymerization or copolymerization of cyclic lactones of hydroxy acids by using as catalysts organometallic iron compounds containing iron salts or iron esters of carboxylic acids having at maximum 18 carbon atoms or some iron complexes. The invention relates preferably to the polymerization of lactide by using an iron acetate catalyst or initiator.
    Type: Grant
    Filed: May 27, 1999
    Date of Patent: August 1, 2000
    Assignee: Fortum Oil and Gas OY
    Inventors: Anders Sodergard, Mikael Stolt
  • Patent number: 6077931
    Abstract: The present invention relates to biodegradable PHA copolymers comprising at least two randomly repeating monomer units. The present invention further relates to a plastic article comprising a biodegradable copolymer, wherein the biodegradable copolymer comprises at least two randomly repeating monomer units (RRMU) wherein the first RRMU has the structure ##STR1## wherein R.sup.1 is H, or C.sub.1 or C.sub.2 alkyl, and n is 1 or 2; the second RRMU has the structure ##STR2## and wherein at least 50% of the RRMUs have the structure of the first RRMU. The present invention further relates to an absorbent article comprising a liquid pervious topsheet, a liquid impervious backsheet comprising a film comprising a PHA of the present invention and an absorbent core positioned between the topsheet and the backsheet.
    Type: Grant
    Filed: December 21, 1998
    Date of Patent: June 20, 2000
    Assignee: The Procter & Gamble Company
    Inventor: Isao Noda
  • Patent number: 6060582
    Abstract: Hydrogels of polymerized and crosslinked macromers comprising hydrophilic oligomers having biodegradable monomeric or oligomeric extensions, which biodegradable extensions are terminated on free ends with end cap monomers or oligomers capable of polymerization and cross linking are described. The hydrophilic core itself may be degradable, thus combining the core and extension functions. Macromers are polymerized using free radical initiators under the influence of long wavelength ultraviolet light, visible light excitation or thermal energy. Biodegradation occurs at the linkages within the extension oligomers and results in fragments which are non-toxic and easily removed from the body. Preferred applications for the hydrogels include prevention of adhesion formation after surgical procedures, controlled release of drugs and other bioactive species, temporary protection or separation of tissue surfaces, adhering of sealing tissues together, and preventing the attachment of cells to tissue surfaces.
    Type: Grant
    Filed: August 4, 1998
    Date of Patent: May 9, 2000
    Assignee: The Board of Regents, The University of Texas System
    Inventors: Jeffrey A. Hubbell, Chandrashekhar P. Pathak, Amarpreet S. Sawhney, Neil P. Desai, Jennifer L. Hill-West
  • Patent number: 6042820
    Abstract: Copolymers designed for use as particulate carriers containing functionalizable amino subunits for coupling with targeting ligand are described. The copolymers are polyesters composed of .alpha.-hydroxy acid subunits such as D, L-lactide and .alpha.-amino acid subunits such as serine or in the preferred embodiment, terpolymers of D,L-lactide and glycolide and .alpha.-amino acid subunits such as serine. Stable vaccine preparations useful as delayed release formulations containing antigen(s) or antigen(s) and co-adjuvants encapsulated within or physically mixed with ploymeric microparticles are described. The particulate carriers are useful for delivering agents to the immune system of a subject by mucosal or parenteral routes to produce immune responses, including antibody responses.
    Type: Grant
    Filed: December 20, 1996
    Date of Patent: March 28, 2000
    Assignee: Connaught Laboratories Limited
    Inventors: Kenneth K. Sokoll, Pele Chong, Michel H. Klein
  • Patent number: 6031069
    Abstract: A resorbable polymer suitable for producing a medical product, comprising a triblock terpolymer with a structure ABA formed from a biodegradable hard segment A and a biodegradable soft segment B, has as the soft segment a statistical terpolymer with a completely amorphous structure. A process for its production comprises chemically reacting the hard segment monomer with hydroxy terminal groups of the soft segment B. The resorbable medical product produced from the triblock terpolymer can be a textile fabric, produced from multifilaments, a film, membrane or an injection molding.
