Polymerizing In The Presence Of A Specified Material Other Than A Reactant Patents (Class 528/355)
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Publication number: 20020026031Abstract: The present inventors has its objects to provide a polymerization catalyst component, a copper compound which can easily be synthesized and is stable.Type: ApplicationFiled: February 12, 2001Publication date: February 28, 2002Applicant: Sekisui Chemical Co., LTDInventor: Koichi Shibayama
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Patent number: 6346599Abstract: 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: GrantFiled: May 10, 2000Date of Patent: February 12, 2002Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Daniel Goldberg, Sandra A. Kupperblatt, Robert F. Eaton, Wong F Ark, David M Simpson
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Patent number: 6346592Abstract: A procedure for preparing compact and spherical self-activated polymer particles of vinyl monomers having a narrow or monodisperse size distribution in accordance with a special precipitation polymerization process in a polar organic medium, possibly in an organic polar medium mixed with water. The medium is a good solvent for the monomer and a poor solvent for the polymer. All ingredients are initially dissolved in the medium and when polymerization has been initiated, formed polymer precipitates from solution and by the aid of the dispersion stabiliser the polymer particles are kept apart as free spherical beads. The polymerization takes place with a temperature profile which produces a scattered chain length distribution, increases the conversion speed and reduces the particle size distribution. The method for producing the particles also achieves an increased degree of freedom for the production of particles with a certain particle size in a given conversion time.Type: GrantFiled: August 26, 1999Date of Patent: February 12, 2002Assignee: Norsk Hydro ASAInventors: Bård Sæthre, Steinar Pedersen
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Patent number: 6326459Abstract: 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: GrantFiled: July 23, 2000Date of Patent: December 4, 2001Assignee: Rhodia ChimieInventors: Christelle Delaite, Thierry Hamaide, Roger Spitz, Karine Tortosa
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Patent number: 6323307Abstract: The present invention is directed to a method for reducing waste accumulation by using an environmentally degradable disposable material. The disposable material, which includes a hydroxycarboxylic acid-containing polymer, degrades hydrolytically during operative and disposal stages in a controlled manner such that the disposal degradation rate of the material is accelerated relative to the operative degradation rate of the material.Type: GrantFiled: August 16, 1995Date of Patent: November 27, 2001Assignee: Cargill Dow Polymers, LLCInventors: Donald M. Bigg, Richard G. Sinclair, Edward S. Lipinsky, John H. Litchfield, Billy R. Allen
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Patent number: 6294646Abstract: The present invention is a water-responsive blend of a polylactide and a polyvinyl alcohol. The present invention includes films and personal care articles comprising a blend of a polyvinyl alcohol and a polylactide and includes a method of making such films and articles and a method of varying the water responsiveness of such films and articles. In a preferred embodiment, the compositions, films and articles comprise a blend of polyvinyl alcohol and modified polylactide. The compositions and films described herein are useful as a component in flushable and degradable articles.Type: GrantFiled: March 14, 2000Date of Patent: September 25, 2001Assignee: Kimberly-Clark Worldwide, Inc.Inventors: James H. Wang, David M. Schertz
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Patent number: 6291077Abstract: A lactone chain-extended polyester polyol of the present invention comprises the reaction product of a lactone and a previously chain-extended phenolic-based hydroxyl compound. The previously chain-extended phenolic-based hydroxyl compound may comprise the reaction product of (i) a lactone or an alkoxylating agent selected from the group consisting of alkylene oxides and alkylene carbonates, and (ii) a phenolic aralkylation polymer comprising the reaction product of a phenolic monomer having at least two free reactive positions; a styrene derivative; and a coupling agent. The previously chain-extended phenolic-based hydroxyl compound also may be chain-extended by reacting with a lactam to produce a lactam chain-extended polyester polyamide. The polyols and polyamides of the present invention provide unique combinations of hard and soft functionalities, which translates into materials exhibiting a unique combination of toughness and hardness.Type: GrantFiled: August 28, 2000Date of Patent: September 18, 2001Assignee: Georgia-Pacific Resins, Inc.Inventors: Rajan Hariharan, David A. Hutchings, Kenneth A. Bourlier, Ellen V. Nagy
