Solid Polymer Derived From Carboxylic Acid Cyclic Ester, E.g., Lactone, Etc. Patents (Class 525/415)
  • Patent number: 11629223
    Abstract: Biodegradable polymers with advantageous physical and chemical properties are described, as well as methods for making such polymers. In one embodiment, a new chemical synthesis route to technologically important biodegradable poly(3-hydroxybutyrate) (P3HB) with high isotacticity and molecular weight required for a practical use is described. The new route can utilize racemic eight-membered cyclic diolide (rac-DL), meso-DL, or a rac-DL and meso-DL mixture, derived from bio-sourced dimethyl succinate, and enantiomeric (R,R)-DL and (S,S)-DL, optically resolved by metal-based catalysts. With a stereoselective racemic molecular catalyst, the ROP of rac-DL under ambient conditions produces rapidly P3HB with essentially perfect isotacticity ([mm]>99%), high crystallinity and melting temperature (Tm=171° C.), as well as high molecular weight and low dispersity (Mn=1.54×105 g/mol, Ð=1.01).
    Type: Grant
    Filed: March 19, 2021
    Date of Patent: April 18, 2023
    Assignee: Colorado State University Research Foundation
    Inventors: Eugene Y. Chen, Xiaoyan Tang
  • Patent number: 10863984
    Abstract: A surgical stapler end effector comprises a staple cartridge, an anvil, and a buttress assembly. The staple cartridge comprises a plurality of staples and a deck. The staple cartridge is operable to drive the staples through the deck. The anvil is movable from an open position toward the staple cartridge to reach a closed position. The anvil includes an underside having staple forming surface configured to receive staples driven through the deck. The buttress assembly comprises a buttress body and an adhesive material. The adhesive material comprises a polymer. The polymer is bioabsorbable. The polymer has an inherent viscosity at or below 3.0 dL/g.
    Type: Grant
    Filed: March 25, 2015
    Date of Patent: December 15, 2020
    Assignee: Ethicon LLC
    Inventors: Frederick E. Shelton, IV, Rao S. Bezwada, Christopher W. Widenhouse
  • Patent number: 10856065
    Abstract: An earpiece including an intra-auricular support, a projection element coupled thereto, and a flexible body disposed thereon and inside an external ear canal of an ear, and a moldable earpiece material moldable about the intra-auricular support to conform to the auricle of an ear and curable to provide a fixed configuration of the earpiece.
    Type: Grant
    Filed: October 23, 2019
    Date of Patent: December 1, 2020
    Assignee: Decibullz LLC
    Inventor: Kyle J Kirkpatrick
  • Patent number: 10786980
    Abstract: A laminate has at least one polylactic acid resin-containing layer (C) with a thickness of 10-500 nm on at least one surface of a fibrous structure (B) containing a water-soluble resin (A). A production method for the laminate is characterized in that water or an aqueous solution is applied to the joining surface of the fibrous structure (B) and the polylactic acid resin-containing layer (C). The laminate exhibits excellent followability, adherence and coatability relative to flexible, curved adherends, exhibits excellent compatibility to organs such as skin and internal organs, and, because the fibrous structure (B) containing a water-soluble resin (A) can easily be removed from the polylactic acid resin-containing layer (C) by the aqueous solution, is adapted for use in materials for external use on the skin, such as wound-dressing materials, adhesion-preventing materials, and skin care products.
    Type: Grant
    Filed: June 18, 2015
    Date of Patent: September 29, 2020
    Assignee: Toray Industries, Inc.
    Inventors: Yuki Sekido, Motonori Hochi, Toru Arakane, Yoshikazu Yakake, Teruhisa Sato
  • Patent number: 10695914
    Abstract: A gripper device (16; 30; 56; 90; 120) which is designed so as to be movable along a movement path, and which serves for grasping and holding a workpiece (70) and for moving the workpiece along the movement path, with at least one first contact section (18; 38; 66) which, to produce an operative pairing with the workpiece that effects the gripping or holding action, can be driven relative to a second contact section (20; 40; 68), which first contact section is assigned actuator means (22; 44; 54; 128), which are designed to exert a drive force in reaction to the application of a magnetic field, and which are composed of a magnetic shape-memory alloy material, wherein the actuator means for magnetic interaction are formed, for the application of a magnetic field, with magnetic field generating means that are static at one position of the movement path (52; 80; 86; 88), and/or with magnetic field generating means that are provided so as to be movable independently of the gripper device.
    Type: Grant
    Filed: July 6, 2015
    Date of Patent: June 30, 2020
    Assignee: ETO Magnetic GmbH
    Inventors: Thomas Schiepp, Markus Laufenberg, Markus Raab, Bernhard Ernst
  • Patent number: 10655012
    Abstract: The present invention provides silicon-based polycarbonates, processes for their preparation and their use in the synthesis of copolymers, in particular segmented copolymers such as polyurethanes for biomedical applications.
