Patents Assigned to Natureworks LLC
  • Patent number: 11787932
    Abstract: A polyester blend is made in a reaction of a linear polylactide resin and a thermoplastic epoxy group-containing polymer. The polyester blend is blended with a polyester having a glass transition temperature below 0C to form a polyester blend that is particular useful for making paperboard coatings in a melt extrusion process.
    Type: Grant
    Filed: November 30, 2018
    Date of Patent: October 17, 2023
    Assignee: NatureWorks LLC
    Inventors: Aman Kulshrestha, Eric Meierdierks, Joshua Weed, Nicole Whiteman
  • Patent number: 11739190
    Abstract: Expanded poly(lactide) (PLA) beads are made by pressurizing PLA beads with carbon dioxide at approximately room temperature, heating the beads under pressure to 90 to 160 C to saturate and partially crystallize the beads, and then depressurizing and cooling the beads. The PLA beads contain a blend of PLLA and PDLA in certain ratios. The beads are useful for making expanded bead foam.
    Type: Grant
    Filed: August 21, 2019
    Date of Patent: August 29, 2023
    Assignee: NatureWorks LLC
    Inventors: Nemat Hossieny, Manuel A. W. Natal
  • Patent number: 10807344
    Abstract: Thermal insulation structures include a polymer foam layer adhered to a multi-layer sheet having a non-cellular layer of a heat-resistant thermoplastic and a second non-cellular layer of a polylactide resin. The polylactide resin is a surprisingly good barrier to the diffusion of atmospheric gases into the foam layer and of blowing agents out of the foam layer. Accordingly, the diffusion of atmospheric gases and blowing agents is retarded substantially. This greatly reduces the loss of thermal insulation capacity of the structure due to the replacement of the blowing agent with atmospheric gases. The multi-layer sheet exhibits excellent thermal stability, even when the polylactide in the polylactide layer is highly amorphous.
    Type: Grant
    Filed: April 24, 2017
    Date of Patent: October 20, 2020
    Assignee: NatureWorks LLC
    Inventors: Nemat Hossieny, Osei A. Owusu, Manuel A. W. Natal, Deepak Venkatraman
  • Patent number: 10414714
    Abstract: 2-Acetoxyalkanoic acid esters are made in a reaction of a 3,6-dialkyl-1,4-dioxane-2,5-dione or a poly(?-hydroxyalkanoic acid), an acetate ester and an alcohol or phenol in the presence of a transesterification catalyst. Unlike previous methods for making 2-acetoxyalkanoic acid esters, this process proceeds in high yield and high selectivity to the desired product.
    Type: Grant
    Filed: March 21, 2018
    Date of Patent: September 17, 2019
    Assignee: NatureWorks LLC
    Inventors: Aman Kulshrestha, Joseph David Schroeder
  • Patent number: 10385002
    Abstract: 2-Acetoxyalkanoic acid esters are made in a reaction of a 3,6-dialkyl-1,4-dioxane-2,5-dione or a poly(?-hydroxyalkanoic acid), an acetate ester and an alcohol or phenol in the presence of a transesterification catalyst. Unlike previous methods for making 2-acetoxyalkanoic acid esters, this process proceeds in high yield and high selectivity to the desired product.
    Type: Grant
    Filed: February 23, 2015
    Date of Patent: August 20, 2019
    Assignee: NatureWorks LLC
    Inventors: Aman Kulshrestha, Joseph David Schroeder
  • Patent number: 10294188
    Abstract: 2-Acetoxyalkanoic acid esters are made in a reaction of an ?-hydroxyalkanoic acid ester and an acetate ester in the presence of a transesterification catalyst. Unlike previous methods for making 2-acetoxyalkanoic acid esters, this process proceeds in high yield and high selectivity to the desired product.
    Type: Grant
    Filed: February 23, 2015
    Date of Patent: May 21, 2019
    Assignee: NatureWorks LLC
    Inventors: Aman Kulshrestha, Joseph David Schroeder, Steven Scott Bray
  • Patent number: 10208405
    Abstract: Polylactide fibers are made from a blend of polylactides. One of the polylactides has a ratio of R-lactic and S-lactic units from 8:92 to 92:8. The second polylactide has a ratio of the R-lactic and S-lactic units of ?97:3 or ?3:97. The ratio of the R-lactic units to S-lactic units in the blend is from 7:93 to 25:75 or from 75:25 to 93:7. The polylactide fiber contains at least 5 Joules of polylactide crystallites per gram of polylactide resin in the fiber.
    Type: Grant
    Filed: June 28, 2016
    Date of Patent: February 19, 2019
    Assignee: NatureWorks LLC
    Inventors: Chad Henry Kamann, Robert A. Green
  • Publication number: 20180208537
    Abstract: 2-Acetoxyalkanoic acid esters are made in a reaction of a 3,6-dialkyl-1,4-dioxane-2,5-dione or a poly(?-hydroxyalkanoic acid), an acetate ester and an alcohol or phenol in the presence of a transesterification catalyst. Unlike previous methods for making 2-acetoxyalkanoic acid esters, this process proceeds in high yield and high selectivity to the desired product.
