Patents Assigned to Synvina C.V.
  • Patent number: 10053442
    Abstract: Dialkyl esters of 2,5-furandicarboxylic acid are prepared from a 2,5-furandicarboxylic acid-containing starting material in a process, which includes: contacting a vaporous stream of an alkanol countercurrently with the at least partially liquid starting material having the 2,5-furandicarboxylic acid, in a reaction zone to conduct an esterification reaction to yield the dialkyl ester of 2,5-furandicarboxylic acid and water; withdrawing a reaction vapor comprising the alkanol and water from the reaction zone; and discharging a liquid phase having at least the dialkyl ester of 2,5-furandicarboxylic acid, from the bottom part of the reaction zone, to obtain the dialkyl ester of 2,5-furandicarboxylic acid.
    Type: Grant
    Filed: November 10, 2015
    Date of Patent: August 21, 2018
    Assignee: Synvina C.V.
    Inventors: Ana Sofia Vagueiro De Sousa Dias, Benjamin McKay, Victor Peter Charles Vreeken, Johannes Maria Franciscus Sijben
  • Patent number: 9951181
    Abstract: Polyamides are made from the polycondensation of monomers including from 15 to 80 mol % of 2,5-furandicarboxylic acid (FDCA), from 20 to 85 mol % of at least one aromatic dicarboxylic acid and from 50 to 100 mol % of at least one aliphatic diamine selected from those including 6 and 7 carbon atoms. A process allowing the synthesis of high molecular weight polyamides made from the above mentioned monomers is also described. Finally, compositions and articles including the same polyamides are also disclosed.
    Type: Grant
    Filed: October 17, 2014
    Date of Patent: April 24, 2018
    Assignee: Synvina C.V.
    Inventors: DeeDee Smith, Joel Flores, René Aberson, Matheus Adrianus Dam, Ate Duursma, Gerardus Johannes M. Gruter
  • Patent number: 9938376
    Abstract: A furan-based polyamide is prepared by the following steps: (1) preparing a furan-based oligomer of formula (1) H2N—R—(NH—CO—F—CO—NH—R)n—NH2 (1) where R is a hydrocarbon moiety and F is a furan (cyclo-C4H2O) moiety and n represents the average degree of oligomerization, and where n is within the range of 1 to 10 by reacting 2,5-furandicarboxylic acid or its derivative with a diamine at a temperature of at most 100° C.; (2) contacting the oligomer of step (1) with a bifunctional linker selected from an acid or a derivative thereof where the acid is furandicarboxylic acid or a non-aromatic dicarboxylic acid; provided that if the hydrocarbon moiety R is aromatic, then the bifunctional linker is an aromatic dicarboxylic acid or a derivative thereof, at a mole ratio of the oligomer to the difunctional linker within the range of 0.8 to 1.5 at polycondensation conditions, and (3) isolating the resulting polyamide.
    Type: Grant
    Filed: October 21, 2014
    Date of Patent: April 10, 2018
    Assignee: Synvina C.V.
    Inventors: Ate Duursma, Rene Aberson, Dee Dee Smith, Joel Flores, Matheus Adrianus Dam, Gerardus Johannes Maria Gruter
  • Patent number: 9908968
    Abstract: A polyester, including ethylene 2,5-furandicarboxylateunits, also includes diethylene glycol residues, the content of which is less than 0.045, in moles per mole of 2,5-furandicarboxylate moieties. The polyester composition can be prepared with a method where a starting mixture is subjected to esterification of 2,5-furandicarboxylic acid or transesterification of an ester thereof with ethylene glycol in the presence of a basic compound and/or an ammonium compound capable of suppressing the formation of diethylene glycol.
    Type: Grant
    Filed: March 11, 2015
    Date of Patent: March 6, 2018
    Assignee: Synvina C.V.
    Inventors: Jeffrey John Kolstad, Bing Wang, Robert Joseph Schiavone, Marion L. Andrews, Jesper Gabriël van Berkel, Edward E. Paschke
  • Patent number: 9902750
    Abstract: A fructoside-containing product is manufactured from a glucose-rich feedstock, in a process where glucose to fructose is isomerized by contacting the glucose-rich feedstock with a basic isomerization catalyst in an alcoholic medium at a temperature of at least 75° C., to yield a fructose-containing product; and where at least part of the fructose-containing product obtained therefrom is reacted with an alcohol in the presence of an acid catalyst to yield a fructoside-containing product.
    Type: Grant
    Filed: June 6, 2014
    Date of Patent: February 27, 2018
    Assignee: Synvina C.V.