    Type: Grant
    Filed: June 8, 2016
    Date of Patent: May 19, 2020
    Assignee: Aortech International plc
    Inventors: Francis P. Maguire, Sriram Venkataramani
  • Patent number: 10577456
    Abstract: Halogenated cyclic diesters, halogenated polymers derived from the cyclic diesters, and methods for making the halogenated cyclic diesters and related halogenated polymers.
    Type: Grant
    Filed: August 16, 2017
    Date of Patent: March 3, 2020
    Inventors: Buddy D. Ratner, Razieh Khalifehzadeh, Esmaeel Naeemi, Chang-Uk Lee, Andrew J. Boydston
  • Patent number: 10406004
    Abstract: A radiation and radiochemically sterilized, multi-component, fiber-reinforced composite, absorbable/disintegratable urinogenital stent, such as an endoureteral stent, with radiomodulated residence time in the biological site of 1 to 10 weeks depending on the high energy radiation dose used for sterilization.
    Type: Grant
    Filed: February 6, 2015
    Date of Patent: September 10, 2019
    Assignee: POLY-MED, INC.
    Inventors: Shalaby W. Shalaby, Kenneth W. Clinkscales, Kenneth David Gray
  • Patent number: 10399956
    Abstract: A method for producing lactide including the steps of: providing a solution of lactic acid in a volatile organic solvent, subjecting the solution to an evaporation step to remove volatile organic solvent and water, resulting in the formation of a composition including lactic acid oligomer, adding catalyst to the composition including lactic acid oligomer, and bringing the mixture to reaction conditions, to form lactide. It has been found that the process results in the efficient production of lactide with a high production rate and a good product quality.
    Type: Grant
    Filed: February 11, 2016
    Date of Patent: September 3, 2019
    Assignee: PURAC BIOCHEM B.V.
    Inventors: Wim Jacob Groot, Jan Van Krieken, Tanja Dekic Zivkovic, Andre Banier De Haan
  • Patent number: 10240007
    Abstract: A method for preparing a shaped polylactide article including stereocomplex polylactide and to a shaped article obtainable by the method. In particular the method comprises melt mixing and solidifying poly-L-lactide (PLLA) and poly-D-lactide (PDLA) homopolymers in a weight ratio whereby one of the homopolymers is in excess, subsequently solid mixing the so obtained blend with additional homopolymer, and shaping the obtained solids mixture.
    Type: Grant
    Filed: December 2, 2015
    Date of Patent: March 26, 2019
    Assignee: PURAC BIOCHEM BV
    Inventors: Siebe Cornelis De Vos, Robert Edgar Haan, Geraldus Gerardus Johannes Schennink
  • Patent number: 10106642
    Abstract: The present invention relates to biodegradable copolyesters with molecular weight Mn from 10 000 to 100 000 measured by GPC, obtainable via reaction of i) from 51 to 84% by weight, based on the copolyester, of a branched polyester middle block produced from aliphatic or aliphatic and aromatic dicarboxylic acids and from aliphatic dihydroxy compounds with molecular weight Mn from 5000 to 25 000 measured by 1H NMR with from 15.9 to 48.9% by weight, based on the copolyester, of a lactide in the presence of a catalyst, and then the resultant polyester triblock with molecular weight Mn measured by 1H NMR from 5800 to 49 500 with ii) from 0.1 to 3% by weight, based on the copolyester, of a diisocyanate. The present invention further relates to a process for the production of, and to the use of, the abovementioned biodegradable copolyesters.
    Type: Grant
    Filed: November 30, 2015
    Date of Patent: October 23, 2018
    Assignee: BASF SE
    Inventors: Kian Molawi, Robert Loos, Andreas Künkel
  • Patent number: 9840593
    Abstract: Phase segregated block-copolymer based on repeating structural elements represented by formula I wherein PHA represents at least one block based on one or more ?-hydroxy acids, PDAS represents a central block based on a dialkylsiloxane, the PDAS block has a weight average molecular weight in the range of from 4000 to 10000, the blocks PHA have a weight average molecular weight in the range of from 2000 to 10 000, the phase segregated block copolymer has a weight average molecular weight of from 40 000 to 120 000.