    Type: Application
    Filed: March 21, 2018
    Publication date: July 26, 2018
    Applicant: NatureWorks LLC
    Inventors: Aman Kulshrestha, Joseph David Schroeder
  • Publication number: 20180155747
    Abstract: A process for producing alkyl R-lactate from an initial compound comprising substructure (I) is provided. The process involves producing an intermediate comprising R,R- and S,S-lactide from the initial compound, wherein the initial compound is subjected to stereoisomerisation conditions; and reacting at least a portion of the intermediate with an alkyl alcohol to produce a product comprising alkyl R-lactate, wherein alkyl R-lactate is produced in the presence of an enzyme. Also provided are processes for the production of R-lactic acid, oligomeric R-lactic acid, R,R-lactide, poly-R-lactic acid and stereocomplex lactic acid.
    Type: Application
    Filed: February 1, 2018
    Publication date: June 7, 2018
    Applicant: NatureWorks LLC
    Inventors: Edward Leslie Marshall, Alan Keasey, David Mark Sutton
  • Patent number: 9404032
    Abstract: Polylactide fibers are made from a blend of polylactides. One of the polylactides has a ratio of R-lactic and S-lactic units from 8:92 to 92:8. The second polylactide has a ratio of the R-lactic and S-lactic units of >97:3 or <3:97. The ratio of the R-lactic units to S-lactic units in the blend is from 7:93 to 25:75 or from 75:25 to 93:7. The polylactide fiber contains at least 5 Joules of polylactide crystallites per gram of polylactide resin in the fiber.
    Type: Grant
    Filed: December 14, 2012
    Date of Patent: August 2, 2016
    Assignee: NatureWorks LLC
    Inventors: Chad Henry Kamann, Robert A. Green
  • Patent number: 9284403
    Abstract: This invention provides a method for synthesizing semi-crystalline polylactides (PLA) even from a lactide mixture including meso-LA and rac-LA. According to the invention, when a mixture of racemic lactide and meso-lactide ispolymerized using a catalyst capable of iso-selectively polymerizing L-lactide and D-lactide, an amorphous poly (meso-lactide) block is formed from meso-lactide and a semi-crystalline poly (racemic lactide) block is formed from racemic lactide by separately polymerizing racemic lactide and meso-lactide by taking advantage of a difference in physicochemical properties between racemic lactide and meso-lactide, whereby polylactide which is semi-crystalline as a whole is produced.
    Type: Grant
    Filed: September 11, 2012
    Date of Patent: March 15, 2016
    Assignees: Hitachi Zosen Corporation, Tohoku Electric Power Co., Inc., National University Corporation Nagoya University, NatureWorks LLC
    Inventors: Hisanori Kishida, Takashi Hasegawa, Nobuyoshi Nomura, Makoto Takahashi, Joseph Schroeder, Manuel Natal
  • Patent number: 9035076
    Abstract: Lactic acid equivalents are recovered from a starting lactide stream by catalytically racemizing a portion of the lactide in the stream at a temperature of 180° C. or below. This increases the proportion of two species of lactide (i.e., at least two of S,S-, R,R- or meso-lactide) at the expense of the third species. The racemized mixture so obtained can be separated to recover some or all of one or more of the lactide species from the remaining lactide species, by a process such as melt crystallization or distillation. Impurities in the starting lactide stream usually are retained mostly in the remaining meso-lactide, so a highly purified S,S- and/or R,R-lactide stream can be produced in this manner. Such a purified S,S- and R,R-lactide stream is suitable for polymerization to form a polylactide.
    Type: Grant
    Filed: September 27, 2013
    Date of Patent: May 19, 2015
    Assignee: NatureWorks LLC
    Inventors: Richard Douglas Benson, Joseph D. Schroeder
  • Publication number: 20150087799
    Abstract: This invention provides a method for synthesizing semi-crystalline polylactides (PLA) even from a lactide mixture including meso-LA and rac-LA. According to the invention, when a mixture of racemic lactide and meso-lactide ispolymerized using a catalyst capable of iso-selectively polymerizing L-lactide and D-lactide, an amorphous poly (meso-lactide) block is formed from meso-lactide and a semi-crystalline poly (racemic lactide) block is formed from racemic lactide by separately polymerizing racemic lactide and meso-lactide by taking advantage of a difference in physicochemical properties between racemic lactide and meso-lactide, whereby polylactide which is semi-crystalline as a whole is produced.
    Type: Application
    Filed: September 11, 2012
    Publication date: March 26, 2015
    Applicants: HITACHI ZOSEN CORPORATION, NATUREWORKS LLC, NATIONAL UNIVERSITY CORPORATION NAGOYA UNIVERSITY, TOHOKU ELECTRIC POWER CO., INC.