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Patent number: 6268465Abstract: An aliphatic polyester amide which is hydrolysis-resistant includes a ternary polycondensation product of monomeric constituents composed of a monomeric constituent A which is at least one diol having a general formula: HO—R1—OH, where R1 is an aliphatic residue having 2-16 carbon atoms; a monomeric constituent B which is at least one dicarboxylic acid having a general formula: HOOC—R2—COOH, where R2 is an aliphatic residue having 1-14 carbon atoms; and a monomeric constituent C which is at least one diamine having a general formula: H2N—R3—NH2, where R3 is an aliphatic residue having 2-16 carbon atoms and is present in an amount of up to about 5% by weight based on total weight of the monomeric constituents, wherein polycondensation proceeds in the presence of a catalyst comprised of constituent D, which is a metal-containing catalyst, in combination with constituent E, which is at least one of an organic phosphorus compound and an inorganic phosphorus compound, and whereiType: GrantFiled: April 12, 1999Date of Patent: July 31, 2001Assignee: BK Giulini Chemie GmbH Co OHGInventors: Gudrun Chomiakow, Hasan Ulubay, Emil Wilding
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Patent number: 6255445Abstract: Poly(lactones) are provided. The poly(lactones) are obtained by polymerization of a lactone with an initiator system comprising at least one polyfunctional initiator. The poly(lactones) have a shear viscosity at some temperature in the range of from 35 to 45° C. above the melting temperature of the poly(lactone) of at least 6 kPas at 0.1 s−1 shear rate and no greater than 3.5 kPas at 100 s−1 shear rate, and a shear viscosity activation energy of greater than 40 kJ/mol. Preferably, the poly(lactone) is poly(caprolactone).Type: GrantFiled: April 17, 1998Date of Patent: July 3, 2001Assignee: Solvay Interox LimitedInventors: Amanda Jane Dutton, Robert Craig Wasson, Ivan Lode André Maria Claeys
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Patent number: 6214967Abstract: A two-step process is described for the polymerization of lactide to polylactide, in which process in the first step polymerization is carried out to a conversion of at least 50% by weight, and in the latter step the polylactide is polymerized further to a high conversion in conditions in which the mixing of the melt and the evaporation of the lactide are avoided.Type: GrantFiled: October 13, 1999Date of Patent: April 10, 2001Assignee: Fortum Oil and Gas OyInventors: Kari Jansson, Jukka Koskinen, Johan-Fredrik Selin
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Patent number: 6174990Abstract: 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 wherein R1 is H, or C1 or C2 alkyl, and n is 1 or 2; the second RRMU has the structure 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: GrantFiled: December 21, 1998Date of Patent: January 16, 2001Assignee: The Procter & Gamble CompanyInventor: Isao Noda
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Patent number: 6166151Abstract: A lactone chain-extended polyester polyol of the present invention comprises the reaction product of a lactone and a previously chain-extended phenolic-based hydroxyl compound. The previously chain-extended phenolic-based hydroxyl compound may comprise the reaction product of (i) a lactone or an alkoxylating agent selected from the group consisting of alkylene oxides and alkylene carbonates, and (ii) a phenolic aralkylation polymer comprising the reaction product of a phenolic monomer having at least two free reactive positions; a styrene derivative; and a coupling agent. The previously chain-extended phenolic-based hydroxyl compound also may be chain-extended by reacting with a lactam to produce a lactam chain-extended polyester polyamide. The polyols and polyamides of the present invention provide unique combinations of hard and soft functionalities, which translates into materials exhibiting a unique combination of toughness and hardness.Type: GrantFiled: June 22, 1999Date of Patent: December 26, 2000Assignee: Georgia-Pacific Resins, Inc.Inventors: Rajan Hariharan, David A. Hutchings, Kenneth A. Bourlier, Ellen V. Nagy
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Patent number: 6153563Abstract: A sealed pouch of a single layer polyolefin film having a thickness of from about 0.005 to 0.001 inch and a melting point below about 280.degree. F. which is soluble in a lubricating oil base. The pouch contains a solid lithium hydroxide or lithium fatty acid salt or mixtures thereof for use in preparing greases.Type: GrantFiled: November 10, 1999Date of Patent: November 28, 2000Assignee: Lithchem InternationalInventors: W. Novis Smith, Joel McCloskey, Andrew Atterbury