    Type: Grant
    Filed: April 21, 2016
    Date of Patent: December 12, 2017
    Assignee: ALBERT-LUDWIGS-UNIVERSITÄT FREIBURG
    Inventors: V. Prasad Shastri, Maziar Matloubigharagozloo
  • Patent number: 9814453
    Abstract: The guidance and positioning device may be a system for creating a passage in tissue, positioning fasteners or other implants, and tensioning an elongated fastening member, like a suture, thread, wire, or pin. In some embodiments, the device may allow for the implantation of multiple sutures and fasteners in tissue. A fastener may be positioned at the distal end of a flexible pushrod. The fastener may be connected with the pushrod or may be loosely fitted with the distal end of the pushrod. A suture may be looped through or connected with the fastener such that one, two, or more sections, legs, strands, or portions of the suture extend from the fastener.
    Type: Grant
    Filed: April 26, 2013
    Date of Patent: November 14, 2017
    Assignee: P Tech, LLC
    Inventors: Peter M. Bonutti, Glen A. Phillips
  • Patent number: 9777109
    Abstract: The present invention relates to an improved process for producing polylactide where the goal is to recover a maximum of useful matters in order to recycle without loss and so significantly improving the global yield of the production process of polylactide when starting from lactic acid.
    Type: Grant
    Filed: December 9, 2014
    Date of Patent: October 3, 2017
    Assignee: Futerro S.A.
    Inventors: Christian Penu, Philippe Coszach, Marie-Astrid Feron, Arnaud Delrue
  • Patent number: 9714318
    Abstract: A support material for use in an additive manufacturing system, which compositionally includes a polyglycolic acid polymer, which is at least partially soluble in an aqueous solution, and which is configured for use in the additive manufacturing system for printing a support structure in coordination with printing of a three-dimensional part.
    Type: Grant
    Filed: July 26, 2013
    Date of Patent: July 25, 2017
    Assignee: Stratasys, Inc.
    Inventors: Vittorio L. Jaker, James E. Orrock, Christopher Scott Graley
  • Patent number: 9504768
    Abstract: A biodegradable material has an improved biodegradability, an enhanced shape recovery rate after deformation of the material and an improved flexibility. The biodegradable material is a chemically cross-linked product of: a multivalent compound A having 3 or more functional groups X such as hydroxyl group; a multivalent compound B having 3 or more functional groups Y such as carboxyl group; and a compound C having a structure originated from a hydroxycarboxylic acid whose homopolymer formed by homopolymerization has a glass transition point of ?40° C. or lower.
    Type: Grant
    Filed: March 28, 2013
    Date of Patent: November 29, 2016
    Assignee: Toray Industries, Inc.
    Inventors: Masaki Fujita, Megumi Nakanishi, Kazuhiro Tanahashi
  • Patent number: 9475912
    Abstract: This application discloses a method of photomechanically manipulating optically fixable SMPs that employ glassy, photoresponsive polymeric materials, which are capable of rapid optical-fixing with short exposures (<<5 min) of eye-safe visible light. Key to the optical fixing is the use of polymeric materials composed of covalently attached photochromic units such as azobenzene and the use of light capable of inducing simultaneous trans-cis and cis-trans isomerization of azobenzene or other photochromic moieties capable of similar cycling. Upon exposure to light in this wavelength regime (440-514 nm for the azobenzene unit here), real and lasting reconfigurations are induced capable of fixing both the optically induced strain as well as mechanically induced strain. A linear dependence of bending angle on polarization angle is observed and may be used to control the shape reconfiguration of the SMPs.
    Type: Grant
    Filed: August 24, 2015
    Date of Patent: October 25, 2016
    Assignee: The United States of America, as represented by the Secretary of the Air Force
    Inventors: Timothy J. White, Kyung Min Lee
  • Patent number: 9475939
    Abstract: The present invention relates to a polyurethane polymer composition prepared by reacting a mixture comprising: a} at least one polyethylene glycol, and either b) at least one poly-isocyanate, having a functionality greater than 2 or c) at least one di-isocyanate and at least one polyol or at least one macropolyol having a functionality greater than 2, wherein the polyol or macropolyol is present at an amount of 0.1 to 9 wt % of the mixture. The invention also relates to a process for preparing a polyurethane xerogel in the form of a molded article, said process comprising the steps of: i.) preparing said mixture; ii.) dispensing the reaction mixture formed in step i) into a mold; iii.) allowing the reaction mixture to react and cure; iv.) removing the molded article from the mold; and v.) hydrating the molded article.
    Type: Grant
    Filed: October 24, 2011
    Date of Patent: October 25, 2016
    Assignee: OCUTEC LIMITED
    Inventors: Rashid Abdul, Neil Bonnette Graham
  • Patent number: 9381693
    Abstract: The present invention provides a transparent, dimensionally stable, biaxially oriented PLA film having a haze value of less than 3% and exhibiting strain induced crystallinity having been oriented by stretching the film from a substantially non-crystalline state by more than three times its original areal dimensions. The processes for making such films are also disclosed.