    Type: Grant
    Filed: October 8, 1997
    Date of Patent: February 29, 2000
    Assignee: Duetsche Institute fuer Textil- und Faserforschung Stuttgart Stiftung des oeffentlichem Rechts
    Inventors: Sven Oberhoffner, Heinrich Planck
  • Patent number: 6005067
    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 28, 1998
    Date of Patent: December 21, 1999
    Assignee: Cargill Incorporated
    Inventors: Patrick Richard Gruber, Eric Stanley Hall, Jeffrey John Kolstad, Matthew Lee Iwen, Richard Douglas Benson, Ronald Leo Borchardt
  • Patent number: 5981694
    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: November 7, 1997
    Date of Patent: November 9, 1999
    Assignee: Cargill, Incorporated
    Inventors: Patrick Richard Gruber, Jeffrey John Kolstad, Eric Stanley Hall, Robin Sue Eichen Conn, Christopher M. Ryan
  • Patent number: 5969089
    Abstract: A bulk extrusion polymerization process to derive an aliphatic polyester from a suitable ester monomer, preferably .epsilon.-caprolactone. Novel reaction formulations containing less than 100 ppm water and having an acid value less than 0.5 mg KOH/g and preferably less than 0.2 mg KOH/g enable the polymerization of bulk monomer in an extruder in a resident time of less than 2 minutes. Different catalyst and initiator systems, processing protocols, and screw configurations lead to the preferred manufacture of poly(.epsilon.-caprolactone) polymer of number average molecular weight, M.sub.n, greater than 100,000. A novel poly(.epsilon.-caprolactone) intermediate optionally grafted to starch, is described which has significantly different processing and use characteristics as compared to a straight-chain polycaprolactone.
    Type: Grant
    Filed: September 8, 1997
    Date of Patent: October 19, 1999
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Ramani Narayan, Mohan Krishnan, Joseph B. Snook, Ajay Gupta, Philippe DuBois
  • Patent number: 5952455
    Abstract: The present invention provides a process for producing polyhydroxycarboxylic acids which have a weight-average molecular weight of 50,000 or above and which are excellent as biodegradable plastics by polycondensing hydroxycarboxylic acids or oligomers thereof in the presence of an inorganic solid acid catalyst in combination with an alkali metal or an alkaline earth metal.
    Type: Grant
    Filed: October 10, 1997
    Date of Patent: September 14, 1999
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Norio Yanagisawa, Toshikazu Murayama, Yorozu Yokomori, Yoshiharu Kimura, Nobuko Tsuzaki
  • Patent number: 5906783
    Abstract: A bulk extrusion polymerization process to derive an aliphatic polyester from a suitable ester monomer, preferably .epsilon.-caprolactone. Novel reaction formulations containing less than 100 ppm water and having an acid value less than 0.5 mg KOH/g and preferably less than 0.2 mg KOH/g enable the polymerization of bulk monomer in an extruder in a resident time of less than 2 minutes. Different catalyst and initiator systems, processing protocols, and screw configurations lead to the preferred manufacture of poly(.epsilon.-caprolactone) polymer of number average molecular weight, M.sub.n, greater than 100,000. A novel poly(.epsilon.-caprolactone) intermediate optionally grafted to starch, is described which has significantly different processing and use characteristics as compared to a straight-chain polycaprolactone.
    Type: Grant
    Filed: September 8, 1997
    Date of Patent: May 25, 1999
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Ramani Narayan, Mohan Krishnan, Joseph B. Snook, Ajay Gupta, Philippe DuBois
  • Patent number: 5886093
    Abstract: The invention relates to a method for preparing a biodegradable aliphatic polyester, which comprises polymerization of a precursor of the polyester in the presence of a polyesterification catalyst in an amount of up to 0.1% by weight, based on the weight of the cyclic precursor, and a co-catalyst comprising glycerol or butyrolactone in a weight proportion of not more than three times that of the catalyst.The invention also relates to the use of the resulting biodegradable aliphatic polyester in polymer processing, such as injection molding or compression/press molding.