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Patent number: 6143947Abstract: The present invention relates to fibers, and nonwovens comprising said fibers, comprising a biodegradable copolymer, wherein the copolymer comprises at least two randomly repeating monomer units (RRMU) wherein the first RRMU monomer unit has the structure ##STR1## and the second RRMU has the structure ##STR2## 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 biodegradable liquid impervious backsheet comprising the above fibers and/or nonwovens, and an absorbent core positioned between the topsheet and the backsheet.Type: GrantFiled: August 30, 1999Date of Patent: November 7, 2000Assignee: The Procter & Gamble CompanyInventor: Isao Noda
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Patent number: 6114496Abstract: 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: GrantFiled: August 6, 1999Date of Patent: September 5, 2000Assignee: Nishikawa Rubber Co., Ltd.Inventors: Junzo Otera, Toru Yano, Nobuyuki Sakuda
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Patent number: 6111060Abstract: 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: GrantFiled: January 2, 1998Date of Patent: August 29, 2000Assignee: Cargill, IncorporatedInventors: Patrick R. Gruber, Jeffrey J. Kolstad, Christopher M. Ryan, Robin S. Eichen Conn, Eric S. Hall
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Patent number: 6096855Abstract: 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: GrantFiled: May 27, 1999Date of Patent: August 1, 2000Assignee: Fortum Oil and Gas OYInventors: Anders Sodergard, Mikael Stolt
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Patent number: 6093464Abstract: A pressure-sensitive adhesive composition with a pressure-sensitive adhesive property and heat resistance comprises a polyester having a polylactone structure as the main chain. A pressure-sensitive adhesive sheet with a releasing property of a peelable liner and containing no silicone can be obtained by using the pressure-sensitive adhesive composition in combination with a polyolefin film without being subjected to a silicone treatment as a peelable liner. When the pressure-sensitive adhesive sheet comprises a base material having formed thereon the layer of the pressure-sensitive adhesive composition and the back side of the base material has a surface composed of a polyolefin, neither a peelable liner nor a silicone treatment is required. The pressure-sensitive adhesive sheet is suitably used for computer instruments etc., because it contains no silicone.Type: GrantFiled: May 23, 1997Date of Patent: July 25, 2000Assignee: Nitto Denko CorporationInventors: Yasuyuki Tokunaga, Masahiko Ando, Takeshi Yamanaka, Waka Hikosaka
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Patent number: 6077930Abstract: A preparation process of a polymer comprising conducting ring-opening polymerization of a 4- to 10-membered ring-opening polymerizable cyclic monomer in the presence of a phosphazenium salt of an active hydrogen compound represented by the chemical formula (1): ##STR1## wherein n is an integer of 1 to 8 and indicates the number of phosphazenium cations, Z.sup.n- is an anion of a n-valent active hydrogen compound derived by releasing n protons from an active hydrogen compound having a maximum of 8 active hydrogen atoms, a, b, c and d are individually a positive integer or 0 and are not all 0 at the same time, R's are the same or different hydrocarbons having 1 to 10 carbon atoms, and two R's located on each common nitrogen atom may be coupled together to form a ring structure; or in the presence of the phosphazenium salt of the active hydrogen compound and the active hydrogen compound is disclosed.Type: GrantFiled: May 15, 1998Date of Patent: June 20, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Tadahito Nobori, Shinji Kiyono, Takaomi Hayashi, Usaji Takaki
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Patent number: 6075118Abstract: The present invention is a water-responsive film. More particularly, the present invention is a film comprising a blend of a polyvinyl alcohol and a polylactide and a method of making such films. In a preferred embodiment, the invention is a film comprising a blend of polyvinyl alcohol and modified polylactide and a method of making such films. The films are useful as a component in flushable and degradable articles.Type: GrantFiled: July 31, 1997Date of Patent: June 13, 2000Assignee: Kimberly-Clark Worldwide, Inc.Inventors: James Hongxue Wang, David Michael Schertz, Dave Allen Soerens
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Patent number: 6060582Abstract: 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: GrantFiled: August 4, 1998Date of Patent: May 9, 2000Assignee: The Board of Regents, The University of Texas SystemInventors: Jeffrey A. Hubbell, Chandrashekhar P. Pathak, Amarpreet S. Sawhney, Neil P. Desai, Jennifer L. Hill-West