    Type: Grant
    Filed: December 23, 2013
    Date of Patent: July 5, 2016
    Assignee: INNOVIA FILMS LIMITED
    Inventors: Jonathan C. E. Hewitt, Christopher S. Konkel
  • Patent number: 9365672
    Abstract: A polylactic acid triblock copolymer and a preparation method thereof are described. The polylactic acid triblock copolymer comprises an aromatic polyester oligomer block and a polylactic acid block. The polylactic acid triblock copolymer is obtained by reacting an aromatic polyester oligomer with a monomer lactide at a desired temperature. The polylactic acid block copolymer has a regular structure indicated by peak melting temperatures (Tm) corresponding to the aromatic polyester oligomer block and the polylactic acid block, respectively. Examples of the aromatic polyester oligomer block include polyethylene terephthalate, polybutylene terephthalate, and polyethylene 1,4-naphthalate. Examples of the monomer lactide include L-lactide and D-lactide.
    Type: Grant
    Filed: November 29, 2011
    Date of Patent: June 14, 2016
    Assignee: Ningbo Institute of Material Technology and Engineering, Chinese Academy of Sciences
    Inventors: Jian Zhou, Peng Chen, Qun Gu, Jun Li, Wentao Shi, Zongbao Wang, Zhiqiang Jiang, Xuedong Wu
  • Patent number: 9346922
    Abstract: A flame retardant block copolymer is prepared from renewable content. In an exemplary synthetic method, a bio-derived flame retardant block copolymer is prepared by a ring opening polymerization of a biobased cyclic ester and a phosphorus-containing polymer. In some embodiments, the biobased cyclic ester is lactide. In some embodiments, the phosphorus-containing polymer is a hydroxyl-telechelic flame retardant biopolymer prepared by a polycondensation reaction of a biobased diol (e.g., isosorbide) and a phosphorus-containing monomer (e.g., phenylphosphonic dichloride). In other embodiments, the phosphorus-containing polymer is synthesized from a dioxaphospholane monomer.
    Type: Grant
    Filed: November 26, 2013
    Date of Patent: May 24, 2016
    Assignee: International Business Machines Corporation
    Inventors: Dylan J. Boday, Joseph Kuczynski, Timothy C. Mauldin
  • Patent number: 9228050
    Abstract: Polylactic acid-backbone graft and bottlebrush copolymers are synthesized by polymerizing a lactide-functionalized macromonomer using ring opening polymerization (ROP). In some embodiments of the present invention, the macromonomer is a lactide-functionalized polymer that may be synthesized by, for example, polymerizing a monomer capable of undergoing radical polymerization (e.g., styrenic, vinylic, acrylic, etc.) using a brominated lactide initiator via atom transfer radical polymerization (ATRP). The brominated lactide initiator may be 3-bromo-3,6-dimethyl-1,4-dioxane-2,5-dione prepared by, for example, reacting lactide with N-bromosuccinimide in the presence of benzoyl peroxide.
    Type: Grant
    Filed: October 27, 2014
    Date of Patent: January 5, 2016
    Assignee: International Business Machines Corporation
    Inventors: Dylan J. Boday, Timothy C. Mauldin
  • Patent number: 9228044
    Abstract: Polylactic acid-backbone graft and bottlebrush copolymers are synthesized by polymerizing a lactide-functionalized macromonomer using ring opening polymerization (ROP). In some embodiments of the present invention, the macromonomer is a lactide-functionalized polymer that may be synthesized by, for example, polymerizing a monomer capable of undergoing radical polymerization (e.g., styrenic, vinylic, acrylic, etc.) using a brominated lactide initiator via atom transfer radical polymerization (ATRP). The brominated lactide initiator may be 3-bromo-3,6-dimethyl-1,4-dioxane-2,5-dione prepared by, for example, reacting lactide with N-bromosuccinimide in the presence of benzoyl peroxide.
    Type: Grant
    Filed: April 2, 2014
    Date of Patent: January 5, 2016
    Assignee: International Business Machines Corporation
    Inventors: Dylan J. Boday, Timothy C. Mauldin
  • Patent number: 9155638
    Abstract: Disclosed are self-expanding medical implants for placement within a lumen of a patient. The implants comprise a woven or non-woven structure having a substantially tubular configuration, and are designed to be low-profile such that they are deliverable with a small diameter catheter. The implants have a high recoverability and desired mechanical properties.
    Type: Grant
    Filed: May 10, 2013
    Date of Patent: October 13, 2015
    Assignee: 480 BIOMEDICAL, INC.
