Patents Assigned to Furanix Technologies B.V.
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Patent number: 10316140Abstract: A polyester including at least one furandicarboxylate unit, at least one saturated, linear or branched, diol unit including from 2 to 10 carbon atoms, and at least one bicyclic diol unit, the said bicyclic diol being chosen from: isosorbide, isoidide, isomannide, 2,3:4,5-di-O-methylene-galactitol, and 2,4:3,5-di-O-methylene-D-mannitol. The glass transition temperature of the polyester is greater than or equal to 90° C. Processes for preparing this polyester are also described.Type: GrantFiled: March 23, 2015Date of Patent: June 11, 2019Assignees: Furanix Technologies B.V., Roquette FreresInventors: Laszlo Sipos, Gerardus Johannes Maria Gruter, Jeffrey John Kolstad, Gabriel Degand, Nicolas Jacquel, René Saint-Loup, Matheus Adrianus Dam, Joseph D. Schroeder
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Patent number: 10093637Abstract: Psicose is converted into 5-hydroxymethylfurfural or an alkyl ether thereof in a process for the catalyzed conversion of psicose, including the steps of: a. forming a feed including psicose and water or at least one alkanol or a mixture thereof and b. converting the psicose in the feed at a temperature in the range of 50 to 300 degrees Celsius in the presence of a catalyst.Type: GrantFiled: March 5, 2015Date of Patent: October 9, 2018Assignee: Furanix Technologies B.V.Inventors: Robert-Jan van Putten, Jan Cornelis van der Waal, Edserd de Jong
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Patent number: 10030097Abstract: A polyester-containing object, such as an injection stretch blow molded bottle, a biaxially oriented film or a drawn fiber, is made from melt-processing poly(ethylene-2,5-furandicarboxylate). The poly(ethylene-2,5-furandicarboxylate) has a number average molecular weight of at least 25,000, as determined by GPC based on polystyrene standards, and includes an antimony catalyst.Type: GrantFiled: November 16, 2016Date of Patent: July 24, 2018Assignee: Furanix Technologies B.V.Inventors: Laszlo Sipos, Gerardus Johannes Maria Gruter, Jeffrey John Kolstad, Matheus Adrianus Dam
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Patent number: 9840582Abstract: A polyester including poly(ethylene 2,5-furandicarboxylate is prepared by esterification of a starting mixture including 2,5-furandicarboxylic acid and ethylene glycol to form an ester composition, and by subjecting the ester composition thus obtained to polycondensation at reduced pressure in the presence of a polycondensation catalyst to obtain a polycondensate. The mixture is reacted under conditions such that the esterification potential as defined by Esterification Potential (EsPo)=(MR?1)2*PH2O(T), where MR represents the molar ratio of ethylene glycol over 2,5-furandicarboxylic acid, MR being greater than 1; PH2O(T) represents the pure component vapor pressure (in bar) of water at temperature T, which is the final reaction temperature in the esterification mixture before the pressure is reduced to effect the polycondensation, is less than 0.8.Type: GrantFiled: March 11, 2015Date of Patent: December 12, 2017Assignee: Furanix Technologies B.V.Inventors: Jeffrey John Kolstad, Matheus Adrianus Dam, Bing Wang, Robert Joseph Schiavone, Marion L. Andrews, Edward E. Paschke
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Patent number: 9765183Abstract: A process for preparing a polymer having a 2,5-furandicarboxylate moiety within the polymer backbone and having a number average molecular weight of at least 10,000 (as determined by GPC based on polystyrene standards) includes a first step wherein a prepolymer is made having the 2,5-furandicarboxylate moiety within the polymer backbone, followed in a second step by a polycondensation reaction. In the first step a 2,5-furandicarboxylate ester is transesterified with a compound or mixture of compounds containing two or more hydroxyl groups, in the presence of a tin(IV) based transesterification catalyst. In the second step at reduced pressure and under melt conditions the prepolymer prepared in the first step is polycondensed in the presence of a tin (II) based polycondensation catalyst until the polymer is obtained. This polymer may then be subjected to Solid State Polycondensation.Type: GrantFiled: July 7, 2016Date of Patent: September 19, 2017Assignee: Furanix Technologies B.V.Inventor: Laszlo Sipos
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Publication number: 20170129994Abstract: A polyester including at least one furandicarboxylate unit, at least one saturated, linear or branched, diol unit including from 2 to 10 carbon atoms, and at least one bicyclic diol unit, the said bicyclic diol being chosen from: isosorbide, isoidide, isomannide, 2,3:4,5-di-O-methylene-galactitol, and 2,4:3,5-di-O-methylene-D-mannitol. The glass transition temperature of the polyester is greater than or equal to 90° C. Processes for preparing this polyester are also described.Type: ApplicationFiled: March 23, 2015Publication date: May 11, 2017Applicants: Furanix Technologies B.V., Roquette FrèresInventors: Laszlo Sipos, Gerardus Johannes Maria Gruter, Jeffrey John Kolstad, Gabriel Degand, Nicolas Jacquel, René Saint-Loup, Matheus Adrianus Dam, Joseph D. Schroeder