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Patent number: 6020453Abstract: Surface material for an absorbent article, wherein the material includes a surface layer which excretes lactic acid and/or an acid physiologically acceptable derivative thereof when the surface layer is immersed in a water volume, the weight ratio between surface layer and water volume being 1:100, in an amount such that the lactic acid and/or derivative excreted within a time period of at most 20 hours will impart a pH of at most 3.0 to the water volume.Type: GrantFiled: June 12, 1997Date of Patent: February 1, 2000Assignee: SCA Molnlycke Products ABInventors: Bjorn Larsson, Erik Lagerstrom
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Patent number: 6013590Abstract: The present invention relates to fibers, and nonwovens comprising said fibers, comprising a biodegradable copolymer, wherein the copolymer comprises at least two randomly repeating monomer units (RRMU) wherein the first RRMU monomer unit has the structure ##STR1## and the second RRMU has the structure ##STR2## 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 previous topsheet, a biodegradable liquid impervious backsheet comprising the above fibers and/or nonwovens, and an absorbent core positioned between the topsheet and the backsheet.Type: GrantFiled: January 29, 1996Date of Patent: January 11, 2000Assignee: The Procter & Gamble CompanyInventor: Isao Noda
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Patent number: 5990271Abstract: The present invention relates to a film comprising a biodegradable copolymer, wherein the copolymer comprises at least two randomly repeating monomer units (RRMU) wherein the first RRMU monomer unit has the structure ##STR1## and the second RRMU has the structure ##STR2## 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 biodegradable liquid impervious backsheet comprising the above film, and an absorbent core positioned between the topsheet and the backsheet.Type: GrantFiled: July 23, 1996Date of Patent: November 23, 1999Assignee: The Procter & Gamble CompanyInventor: Isao Noda
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Patent number: 5981694Abstract: 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: GrantFiled: November 7, 1997Date of Patent: November 9, 1999Assignee: Cargill, IncorporatedInventors: Patrick Richard Gruber, Jeffrey John Kolstad, Eric Stanley Hall, Robin Sue Eichen Conn, Christopher M. Ryan
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Patent number: 5939191Abstract: A gut suture is coated with a bioabsorbable copolymer obtained by polymerizing a major amount of .epsilon.-caprolactone and a minor amount of at least one other copolymerizable monomer in the presence of polyhydric alcohol as initiator. The coated gut suture can be packaged in the absence of conventional tubing fluid, i.e., in the dry state, while at the same time retaining flexibility, pliability and resistance to fray. In an alternative embodiment, a gut suture is coated with a pre-coating composition prior to being coated with the bioabsorbable copolymer.Type: GrantFiled: June 23, 1997Date of Patent: August 17, 1999Assignee: United States Surgical CorporationInventors: Steven L. Bennett, Ying Jiang, Mark S. Roby, Nagabhushanam Totakura
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Patent number: 5919893Abstract: Degradable polyesteramide suitable for use in biomedical applications is obtained by reacting diamino alkyl ester with alpha hydroxy acid to form diamide-diol which is reacted with acyl halide or dicarboxylic acid to yield polyesteramide.Type: GrantFiled: January 28, 1998Date of Patent: July 6, 1999Assignee: United States Surgical CorporationInventors: Mark S. Roby, Ying Jiang
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Patent number: 5914387Abstract: Polyesteramides having amino acid-derived groups alternating with hydroxy acid-derived groups are useful in making shaped articles, particularly, shaped articles suitable for use as surgical devices.Type: GrantFiled: January 28, 1998Date of Patent: June 22, 1999Assignee: United States Surgical CorporationInventors: Mark S. Roby, Ying Jiang
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Patent number: 5910545Abstract: Disclosed is a thermoplastic composition comprising an unreacted mixture of a poly(lactic acid) polymer; a polybutylene succinate polymer or a polybutylene succinate adipate polymer, or a mixture of such polymers; and a wetting agent. The thermoplastic composition exhibits substantial biodegradable properties yet is easily processed. The thermoplastic composition is useful in making multicomponent fibers or nonwoven structures that may be used in a disposable absorbent product intended for the absorption of fluids such as body fluids.Type: GrantFiled: October 31, 1997Date of Patent: June 8, 1999Assignee: Kimberly-Clark Worldwide, Inc.Inventors: Fu-Jya Tsai, Brian T. Etzel