    Inventors: Maria Palasis, Changcheng You, Danny Concagh, Lee Core, Kicherl Ho, Upma Sharma, Gregory T. Zugates
  • Patent number: 9125944
    Abstract: Provided are a BAB-type tri-block copolymer including a polylactic acid (A) that is a hydrophobic block and polyethylene glycol (B) that is a hydrophilic block, a method of preparing the BAB-type tri-block copolymer including synthesizing a polylactic acid (A)-polyethylene glycol (B) di-block copolymer by a ring opening polymerization of a lactic acid monomer using a hydroxyl group of polyethylene glycol (B) as a polymerization initiator; and synthesizing a BAB-type tri-block copolymer by reacting the AB-type di-block copolymer with polyethylene glycol (B) including at least one carboxyl group at one or more terminals thereof in the presence of a coupling agent and a catalyst, and a drug delivery system using the BAB-type tri-block copolymer.
    Type: Grant
    Filed: October 31, 2011
    Date of Patent: September 8, 2015
    Assignee: CHUNG-ANG UNIVERSITY INDUSTRY-ACADEMY COOPERATION FOUNDATION
    Inventors: Kyung Taek Oh, Jeong Min Yun
  • Patent number: 9023953
    Abstract: A method of producing a poly(lactic acid) resin includes carrying out direct polycondensation using lactic acid as a main raw material to prepare a crystallized prepolymer having a weight average molecular weight of 5,000 to 25,000, an enthalpy of fusion ?Hm of 50 to 65 J/g and an acid value A mol/ton satisfying (1) below: 450/(Mw/10,000?0.14)<A<950/(Mw/10,000?0.14)??(1) (wherein Mw represents weight average molecular weight of the crystallized prepolymer); and subjecting the crystallized prepolymer to solid-phase polymerization.
    Type: Grant
    Filed: June 27, 2011
    Date of Patent: May 5, 2015
    Assignee: Toray Industries, Inc.
    Inventors: Tatsuya Nagano, Tsuyoshi Tanaka, Hiroyuki Ome
  • Patent number: 9006254
    Abstract: This invention relates to compositions, and related compounds and methods, of conjugates of immunomodulatory agents and polymers or unit(s) thereof. The conjugates may be contained within synthetic nanocarriers, and the immunomodulatory agents may be released from the synthetic nanocarriers in a pH sensitive manner.
    Type: Grant
    Filed: December 23, 2013
    Date of Patent: April 14, 2015
    Assignee: Selecta Biosciences, Inc.
    Inventors: Charles Zepp, Grayson B. Lipford, Yun Gao, Lloyd Johnston, Fen-ni Fu, Mark J. Keegan, Sam Baldwin
  • Patent number: 9000101
    Abstract: The disclosure describes a neat, one-pot scheme for reacting a hydroxyl propagating end of a polymer with a cyclic acid anhydride to form a free acid terminus.
    Type: Grant
    Filed: July 10, 2013
    Date of Patent: April 7, 2015
    Assignee: Xerox Corporation
    Inventors: Andrew J. Myles, Jordan H. Wosnick, Karen A. Moffat, Valerie M. Farrugia
  • Publication number: 20150093444
    Abstract: Provided are a polycaprolactone-polyphosphate block copolymer, a liquid composite formed by the block copolymer, a nucleic acid preparation, preparation methods for the copolymer and the liquid composite, and the use of the copolymer and the liquid composite in a nucleic acid medicine delivery system. The block copolymer prepared using the present invention has good biocompatibility, low cytotoxicity, and good biodegradability. The micelles provided in the present invention self-assemble into nano-particles in an aqueous solution, and have good stability, biocompatibility, and biodegradability, and low cytotoxicity. The preparation method is simple, has high repeatability, as a vector can protect small nucleic acids such as siRNA from biodegradation, can combine with the scale effect of nano-particles, and can be used for treating different diseases. Additionally, bonding targeting groups enable specificity recognition of different cancer cells.
    Type: Application
    Filed: October 23, 2012
    Publication date: April 2, 2015
    Applicant: SUZHOU RIBO LIFE SCIENCE CO., LTD.
    Inventors: Hongyan Zhang, Jun Wang
  • Patent number: 8993687
    Abstract: There is provided a method for production of a high-purity biodegradable polyoxyethylene derivative on an industrial scale using a polyoxyethylene compound containing polylactic acid at the terminal thereof. A biodegradable polyoxyethylene compound represented by formula (1) and a compound represented by formula (I) are caused to react with each other at 60° C. to 120° C. using toluene as a solvent in the presence of sodium acetate to obtain a biodegradable polyoxyethylene derivative represented by formula (2).
