Patents Assigned to Natureworks LLC
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Patent number: 11787932Abstract: 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: GrantFiled: November 30, 2018Date of Patent: October 17, 2023Assignee: NatureWorks LLCInventors: Aman Kulshrestha, Eric Meierdierks, Joshua Weed, Nicole Whiteman
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Patent number: 11739190Abstract: 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: GrantFiled: August 21, 2019Date of Patent: August 29, 2023Assignee: NatureWorks LLCInventors: Nemat Hossieny, Manuel A. W. Natal
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Patent number: 10807344Abstract: 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: GrantFiled: April 24, 2017Date of Patent: October 20, 2020Assignee: NatureWorks LLCInventors: Nemat Hossieny, Osei A. Owusu, Manuel A. W. Natal, Deepak Venkatraman
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Patent number: 10414714Abstract: 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: GrantFiled: March 21, 2018Date of Patent: September 17, 2019Assignee: NatureWorks LLCInventors: Aman Kulshrestha, Joseph David Schroeder
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Patent number: 10385002Abstract: 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: GrantFiled: February 23, 2015Date of Patent: August 20, 2019Assignee: NatureWorks LLCInventors: Aman Kulshrestha, Joseph David Schroeder
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Patent number: 10294188Abstract: 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: GrantFiled: February 23, 2015Date of Patent: May 21, 2019Assignee: NatureWorks LLCInventors: Aman Kulshrestha, Joseph David Schroeder, Steven Scott Bray
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Patent number: 10208405Abstract: 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: GrantFiled: June 28, 2016Date of Patent: February 19, 2019Assignee: NatureWorks LLCInventors: Chad Henry Kamann, Robert A. Green
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Publication number: 20180208537Abstract: 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: ApplicationFiled: March 21, 2018Publication date: July 26, 2018Applicant: NatureWorks LLCInventors: Aman Kulshrestha, Joseph David Schroeder
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Publication number: 20180155747Abstract: 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: ApplicationFiled: February 1, 2018Publication date: June 7, 2018Applicant: NatureWorks LLCInventors: Edward Leslie Marshall, Alan Keasey, David Mark Sutton
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Patent number: 9404032Abstract: 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: GrantFiled: December 14, 2012Date of Patent: August 2, 2016Assignee: NatureWorks LLCInventors: Chad Henry Kamann, Robert A. Green
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Patent number: 9284403Abstract: 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: GrantFiled: September 11, 2012Date of Patent: March 15, 2016Assignees: Hitachi Zosen Corporation, Tohoku Electric Power Co., Inc., National University Corporation Nagoya University, NatureWorks LLCInventors: Hisanori Kishida, Takashi Hasegawa, Nobuyoshi Nomura, Makoto Takahashi, Joseph Schroeder, Manuel Natal
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Patent number: 9035076Abstract: 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: GrantFiled: September 27, 2013Date of Patent: May 19, 2015Assignee: NatureWorks LLCInventors: Richard Douglas Benson, Joseph D. Schroeder
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Publication number: 20150087799Abstract: 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: ApplicationFiled: September 11, 2012Publication date: March 26, 2015Applicants: 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
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Patent number: 8962791Abstract: 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: GrantFiled: October 24, 2007Date of Patent: February 24, 2015Assignee: NatureWorks LLCInventor: Richard Douglas Benson
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Patent number: 8722754Abstract: 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: GrantFiled: April 24, 2009Date of Patent: May 13, 2014Assignee: NatureWorks LLCInventors: James Nangeroni, Jed Richard Randall
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Patent number: 8674056Abstract: 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: GrantFiled: March 12, 2010Date of Patent: March 18, 2014Assignee: NatureWorks LLCInventor: Richard Douglas Benson
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Publication number: 20140031566Abstract: 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: ApplicationFiled: September 27, 2013Publication date: January 30, 2014Applicant: NATUREWORKS LLCInventors: Richard Douglas Benson, Joseph D. Schroeder
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Patent number: 8552209Abstract: 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: GrantFiled: March 12, 2010Date of Patent: October 8, 2013Assignee: NatureWorks LLCInventors: Richard Douglas Benson, Joseph D. Schroeder
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Patent number: 8377353Abstract: 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: GrantFiled: September 26, 2008Date of Patent: February 19, 2013Assignee: NatureWorks LLCInventors: Robert A. Green, Chad Henry Kamann, Jeffrey John Kolstad, Christopher M. Ryan
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Patent number: 8268954Abstract: 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: GrantFiled: August 7, 2008Date of Patent: September 18, 2012Assignee: NatureWorks LLCInventor: Joseph David Schroeder