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Patent number: 5902874Abstract: Cyclic monomers prepared by novel methods are useful in making polyesteramides which can be made into shaped articles, particularly, shaped articles suitable for use as surgical devices.Type: GrantFiled: January 28, 1998Date of Patent: May 11, 1999Assignee: United States Surgical CorporationInventors: Mark S. Roby, Ying Jiang
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Patent number: 5902875Abstract: A polyesteramide suitable for use in the fabrication of absorbable surgical devices such as monofilament and multifilament sutures, films, sheets, plates, clips, staples, pins, screws, and the like, is obtained by reacting a monoalkanolamine such as ethanolamine with a diacid halide such as succinic acidchloride to provide a diamidediol and thereafter reacting the diamidediol with the same or different diacid halide under polymerization conditions to form the polyesteramide.Type: GrantFiled: January 28, 1998Date of Patent: May 11, 1999Assignee: United States Surgical CorporationInventors: Mark S. Roby, Ying Jiang
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Patent number: 5889127Abstract: Disclosed is a process for the continuous preparation of a polyester-based polymer having excellent quality which is useful as materials for medical care, coatings, and wrapping. In the process for the continuous preparation, a column-type continuous reactor is essentially employed.Type: GrantFiled: May 15, 1998Date of Patent: March 30, 1999Assignee: Daicel Chemical Industries, Ltd.Inventors: Takashi Iiyama, Takashi Sato, Manabu Yamada
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Patent number: 5886093Abstract: 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: GrantFiled: May 28, 1998Date of Patent: March 23, 1999Assignee: Kabushiki Kaisha Kobe Seiko ShoInventors: Martin Thomas Davies, Naseer Mohammed Qureshi, Barry Woodfine, Barry Keane
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Patent number: 5854384Abstract: 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: GrantFiled: September 25, 1996Date of Patent: December 29, 1998Assignee: SR CorporationInventors: Kyoko Kuroda, Masayuki Hattori, Yoshitaka Yamakawa, Kenya Makino, Toshio Hayashi
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Patent number: 5780580Abstract: A crystalline polylactone is produced having reactive acrylate end groups. When incorporated into a thermosetting resin which includes reactive C.dbd.CH.sub.2 sites, the present functionalized polylactone acts as a toughener, greatly increasing the impact resistance of the final cured product. Also disclosed are carboxyl-bearing polylactones as tougheners for epoxy resin systems.Type: GrantFiled: August 15, 1997Date of Patent: July 14, 1998Assignee: Clemson UniversityInventors: Shalaby W. Shalaby, Lance A. Monroe
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Patent number: 5773562Abstract: A film having a net endotherm greater than about 10 joules per gram of polymer that contains chains including lactic acid residuals; said film further comprising; a) a melt stable polymer composition comprising at least 5% by weight of a melt stable first polymer component with lactic acid residuals b) said first polymer having a number average molecular weight of at least 40,000 and no greater than 300,000 and c) said first melt stable polymer composition having a lactide concentration of less than about 2% by weight of melt stable polymer including polymer chains with lactic acid residuals. A process for preparing a film having a net endotherm greater than about 10 joules per gram of polymer that contains chains including lactic acid residuals is also disclosed.Type: GrantFiled: February 28, 1996Date of Patent: June 30, 1998Assignee: Cargill, IncorporatedInventors: Patrick Richard Gruber, Jeffrey John Kolstad, Christopher M. Ryan, Eric Stanley Hall, Robin Sue Eichen Conn
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Patent number: 5763564Abstract: 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: GrantFiled: March 29, 1996Date of Patent: June 9, 1998Assignee: Cargill, IncorporatedInventors: Patrick Richard Gruber, Jeffrey John Kolstad, Eric Stanley Hall, Robin Sue Eichen Conn, Christopher M. Ryan