    Type: Grant
    Filed: March 12, 2014
    Date of Patent: March 31, 2015
    Assignee: NOF Corporation
    Inventors: Kosuke Nishiguchi, Tsuyoshi Takehana, Yuji Yamamoto
  • Publication number: 20150079514
    Abstract: Disclosed herein is a method of making a modified pigment, comprising: reacting, under Mitsunobu conditions: (a) a first reactant comprising a protonated nucleophile having a pKa<15, and (b) a second reactant comprising a hydroxyl-containing organic group, wherein a pigment is attached to either the first or second reactant. The method further comprises forming the modified pigment having attached an organic species comprising the nucleophile bonded to the organic group, with the net elimination of a proton and a hydroxyl. Also disclosed herein are modified pigments, which can have applications in chemical toners, inkjet ink and electrophoretic ink compositions, black matrix materials, color filters, and coatings.
    Type: Application
    Filed: November 20, 2014
    Publication date: March 19, 2015
    Inventors: Qingling Zhang, Lynne K. LaRochelle Richard
  • Patent number: 8975344
    Abstract: The instant disclosure describes polyester synthesis processes, including processes for the ring-opening polymerization (ROP) of cyclic organic monomer components and components comprising a functional group using an organocatalyst system to effect ROP-based block copolymer preparation.
    Type: Grant
    Filed: July 10, 2013
    Date of Patent: March 10, 2015
    Assignee: Xerox Corporation
    Inventors: Andrew J Myles, Karen A Moffat, Jordan H Wosnick, Valerie M Farrugia
  • Patent number: 8969485
    Abstract: The present disclosure relates to coated biodegradable materials having a reduced amount of residual catalysts and methods thereof.
    Type: Grant
    Filed: July 3, 2013
    Date of Patent: March 3, 2015
    Assignee: Covidien LP
    Inventors: Nadya D. Belcheva, Norman Aminuddin
  • Publication number: 20150018494
    Abstract: The disclosure describes a neat, one-pot scheme for reacting a hydroxyl propagating end of a polymer with a cyclic acid anhydride to form a free acid terminus.
    Type: Application
    Filed: July 10, 2013
    Publication date: January 15, 2015
    Inventors: Andrew J. Myles, Jordan H. Wosnick, Karen A. Moffat, Valerie M. Farrugia
  • Patent number: 8927682
    Abstract: Poly(glycolide) polymers are disclosed. The polymers generally include a polymerized alkynyl-substituted glycolide having a polymer backbone with one or more alkynyl groups appended thereto. The alkynyl groups provide reactive sites for further functionalization of the polymer, for example by reaction with azide derivatives (e.g., azide-substituted organic compounds). Alkynyl and azide groups react via the “click” chemistry mechanism to form functional groups covalently bonded to the polymer via a triazole link. The polymers are biodegradable and can be used to deliver drugs or other therapeutic substances (e.g., large biomolecules such as single strand RNA) at targeted locations in a patient's body and/or at controlled release rates.
    Type: Grant
    Filed: August 25, 2008
    Date of Patent: January 6, 2015
    Assignee: Board of Trustees of Michigan State University
    Inventors: Gregory L. Baker, Milton R. Smith, III, Xuwei Jiang, Erin B. Vogel
  • Publication number: 20140357806
    Abstract: The invention relates to materials comprising polymer network containing siloxanes or organic-based core structures, preferably the materials have thermal-responsive properties. In some embodiments, the invention relates to an organic core functionalized with polymers. In another embodiment, organic core-polymer conjugates comprise polylactone segments. The organic core-polymer conjugates may be crosslinked together to form a material, and these materials may be functionalized with bioactive compounds so that the materials have desirable biocompatibility or bioactivity when used in medical devices.
    Type: Application
    Filed: October 21, 2013
    Publication date: December 4, 2014
    Applicant: University of Massachusetts Medical School
    Inventors: Jie Song, Jianwen Xu
  • Patent number: 8901275
    Abstract: A method for producing a crystallized polyester comprises the crystallization step of applying a shear and/or a pressure to a polyester selected from an aliphatic polyester and a polyalkylene terephthalate at a temperature of (Tm?70° C.) to (Tm+20° C.), where Tm is a melting point of the polyester, thereby converting the polyester into a state having a crystallinity of 10% or more and fluidity.
    Type: Grant
    Filed: June 17, 2010
    Date of Patent: December 2, 2014
    Assignee: Toray Industries, Inc.
    Inventors: Mitsushige Hamaguchi, Takuma Naotsuka, Yoshitake Takahashi, Toru Takahashi, Hiroyuki Ome
  • Patent number: 8889823
    Abstract: Methods of making a biodegradable polymeric stent made from poly(L-lactide) and a low concentration of L-lactide monomer is disclosed. The concentration of L-lactide is adjusted to provide a degradation behavior that is suitable for different treatment applications including coronary, peripheral, and nasal. Methods include making a poly(L-lactide) material for a stent with uniformly distributed L-lactide monomer through control of polymerization conditions during PLLA synthesis, control of post-processing conditions, or both.