    Type: Grant
    Filed: May 28, 1998
    Date of Patent: March 23, 1999
    Assignee: Kabushiki Kaisha Kobe Seiko Sho
    Inventors: Martin Thomas Davies, Naseer Mohammed Qureshi, Barry Woodfine, Barry Keane
  • Patent number: 5882787
    Abstract: A poly-.epsilon.-caprolactone film whose weight-average molecular mass is equal to at least 75,000 g/mol having a modulus in tension of at least 600 MPa in the transverse and longitudinal direction and a shrinkage not exceeding 1% in both directions below the poly-.epsilon.-caprolactone melting zone. The process for producing the poly-.epsilon.-caprolactone film comprises online extrusion of the poly-.epsilon.-caprolactone through a die having a temperature not exceeding 160.degree. C. immediately following its polymerization using aluminum trialkoxide as initiator. The films according to the invention are suitable for producing films for packaging, for the protection of produce or for diapers.
    Type: Grant
    Filed: November 19, 1996
    Date of Patent: March 16, 1999
    Assignee: Solvay (Societe Anonyme)
    Inventors: Ivan Claeys, Claude Dehennau
  • Patent number: 5883222
    Abstract: The present invention provides a process for producing polyhydroxycarboxylic acids having a weight-average molecular weight of 50,000 or above which are excellent as biodegradable plastics by subjecting Lactides to ring-opening polymerization in the presence of an inorganic solid acid catalyst carrying silica and/or a light metal.
    Type: Grant
    Filed: June 3, 1997
    Date of Patent: March 16, 1999
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Norio Yanagisawa, Toshikazu Murayama, Nobuko Tsukazi, Yorozu Yokomori
  • Patent number: 5854384
    Abstract: A process for preparing poly-.alpha.-amino acid particles comprising polymerizing an .alpha.-amino acid-N-carboxy anhydride using a polymerization initiator in an organic solvent in which both the solubility of the .alpha.-amino acid-N-carboxy anhydride and the solubility of the produced poly-.alpha.-amino acid are 0.1 g/100 ml or less at 25.degree. C. Polyamino acid particles having a high molecular weight and a small bulk specific gravity can be manufactured very easily without requiring specific procedures. The polyamino acid particles can be used as a coating material for papers, resins, rubbers, and fibers; particles for cosmetics; particles for diagnostic drugs; fillers for chromatography; and an encapsulating material for drugs, fertilizers, and perfumes.
    Type: Grant
    Filed: September 25, 1996
    Date of Patent: December 29, 1998
    Assignee: SR Corporation
    Inventors: Kyoko Kuroda, Masayuki Hattori, Yoshitaka Yamakawa, Kenya Makino, Toshio Hayashi
  • Patent number: 5854383
    Abstract: Absorbable, segmented copolymers of aliphatic polyesters based on lactone monomers glycolide, trimethylene carbonate and .epsilon.-caprolactone are described. The segmented copolymers exhibit a broad range of properties, especially high strength, low modulus and fast in vivo absorption, useful in a variety of medical devices. The copolymers of the present invention have such properties, making them useful in medical devices for plastic surgery indications.
    Type: Grant
    Filed: October 6, 1997
    Date of Patent: December 29, 1998
    Assignee: Ethicon, Inc.
    Inventors: Modesto Erneta, Idrish A. Vhora
  • Patent number: 5852166
    Abstract: A lactide polymer coating resulting in a strong, repulpable, high gloss, paper coating. The lactide polymer comprises a plurality of poly(lactide) polymer chains, residual lactide in concentration of less than about 5 percent and water in concentration of less than about 2000 parts-per-million. A process for coating paper with the lactide polymer composition is also disclosed.
    Type: Grant
    Filed: July 14, 1997
    Date of Patent: December 22, 1998
    Assignee: Cargill, Incorporated
    Inventors: Patrick Richard Gruber, Jeffrey John Kolstad, Christopher M. Ryan, Eric Stanley Hall, Robin Sue Eichen Conn
  • Patent number: 5844068
    Abstract: A process for the preparation of a readily hydrolyzable and/or biodegradable polyhydroxycarboxylic acid resin which can be used in agricultural materials, gardening materials, fishery materials, caking materials, medical instruments and materials, etc. and, even when discarded after use, which undergoes hydrolysis and/or is biodegraded into carbon dioxide, water, etc. Also disclosed are a hydrolyzable and/or biodegradable polyhydroxycarboxylic acid resin composition having an increased resin strength and melt viscosity, and a process for the preparation thereof.