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Patent number: 5756603Abstract: The present invention provides a method capable of continuously efficiently producing a 2-hydroxycarboxylic acid oligomer while effectively removing the water contained in a raw material and the water produced by dehydration reaction. In production of a 2-hydroxycarboxylic acid oligomer by supplying a 2-hydroxycarboxylic acid to a reaction system, a dehydration system is provided between a raw material supply system and a polymerization reaction system so as to remove the water contained in the raw material and the water produced in the polymerization reaction system. As a result, the raw material in the dehydration system is concentrated and then supplied to the polymerization reaction system.Type: GrantFiled: May 20, 1997Date of Patent: May 26, 1998Assignee: Kabushiki Kaisha Kobe Seiko ShoInventors: Hiroshi Maeda, Kunihiko Shimizu, Yuji Kurishiro, Eiichi Kawada, Kazuhisa Fujisawa
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Patent number: 5747390Abstract: Absorbable/resorbable mixtures of aliphatic polyesters of poly(lactide), poly(glycolide), poly(trimethylene carbonate), poly(p-dioxanone) and poly(.epsilon.-caprolactone) and calcium containing bone regenerating compounds such as powdered, non-fibrous calcium phosphates are described. The composites when used to manufacture medical devices exhibit improved absorption characteristics and other physical properties.Type: GrantFiled: February 20, 1996Date of Patent: May 5, 1998Assignee: Ethicon, Inc.Inventors: Kevin Cooper, Chao C. Chen, Angelo Scopelianos
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Patent number: 5731406Abstract: A process for the preparation of macromonomers by reaction between a lactone and a hydroxyalkylacrylate in the presence of >200 ppm phosphoric acid catalyst is provided. The reaction takes place in the presence of a free radical inhibitor at a temperature of from 100.degree. to 130.degree. C. Preferably, the lactone is .epsilon.-caprolactone and the hydroxyalkylacrylate is selected from the group consisting of 2-hydroxyethylacrylate and 2-hydroxyethylmethacrylate.Type: GrantFiled: June 12, 1996Date of Patent: March 24, 1998Assignee: Solvay Interox LimitedInventor: Robert Craig Wasson
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Patent number: 5719256Abstract: The invention provides a novel preparation process of a polycondensation type polymer, an excellent polymer which is represented by lactic acid and the preparation process of the polymer, a polycondensation agent used for the preparation process, and an intermediate. Specifically, the invention provides a preparation process of the polycondensation type polymer, for example, polyamide, polyimide, polythioester and polyester, comprising bonding a carboxyl group comprising compound with an active hydrogen group comprising compound in the presence of haloiminium salt. The invention provides excellent polylactic acid having a controlled D/L-isomer ratio in the repeating structural units and preparation process of polylactic acid, and further provides a haloiminium salt compound used for the preparation process and an intermediate compound of acid chloride.Type: GrantFiled: October 15, 1996Date of Patent: February 17, 1998Assignee: Mitsu Toatsu Chemicals, Inc.Inventors: Shoji Tamai, Yukiko Mori, Kenichi Goto, Katsuji Watanabe, Osamu Kohgo, Kotaro Shimizu, Toshiyuki Kataoka, Takashi Kuroki, Wataru Yamashita, Hideki Mizuta, Teruyuki Nagata
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Patent number: 5710234Abstract: Ortho spiroesters of excellent heat resistance and low volume shrinkage during curing are disclosed. Resin compositions of excellent heat resistance and low curing shrinkage containing these ortho spiroesters are also provided. These photosensitive or heat-curable resin compositions are formulated from photo- or heat-polymerizable compounds containing ethylenic double bonds and carboxyl groups, photopolymerization initiators and sensitizers, or polymerization initiators which generate radicals by heat, and said ortho spiroesters. These resin compositions have low curing shrinkage and are useful for applications requiring dimensional accuracy such as molding materials, encapsulants, adhesives and coatings and also for the preparation of image-forming materials such as protective films for color filters, inks and electrically insulating spacers for touch panels.Type: GrantFiled: January 19, 1996Date of Patent: January 20, 1998Assignees: Nippon Steel Chemical Co., Ltd., Nippon Steel CorporationInventors: Koichi Fujishiro, Masaya Furukawa, Kazuhiro Watanabe, Takero Teramoto
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Patent number: 5700901Abstract: The invention relates to resorbable mouldings and processes for producing them.Type: GrantFiled: January 11, 1995Date of Patent: December 23, 1997Assignee: Boehringer Ingelheim KGInventors: Achim Hurst, Wladis Winkler-Gwienek, Berthold Buchholz, Dieter Bendix, Gunther Entenmann
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Patent number: 5691444Abstract: A crystalline polylactone is produced having reactive acrylate end groups. When incorporated into a thermosetting resin which includes reactive C.dbd.CH.sub.2 sites, the present functionalized polylactone acts as a toughener, greatly increasing the impact resistance of the final cured product. Also disclosed are carboxyl-bearing polylactones as tougheners for epoxy resin systems.Type: GrantFiled: December 6, 1995Date of Patent: November 25, 1997Assignee: Clemson UniversityInventors: Shalaby W. Shalaby, Lance A. Monroe