    Type: Grant
    Filed: March 31, 2010
    Date of Patent: November 18, 2014
    Assignee: Abbott Cardiovascular Systems Inc.
    Inventors: Yunbing Wang, Xiao Ma
  • Patent number: 8877223
    Abstract: The present application discloses biodegradable polymers, to porous and other materials comprising such polymers, and to various medical uses of such materials, including use as a scaffold for supporting cell adhesion or the in-growth for regeneration of tissue. The polymer is of the formula A-O—(CHR1CHR2O)n—B wherein A is a poly(lactide-co-glycolide) residue, the molar ratio of (i) lactide units [—CH(CH3)—COO—] and (ii) glycolide units [—CH2—COO—] in the poly(lactide-co-glycolide) residue being in the range of 80:20 to 10:90, B is either a poly(lactide-co-glycolide) residue or hydrogen, C1-6-alkyl or hydroxy protecting groups, one of R1 and R2 is hydrogen or methyl, and the other is hydrogen, n is 10-1000, the molar ratio of (iii) polyalkylene glycol units [—(CHR1CHR2O)—] to the combined amount of (i) lactide units and (ii) glycolide units in the poly(lactide-co-glycolide) residue(s) is at the most 14:86, and the molecular weight of the copolymer is at least 20,000 g/mol.
    Type: Grant
    Filed: March 7, 2007
    Date of Patent: November 4, 2014
    Assignee: Coloplast A/S
    Inventors: Jakob Vange, Khadija Schwach-Abdellaoui, Hanne Everland, Peter Sylvest Nielsen, Brian Nielsen, Lene Karin Jespersen, Lene Feldskov Nielsen
  • Patent number: 8871242
    Abstract: A blood anticoagulant material is provided which has high expandability, reduced influence on living bodies, and can efficiently prevent blood coagulation. A multiblock copolymer having at least a structural unit represented by Formula (1), a structural unit represented by Formula (2), and a structural unit represented by Formula (3) is used: wherein, R1, R2, and R3 in Formulas (1) to (3) each independently represent a divalent organic group, and m and n each independently represent an integer of 2 to 5000.
    Type: Grant
    Filed: November 16, 2007
    Date of Patent: October 28, 2014
    Assignee: National Cerebral and Cardiovascular Center
    Inventors: Tetsuji Yamaoka, Satoshi Kato, Atsushi Kasai, Sachiro Kakinoki
  • Patent number: 8871876
    Abstract: Ethylene-based interpolymers, e.g., ethylene-acrylic acid copolymers, are made by a process comprising the steps of: A. Injecting a first feed comprising a chain transfer agent system (CTA system) and ethylene into a first autoclave reactor zone to produce a first zone reaction product, the CTA system of the first reactor zone having a transfer activity Z1; and B. (1) Transferring at least part of the first zone reaction product to a second reactor zone selected from a second autoclave reactor zone or a tubular reactor zone, and (2) at least one of transferring or freshly injecting a feed comprising a CTA system into the second reactor zone to produce a second zone reaction product, the CTA system of the second reactor zone having a transfer activity of Z2; and with the proviso that the ratio of Z1:Z2 is greater than 1. The comonomer comprises at least one carboxylic acid group or an anhydride group.
    Type: Grant
    Filed: September 21, 2011
    Date of Patent: October 28, 2014
    Assignee: Dow Global Technologies LLC
    Inventors: Otto J. Berbee, Roger G. Gagnon, Mark Jasek, Laura Nunez, Bryan Gutermuth
  • Patent number: 8846071
    Abstract: A stent having a stent body made from a crosslinked bioabsorbable polymer is disclosed. A method of making the stent including exposing a tube formed from a bioabsorbable polymer to radiation to crosslink the bioabsorbable polymer and forming a stent body from the exposed tube is disclosed. The tube can include a crosslinking agent which induces crosslinking upon radiation exposure. Additionally or alternatively, the bioabsorbable polymer can be a copolymer that crosslinks upon exposure to radiation in the absence of a crosslinking agent.
    Type: Grant
    Filed: February 17, 2012
    Date of Patent: September 30, 2014
    Assignee: Abbott Cardiovascular Systems Inc.
    Inventor: Lothar W. Kleiner
  • Patent number: 8834763
    Abstract: The present disclosure relates to a method of forming fibers. First and second precursors, each possessing a core and at least one functional group known to have click reactivity, are mixed in a hopper. The mixed precursors are then extruded through an extrusion die to crosslink and produce a filament. Polymerization of the first and second precursors is catalyzed by transition metal ions.