    Inventors: Benjamin McKay, Ana Sofia Vagueiro De Sousa Dias, Sarwat Iqbal, Gerardus Johannes Maria Gruter, Robert-Jan Van Putten
  • Patent number: 9896543
    Abstract: Composition including a first component, including furfuryl alcohol and humins and a second component including an acidic polymerization initiator. The composition can be oligomerized to a resin, which has a viscosity in the range of 0.1 to 10,000 Pa·s at 25° C., determined according to ISO3219. The resin, or a blend of furfuryl alcohol and humins as a component A and an acidic polymerization initiator as a component B, separated from each other, may form a kit for an adhesive or impregnation agent.
    Type: Grant
    Filed: December 11, 2014
    Date of Patent: February 20, 2018
    Assignee: Synvina C.V.
    Inventors: Edserd de Jong, Jan Cornelis van der Waal, Jean-Mathieu Benoît Louis Pin, Nathanaël David Cyrille Guigo
  • Patent number: 9896425
    Abstract: An acid composition comprising 2-formyl-furan-5-carboxylic acid and 2,5-furandicarboxylic acid is purified in a process which comprises; contacting the acid composition with an alcohol to obtain an esterified composition; and separating the ester of 2-formyl-furan-5-carboxylic acid from the esterified composition to obtain a purified esterified product; and contacting the purified esterified composition with water for saponification or hydrolysis, to obtain a product composition, comprising 2,5-furandicarboxylic acid and a reduced amount of 2-formyl-furan-5-carboxylic acid.
    Type: Grant
    Filed: August 29, 2014
    Date of Patent: February 20, 2018
    Assignee: SYNVINA C.V.
    Inventors: Jagdeep Singh, Benjamin McKay, Bing Wang, Matheus Adrianus Dam, Gerardus Johannes Maria Gruter, Ana Sofia Vagueiro De Sousa Dias
  • Patent number: 9890242
    Abstract: A polyester, including ethylene 2,5-furandicarboxylate units, has an intrinsic viscosity of at least 0.45 d L/g, and has a relative content of carboxylic acid end groups, expressed as the fraction of the molar amount of carboxylic acid end groups divided by the sum of the molar amounts of hydroxyl end groups and carboxylic acid end groups in the range of 0.10 to 0.70. The polyester can be prepared with a method wherein a starting mixture comprising 2,5-furandicarboxylic acid and ethylene glycol is subjected to esterification and subsequent polycondensation at reduced pressure when the molar ratio of 2,5-furandicarboxylic acid to ethylene glycol in the starting mixture is 1:1.01 to 1:1.15, where water, that is formed during the reaction between 2,5-furandicarboxylic acid and ethylene glycol, and some ethylene glycol are removed in a distillation system, and where ethylene glycol that is removed with water, is separated from water and at least partly recycled.
    Type: Grant
    Filed: March 11, 2015
    Date of Patent: February 13, 2018
    Assignee: Synvina C.V.
    Inventors: Jeffrey John Kolstad, Gerardus Johannes Maria Gruter, Matheus Adrianus Dam, Bing Wang, Robert Joseph Schiavone, Marion L. Andrews, Jesper Gabriël van Berkel, Edward E. Paschke
  • Publication number: 20170320845
    Abstract: Dialkyil esters of 2,5-furandicarboxylic acid are prepared in a process including: contacting an acid starting composition having 2,5-furandicarboxylic acid with an excess of alkanol to form an esterification product having the dialkyil ester of 2,5-furan dicarboxylic acid, water and unreacted alkanol; separating at least part of the unreacted alkanol and water from the esterification product to yield a solid crude product composition having the dialkyil ester of 2,5-furandicarboxylic acid; and subjecting at least part of the solid crude product composition to an evaporation step, where the dialkyil ester of 2,5-furandicarboxylic acid is evaporated and subsequently condensed to yield purified dialkyil ester of 2,5-furandicarboxylic acid.
    Type: Application
    Filed: November 10, 2015
    Publication date: November 9, 2017
    Applicant: Synvina C.V.
    Inventors: Ana Sofia Vagueiro De Sousa Dias, Benjamin McKay, Victor Peter Charles Vreeken, Gerardus Johannes Maria Gruter, Johannes Maria Franciscus Sijben
  • Publication number: 20170297256
    Abstract: An oriented film including poly(ethylene-2,5-furandicarboxylate) is produced in a process by preparing a sheet from a poly(ethylene-2,5-furandicarboxylate) resin by heat processing, which sheet has a thickness of at most 2.5 mm; allowing the sheet to cool; and stretching the cooled sheet in at least one direction with a stretch ratio of at least 4/1 at a temperature in the range of 90 to 130° C., yielding an oriented film. The oriented film has a thickness of 1 to 400 ?m and a tensile strength at break of at least 100 MPa.
    Type: Application
    Filed: August 25, 2015
    Publication date: October 19, 2017
    Applicant: Synvina C.V.
    Inventors: Jeffrey John Kolstad, Jesper Gabriël Van Berkel