    Inventors: Hisanori Kishida, Takashi Hasegawa, Nobuyoshi Nomura, Makoto Takahashi, Joseph Schroeder, Manuel Natal
  • Patent number: 8962791
    Abstract: Thermoformed PLA stereocomplex parts are made using a PLA stereocomplex composition having a highest crystallization melting temperature from 200 to 215° C. The stereocomplex composition preferably has less than 5 J/g of lower melting (160 to 190° C.) crystallites. The stereocomplex can be pre-annealed in various ways to reduce thermoforming cycle times. The stereocomplex forms parts with low haze and good thermal resistance, at reasonable cycle times.
    Type: Grant
    Filed: October 24, 2007
    Date of Patent: February 24, 2015
    Assignee: NatureWorks LLC
    Inventor: Richard Douglas Benson
  • Patent number: 8722754
    Abstract: This invention provides an economical process for extruding a PLA resin into a low density foam with a high closed cell content. Excellent quality, low density foam is produced easily and reproducibly. The PLA resin in the foam has a weight average molecular weight of at least 500,000 and an intrinsic viscosity of at least 1.4 deciliters/gram.
    Type: Grant
    Filed: April 24, 2009
    Date of Patent: May 13, 2014
    Assignee: NatureWorks LLC
    Inventors: James Nangeroni, Jed Richard Randall
  • Patent number: 8674056
    Abstract: An S,S- and R,R-lactide stream suitable for polymerization is prepared by producing a low molecular weight poly(lactic acid), depolymerizing the low molecular weight poly(lactic acid) to form a mixture of S,S-, R,R- and meso-lactide, and separating meso-lactide from this mixture to form an S,S- and R,R-lactide stream. Meso-lactide is recycled into the process, and shifts the mole fractions of the lactides in the lactide mixture that is produced.
    Type: Grant
    Filed: March 12, 2010
    Date of Patent: March 18, 2014
    Assignee: NatureWorks LLC
    Inventor: Richard Douglas Benson
  • Publication number: 20140031566
    Abstract: Lactic acid equivalents are recovered from a starting lactide stream by catalytically racemizing a portion of the lactide in the stream at a temperature of 180° C. or below. This increases the proportion of two species of lactide (i.e., at least two of S,S-, R,R- or meso-lactide) at the expense of the third species. The racemized mixture so obtained can be separated to recover some or all of one or more of the lactide species from the remaining lactide species, by a process such as melt crystallization or distillation. Impurities in the starting lactide stream usually are retained mostly in the remaining meso-lactide, so a highly purified S,S- and/or R,R-lactide stream can be produced in this manner. Such a purified S,S- and R,R-lactide stream is suitable for polymerization to form a polylactide.
    Type: Application
    Filed: September 27, 2013
    Publication date: January 30, 2014
    Applicant: NATUREWORKS LLC
    Inventors: Richard Douglas Benson, Joseph D. Schroeder
  • Patent number: 8552209
    Abstract: Lactic acid equivalents are recovered from a starting lactide stream by catalytically racemizing a portion of the lactide in the stream at a temperature of 180° C. or below. This increases the proportion of two species of lactide (i.e., at least two of S,S-, R,R- or meso-lactide) at the expense of the third species. The racemized mixture so obtained can be separated to recover some or all of one or more of the lactide species from the remaining lactide species, by a process such as melt crystallization or distillation. Impurities in the starting lactide stream usually are retained mostly in the remaining meso-lactide, so a highly purified S,S- and/or R,R-lactide stream can be produced in this manner. Such a purified S,S- and R,R-lactide stream is suitable for polymerization to form a polylactide.
    Type: Grant
    Filed: March 12, 2010
    Date of Patent: October 8, 2013
    Assignee: NatureWorks LLC
    Inventors: Richard Douglas Benson, Joseph D. Schroeder
  • Patent number: 8377353
    Abstract: Conjugate fibers are prepared in which at least one segment is a mixture of a high-D PLA resin and a high-L PLA resin. These segments have crystallites having a crystalline melting temperature of at least 200° C. At least one other segment is a high-D PLA resin or a high-L PLA resin. The conjugate fibers may be, for example, bicomponent, multi-component, islands-in-the-sea or sheath-and-core types. Specialty fibers of various types can be made through further downstream processing of these conjugate fibers.
    Type: Grant
    Filed: September 26, 2008
    Date of Patent: February 19, 2013
    Assignee: NatureWorks LLC
    Inventors: Robert A. Green, Chad Henry Kamann, Jeffrey John Kolstad, Christopher M. Ryan
  • Patent number: 8268954
    Abstract: Polyester-carbonate copolymers are prepared by copolymerizing lactide with a 1:4-3:6 dianhydrohexitol in the presence of a carbonate precursor and a polymerization catalyst. The copolymers have an elevated glass transition temperature, relative to polylactide resins.
    Type: Grant
    Filed: August 7, 2008
    Date of Patent: September 18, 2012
    Assignee: NatureWorks LLC
    Inventor: Joseph David Schroeder