    Type: Grant
    Filed: March 12, 1997
    Date of Patent: December 1, 1998
    Assignee: Nishikawa Rubber Co., Ltd.
    Inventors: Junzo Otera, Toru Yano, Hirokazu Yamamoto, Nobuyuki Sakuda
  • Patent number: 5840811
    Abstract: An optically active block polyester copolymer formed of structural units represented by the following general formulas (I) and (II): ##STR1## wherein represents for an asymmetric carbon atom and m and n each represents a natural number in the range of from 300 to 5000 is obtained by subjecting an optically active butyrolactone and a species of lactone other than the optically active butyrolactone to sequential ringopening copolymerization in the presence of a catalyst. This optically active block polyester copolymer possesses a high molecular weight and a high melting point (not less than 130.degree. C.) and forms a biodegradable and hydrolyzable material of high strength capable of tolerating the impacts of actual use.
    Type: Grant
    Filed: January 22, 1997
    Date of Patent: November 24, 1998
    Assignee: Takasago International Corporation
    Inventors: Yoji Hori, Tohru Kobayashi, Hideyuki Hongo, Akio Yamaguchi, Yoko Takahashi, Takashi Imai, Toshimitsu Hagiwara
  • Patent number: 5834567
    Abstract: Disclosed are a biodegradable copolymer and a biodegradable article molded therefrom, said copolymer having a number average molecular weight ranging from 1,000 to 1,000,000 consisting essentially of (A) from 5 to 99% by mol of epsilon-caprolactone or delta-valerolactone structural units and (B) from 95 to 1% by mol of oxetane structural units, said structural units being combined in the state of a block, and containing an organic aluminum-based Lewis acid represented by general formula (I) ##STR1## wherein R is an alkyl group having a carbon number ranging from 1 to 4, Y is independently selected from a substituted group, and p is any one of 1, 2 and 3. Also disclosed are block polymers of lactone and dimethyltrimethylene carbonate and blends of polylactone with polyoxetane.
    Type: Grant
    Filed: February 18, 1997
    Date of Patent: November 10, 1998
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Hajime Yasuda
  • Patent number: 5821327
    Abstract: The polymerization reaction is conducted by heating a lactide, a cyclic imide compound (e.g. succinimide, etc.) and a polymerization catalyst (e.g. tin octylate, etc.) at 100-190.degree. C. with stirring under a nitrogen gas flow. It is preferred that an amount of the cyclic imide compound is from 1 to 35% by mole based on the lactide. Even if an amount of the polymerization catalyst is small, e.g. 0.00001-0.1 mole %, based on the lactide, polylactic acid can be efficiently prepared. It is possible to avoid remains of the catalyst in the polymer and coloring of the polymer.
    Type: Grant
    Filed: March 17, 1997
    Date of Patent: October 13, 1998
    Assignee: Shimadzu Corporation
    Inventors: Masaaki Oota, Masahiro Ito
  • Patent number: 5801224
    Abstract: A bulk extrusion polymerization process to derive an aliphatic polyester from a suitable ester monomer, preferably .epsilon.-caprolactone. Novel reaction formulations containing less than 100 ppm water and having an acid value less than 0.5 mg KOH/g and preferably less than 0.2 mg KOH/g enable the polymerization of bulk monomer in an extruder in a resident time of less than 2 minutes. Different catalyst and initiator systems, processing protocols, and screw configurations lead to the preferred manufacture of poly(.epsilon.-caprolactone) polymer of number average molecular weight, M.sub.n, greater than 100,000. A novel poly(.epsilon.-caprolactone) intermediate optionally grafted to starch, is described which has significantly different processing and use characteristics as compared to a straight-chain polycaprolactone.
    Type: Grant
    Filed: April 26, 1996
    Date of Patent: September 1, 1998
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Ramani Narayan, Mohan Krishnan, Joseph B. Snook, Ajay Gupta, Philippe DuBois
  • Patent number: 5798435
    Abstract: A composition comprising a polylactide polymer with improved extensional viscosity and methods of making the same are disclosed. The polylactide polymer composition is prepared by providing in the composition polylactide polymer molecules which have been modified, relative to linear non-substituted polylactide, to provide increased molecular interaction among polylactide backbone chains in the composition. The preferred polylactide polymer composition has a number average molecular weight of at least about 10,000 (preferably at least 50,000) and a polydispersity of at least about 2.5. In addition, the polylactide polymer composition should have a neck-in ratio of less than about 0.8.