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Patent number: 5639851Abstract: Absorbable, segmented copolymers of aliphatic polyesters based on lactone monomers lactide, and p-dioxanone are described. The segmented copolymers exhibit a broad range of properties, especially high strength and long elongations. This unique elastomeric behavior makes the copolymers of the present invention useful in a variety of medical device applications, especially adhesion prevention barriers and hemostatic devices.Type: GrantFiled: October 2, 1995Date of Patent: June 17, 1997Assignee: Ethicon, Inc.Inventors: Rao S. Bezwada, Kevin Cooper
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Patent number: 5633342Abstract: A method is provided for the synthesis of environmentally degradable block copolymers which includes the sequential polymerization of polymer-forming materials in the presence of one or more polymerization reaction accelerants and catalysts. The accelerants are a class of hydrogen-labile compounds which act as polymerization initiators and accelerate the polymerization rate significantly. The environmentally degradable block copolymers produced include those comprising segments of polymers of alkylene oxides, trimethylene carbonates, lactones and cyclic esters of hydroxycarboxylic acids.Type: GrantFiled: October 27, 1995Date of Patent: May 27, 1997Assignee: Chronopol, Inc.Inventors: Dan W. Verser, Kevin H. Schilling, Xiaomao Chen
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Patent number: 5631344Abstract: The block copolymer of polyesters and polycarbonates comprises at least one of each of the constituting units of (I) and (II) having the general formulae: ##STR1## where the sign * indicates an asymmetric carbon atom; R.sub.1, R.sup.2, R.sup.3 and R.sup.4 are either a hydrogen atom or a methyl group; m and n are respective a natural numbers ranging from 300 to 5000: The block copolymer is obtained by successive ring-opening and copolymerization of optically active .beta.-butyrolactones and cyclic carbonates in the presence of a catalyst.The block polymer obtained has high molecular weight and high melting temperature, and can thus be used as a high strength material for practical use and which has bio-degradable and hydrolyzable nature.Type: GrantFiled: October 27, 1995Date of Patent: May 20, 1997Assignee: Takasago Koryo Kogyo Kabushiki Kaisha (Takasago International Corporation)Inventors: Hideyuki Hongo, Akio Yamaguchi, Yoji Hori, Toshimitsu Hagiwara, Yoko Takahashi
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Patent number: 5610266Abstract: The present invention relates to new copolymers of trimethylenecarbonate and optically inactive lactides, the preparation and use thereof.Type: GrantFiled: June 7, 1995Date of Patent: March 11, 1997Assignee: Boehringer Ingelheim KGInventor: Berthold Buchholz
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Patent number: 5563238Abstract: A water and UV light degradable copolymer of monomers of lactic acid and a modifying monomer selected from the class consisting of ethylene glycol, propylene glycol, P-dioxanone, 1,5 dioxepan-2-one, 1,4-oxathialan-2-one, 1,4-dioxide and mixtures thereof. These copolymers are useful for waste disposal and agricultural purposes. Also disclosed is a water degradable blend of polylactic acid or modified polylactic acid and high molecular weight polyethylene oxide wherein the high molecular weight polyethylene oxide is present in the range of from about 2 by weight to about 50% by weight, suitable for films. A method of applying an active material selected from the class of seeds, seedlings, pesticides, herbicides, fertilizers and mixtures thereof to an agricultural site is also disclosed.Type: GrantFiled: October 25, 1994Date of Patent: October 8, 1996Assignee: ARCH Development CorporationInventors: Patrick V. Bonsignore, Robert D. Coleman
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Patent number: 5492997Abstract: A copolymer of a lactone and a polycyclic carbonate is prepared by heating a monomer of a lactone with a polycyclic carbonate having two cyclic structures including a carbonate group at elevated temperatures less than 200 degrees Centigrade in the presence of a catalyst. The described copolymers evidence excellent mechanical properties, good resorption velocity and do not disintegrate upon degradation into materials of high crystallinity.Type: GrantFiled: June 17, 1994Date of Patent: February 20, 1996Assignee: Rijksuniversiteit te GroningenInventors: Dirk W. Grijpma, Erik Kroeze, Atze J. Nijenhuis, Albertus J. Pennings