    Type: Grant
    Filed: February 22, 2010
    Date of Patent: September 16, 2014
    Assignees: Covidien LP, Sofradim Production
    Inventors: Ahmad Robert Hadba, Sebastien Ladet
  • Patent number: 8835571
    Abstract: A fatty acid derivative-polymer conjugate including a conjugate comprising a fatty acid derivative and an alkyl substituted polylactide compound is provided. A pharmaceutical composition comprising the conjugate is also provided.
    Type: Grant
    Filed: April 19, 2013
    Date of Patent: September 16, 2014
    Assignee: Sucampo AG
    Inventors: Ryuji Ueno, Peter Lichtlen, Robert Gurny, Michael Möller
  • Patent number: 8829121
    Abstract: The invention provides a piezoelectric polymer material comprising a helical chiral polymer having a weight average molecular weight of from 50,000 to 1,000,000 and optical activity, the piezoelectric polymer material having: crystallinity as obtained by a DSC method of from 20% to 80%; a transmission haze with respect to visible light of 50% or less; and a product of the crystallinity and a standardized molecular orientation MORc, which is measured with a microwave transmission-type molecular orientation meter at a reference thickness of 50 ?m, of from 40 to 700.
    Type: Grant
    Filed: February 9, 2012
    Date of Patent: September 9, 2014
    Assignees: Mitsui Chemicals, Inc., A School Corporation Kansai University
    Inventors: Mitsunobu Yoshida, Shunsuke Fujii, Hitoshi Onishi, Yoshiro Tajitsu, Taizo Nishimoto, Kazuhiro Tanimoto, Kenichi Goto
  • Patent number: 8816018
    Abstract: A resin composition which comprises a polyester and is free from a smell produced from a free isocyanate compound. The resin composition comprises a polyester (component A) whose end is modified and a compound including a cyclic structure having one carbodiimide group whose first nitrogen and second nitrogen are bonded together by a bond group (component B).
    Type: Grant
    Filed: December 15, 2009
    Date of Patent: August 26, 2014
    Assignee: Teijin Limited
    Inventors: Shinichiro Shoji, Hirotaka Suzuki
  • Patent number: 8802738
    Abstract: The invention relates to polymers, such as aliphatic polyesters, with grafted zwitterions. More particularly, the invention relates to polyester-graft-phosphorylcholine polymers prepared by ring-opening polymerization and click chemistry, compositions and products comprising same, and related methods and uses, for example, in drug delivery.
    Type: Grant
    Filed: December 11, 2009
    Date of Patent: August 12, 2014
    Assignee: University of Massachusetts
    Inventor: Todd Emrick
  • Publication number: 20140219923
    Abstract: A special class of drug-depot forming triblock copolymers which are very suitable for the loading, containment and releasing of sensitive drugs such as proteins from biodegradable, injectable drug depots. How to visualize these depots for various imaging related purposes is described. A composition comprising a tri-block copolymer according to formula 1 B-A-B (1), wherein A stands for a linear poly-(ethylene glycol) block and wherein B stands for wherein B stands for a poly(lactide-co-?-caprolactone) block, wherein the hydroxyl end-groups of the tri-block copolymer are at least partially acylated with an optionally substituted acyl having 2 to 12 C-atoms, C-atoms of the substituents included; an active ingredient, preferably a pharmaceutically active ingredient and a solvent, wherein the block ratio of the tri-block copolymer, which ratio is defined as the ratio between the sum of the average molecular weight of the B-blocks and the sum of the average molecular weight of the A-block ranges from 1.4 to 3.5.
    Type: Application
    Filed: April 2, 2012
    Publication date: August 7, 2014
    Applicant: INGELL TECHNOLOGIES HOLDING B.V.
    Inventors: Peter Bruin, Audrey Petit, Mike De Leeuw, Martin Piest, Ronald Meijboom
  • Patent number: 8796396
    Abstract: A polylactic acid has a terminal-modified structure represented by the following formula (1): wherein in the formula (1), R represents a residue of an organic phosphorus compound containing an epoxy group, and n represents an integer from 100 to 5000.
    Type: Grant
    Filed: February 27, 2013
    Date of Patent: August 5, 2014
    Assignee: Fuji Xerox Co., Ltd.
    Inventor: Masaya Ikuno
  • Patent number: 8791228
    Abstract: Process for bulk polymerization of lactide at a temperature between 160° C. and 195° C. in the presence of a zinc-based catalyst.
    Type: Grant
    Filed: December 3, 2010
    Date of Patent: July 29, 2014
    Assignee: Futerro S.A.
    Inventor: Sabine Sirol