    Type: Grant
    Filed: September 3, 1996
    Date of Patent: August 25, 1998
    Assignee: Cargill, Incorporated
    Inventors: Patrick Richard Gruber, Jeffrey John Kolstad, David Roy Witzke, Mark Henry Hartmann, Andrea Lee Brosch
  • Patent number: 5798436
    Abstract: An amorphous film comprised of a lactide polymer. The lactide polymer comprises a plurality of poly(lactide) polymer chains, residual lactide in concentration of less than about 2 percent and water in concentration of less than about 2000 parts-per-million. A process for manufacturing an amorphous film with the lactide polymer composition is also disclosed.
    Type: Grant
    Filed: September 5, 1996
    Date of Patent: August 25, 1998
    Assignee: Cargill, Incorporated
    Inventors: Patrick Richard Gruber, Jeffrey John Kolstad, Christopher M. Ryan, Eric Stanley Hall, Robin Sue Eichen Conn
  • Patent number: 5773563
    Abstract: Crystane, low melting .epsilon.-Caprolactone polymers which undergo accelerated hydrolysis, and their use as lubricant coatings and/or as coatings containing bioactive agents, as carriers of viable cells, and as coatings for open-cell microporous template or constucts for tissue regeneration; the polymers bearing basic functionalities can be linked ionically or covalently to the ester chain which induces autocatalyzed hydrolysis.
    Type: Grant
    Filed: June 3, 1996
    Date of Patent: June 30, 1998
    Assignee: Poly-Med, Inc.
    Inventor: Shalaby W. Shalaby
  • Patent number: 5770682
    Abstract: A method for producing a polylactic acid, comprising the steps of carrying out a ring-opening polymerization of lactide to give polylactic acid, adding a compound capable of inactivating a catalyst for ring-opening polymerization of the lactide at the completion of the reaction, and removing unchanged lactide from the polylactic acid product by reducing pressure and/or allowing an inert gas to pass; and a method for forming fiber or film directly from the polylactic acid produced by the invention.
    Type: Grant
    Filed: July 11, 1996
    Date of Patent: June 23, 1998
    Assignee: Shimadzu Corporation
    Inventors: Hitomi Ohara, Seiji Sawa, Masahiro Ito, Yasuhiro Fujii, Masaaki Oota, Hideshi Yamaguchi
  • Patent number: 5770683
    Abstract: A preparation process of polyhydroxycarboxylic acid comprising conducting dehydration polycondensation of hydroxycarboxylic acid or an oligomer of the same in a reaction mixture containing said hydroxycarboxylic acid or the oligomer of the same and an organic solvent substantially in the absence of water to give polyhydroxycarboxylic acid having an weight average molecular weight of 50,000 or more, successively mixing the reaction mixture containing said polyhydroxycarboxylic acid with at least one binder selected from the group consisting of (1) polyisocyanate compound, (2) polybasic acid anhydride, (3) cyclic imino ester, (4) cyclic imino ether, (5) aromatic hydroxycarboxylic acid, (6) polyamino compound, (7) polyhydric alcohol, (8) epoxy compound, (9) polyfunctional aziridine compound, (10) lactam, (11) lactone, and (12) diethylene glycol bischloroforate, and reacting to obtain polyhydroxycarboxylic acid having a weight average molecular weight of 100,000 or more the polyhydroxycarboxylic acid which is obt
    Type: Grant
    Filed: October 20, 1995
    Date of Patent: June 23, 1998
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Yasunori Yoshida, Michihiko Miyamoto, Shoji Obuchi, Kan Ideda, Masahiro Ohta
  • Patent number: 5763564
    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: March 29, 1996
    Date of Patent: June 9, 1998
    Assignee: Cargill, Incorporated
    Inventors: Patrick Richard Gruber, Jeffrey John Kolstad, Eric Stanley Hall, Robin Sue Eichen Conn, Christopher M. Ryan