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Patent number: 9643945Abstract: 2,5-Furandicarboxylic acid and methyl acetate are prepared in a continuous process by introducing a 5-methoxymethylfurfural-containing feedstock, an oxygen-containing gas, an oxidation catalyst and an acetic acid-containing solvent into a reactor; allowing 5-methoxymethylfurfural to react with oxygen and acetic acid in the presence of the oxidation catalyst to yield 2,5-furandicarboxylic acid as main product and methyl acetate; withdrawing 2,5-furandicarboxylic acid-containing product from the reactor and recovering 2,5-furandicarboxylic acid product; and withdrawing a vaporous stream containing methyl acetate from the reactor.Type: GrantFiled: April 4, 2014Date of Patent: May 9, 2017Assignee: FURANIX TECHNOLOGIES B.V.Inventors: Etienne Mazoyer, Ana Sofia Vagueiro De Sousa Dias, Benjamin McKay, Hendrikus Jacob Baars, Victor Peter Charles Vreeken, Gerardus Johannes Maria Gruter, David Lee Sikkenga
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Patent number: 9637437Abstract: Benzene derivatives of the formula (I); wherein R1 and R2, are the same or different and independently are selected from the group consisting of hydrogen, alkyl, aralkyl, —CHO, —CH2OR3, —CH(OR4)(OR5) and —COOR6, wherein R3, R4 and R5 are the same or different and are selected from hydrogen, alkyl, aryl, alkaryl, aralkyl, alkylcarbonyl or arylcarbonyl, or wherein R4 and R5 together form an alkylene group and wherein R6 is selected from hydrogen, alkyl and aryl, are prepared in a process, which comprises: reacting a furan derivative of formula (II): wherein R1 and R2 have the meanings above, with ethylene under cycloaddition reaction conditions in the presence of an acid solvent to produce the benzene derivative, wherein the acid solvent is a carboxylic acid and is present in a weight ratio acid solvent to furan derivative from 1:1 to 250:1.Type: GrantFiled: October 22, 2013Date of Patent: May 2, 2017Assignees: FURANIX TECHNOLOGIES B.V., THE COCA-COLA COMPANYInventors: Bing Wang, Gerardus Johannes Maria Gruter, Matheus Adrianus Dam, Robert Michael Kriegel
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Publication number: 20170073462Abstract: A polyester including poly(ethylene 2,5-furandicarboxylate is prepared by esterification of a starting mixture including 2,5-furandicarboxylic acid and ethylene glycol to form an ester composition, and by subjecting the ester composition thus obtained to polycondensation at reduced pressure in the presence of a polycondensation catalyst to obtain a polycondensate. The mixture is reacted under conditions such that the esterification potential as defined by Esterification Potential (EsPo)=(MR?1)2*PH2O(T), where MR represents the molar ratio of ethylene glycol over 2,5-furandicarboxylic acid, MR being greater than 1; PH2O(T) represents the pure component vapor pressure (in bar) of water at temperature T, which is the final reaction temperature in the esterification mixture before the pressure is reduced to effect the polycondensation, is less than 0.8.Type: ApplicationFiled: March 11, 2015Publication date: March 16, 2017Applicant: Furanix Technologies B.V.Inventors: Jeffrey John Kolstad, Matheus Adrianus Dam, Bing Wang, Robert Joseph Schiavone, Marion L. Andrews, Edward E. Paschke
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Publication number: 20170066870Abstract: 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: ApplicationFiled: March 11, 2015Publication date: March 9, 2017Applicant: Furanix Technologies B.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
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Publication number: 20170066875Abstract: A polyester-containing object, such as an injection stretch blow moulded bottle, a biaxially oriented film or a drawn fibre, is made from melt-processing poly(ethylene-2,5-furandicarboxylate). The poly(ethylene-2,5-furandicarboxylate) has a number average molecular weight of at least 25,000, as determined by GPC based on polystyrene standards, and includes an antimony catalyst.Type: ApplicationFiled: November 16, 2016Publication date: March 9, 2017Applicant: Furanix Technologies B.V.Inventors: Laszlo Sipos, Gerardus Johannes Maria Gruter, Jeffrey John Kolstad, Matheus Adrianus Dam
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Patent number: 9567431Abstract: A process for preparing a polymer having a 2,5-furandicarboxylate moiety within the polymer backbone and having a number average molecular weight of at least 10,000 (as determined by GPC based on polystyrene standards) includes a first step where a prepolymer is made having the 2,5-furandicarboxylate moiety within the polymer backbone, followed in a second step by a polycondensation reaction. Polymers so produced may have a 2,5-furandicarboxylate moiety within the polymer backbone, and having a number average molecular weight of at least 20,000 (as determined by GPC based on styrene standards), and an absorbance as a 5 mg/mL solution in a dichloromethane:hexafluoroisopropanol 8:2 at 400 nm of below 0.05.Type: GrantFiled: December 30, 2009Date of Patent: February 14, 2017Assignee: FURANIX TECHNOLOGIES B.V.Inventor: Laszlo Sipos
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Publication number: 20170015781Abstract: The molecular weight of a semi-crystalline starting polyester comprising ethylene 2,5-furandicarboxylate units is enhanced by heating the semi-crystalline starting polyester, having a melting point Tm, at a temperature in the range of (Tm-40° C.) to Tm to obtain a solid stated polyester, where the semi-crystalline starting polyester has an intrinsic viscosity of at least 0.45 dL/g, and an amount of carboxylic acid end groups in the range of 15 to 122 meq/kg.Type: ApplicationFiled: March 11, 2015Publication date: January 19, 2017Applicant: Furanix Technologies B.V.Inventors: Jeffrey John Kolstad, Gerardus Johannes Maria Gruter, Matheus Adrianus Dam, Jesper Gabriël van Berkel, Robert Joseph Schiavone, Marion L. Andrews
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Publication number: 20170015780Abstract: 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: ApplicationFiled: March 11, 2015Publication date: January 19, 2017Applicant: Furanix Technologies B.V.Inventors: Jeffrey John Kolstad, Bing Wang, Robert Joseph Schiavone, Marion L. Andrews, Jesper Gabriël van Berkel, Edward E. Paschke
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Patent number: 9527954Abstract: A process for preparing a polymer having a 2,5-furandicarboxylate moiety within the polymer backbone, and having a number average molecular weight of at least 25,000, includes a transesterification step, a polycondensation step, a drying and/or crystallizing step, and a step where the polymer is subjected to post condensation conditions, and to a polyester-containing bottle or film or fiber-containing woven or non-woven object made from melt-processing poly(ethylene-2,5-furandicarboxylate), where the poly(ethylene-2,5-furandicarboxylate) is obtainable by the process of the invention.Type: GrantFiled: October 24, 2012Date of Patent: December 27, 2016Assignee: Furanix Technologies B.V.Inventors: Laszlo Sipos, Gerardus Johannes Maria Gruter, Jeffrey John Kolstad, Matheus Adrianus Dam
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Publication number: 20160312008Abstract: A process for preparing a polymer having a 2,5-furandicarboxylate moiety within the polymer backbone and having a number average molecular weight of at least 10,000 (as determined by GPC based on polystyrene standards) includes a first step where a prepolymer is made having the 2,5-furandicarboxylate moiety within the polymer backbone, followed in a second step by a polycondensation reaction. In the first step a 2,5-furandicarboxylate ester is transesterified with a compound or mixture of compounds containing two or more hydroxyl groups, in the presence of a tin(IV) based transesterification catalyst. In the second step at reduced pressure and under melt conditions the prepolymer prepared in the first step is polycondensed in the presence of a tin (II) based polycondensation catalyst until the polymer is obtained. This polymer may then be subjected to Solid State Polycondensation.Type: ApplicationFiled: July 7, 2016Publication date: October 27, 2016Applicant: Furanix Technologies B.V.Inventor: Laszlo Sipos
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Patent number: 9434708Abstract: In a process for carrying out a reaction, a liquid reaction mixture is contacted with a catalyst that includes silica and/or a silicate, in which process a silicon compound that is soluble in the liquid reaction mixture is added to the reaction mixture before being contacted with the catalyst. The aqueous reaction mixture suitably contains water, an alcohol or a mixture thereof.Type: GrantFiled: December 27, 2012Date of Patent: September 6, 2016Assignee: FURANIX TECHNOLOGIES B.V.Inventors: Ana Sofia Vagueiro De Sousa Dias, Jan Cornelis Van Der Waal, Etienne Mazoyer
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Publication number: 20160237211Abstract: 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: ApplicationFiled: October 21, 2014Publication date: August 18, 2016Applicant: Furanix Technologies B.V.Inventors: Ate Duursma, Rene Aberson, Dee Dee Smith, Joel Flores, Matheus Adrianus Dam, Gerardus Johannes Maria Gruter
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Publication number: 20160207898Abstract: 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: ApplicationFiled: August 29, 2014Publication date: July 21, 2016Applicant: FURANIX TECHNOLOGIES B.V.Inventors: Jagdeep SINGH, Benjamin MCKAY, Bing WANG, Matheus Adrianus DAM, Gerardus Johannes Maria GRUTER, Ana Sofia Vagueiro DE SOUSA DIAS
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Publication number: 20160138193Abstract: A fiber comprising polyethylene-2,5-furan-dicarboxylate, is prepared by melt spinning in a process wherein a molten composition comprising polyethylene-2,5-furan-dicarboxylate having an intrinsic viscosity of at least 0.55 dl/g, determined in dichloroacetic acid at 25° C., is passed through one or more spinning openings to yield molten threads; wherein the molten threads are cooled to below the melting temperature of the composition to yield spun fibers; and wherein the spun fibers are drawn to a linear density in the range of 0.05 to 2.0 tex per fiber. The invention also proves a fiber comprising polyethylene-2,5-furan-dicarboxylate having a linear density of 0.05 to 2.0 tex, wherein the polyethylene-2,5-furan-dicarboxylate has an intrinsic viscosity of at least 0.45 dl/g, determined in dichloroacetic acid at 25° C.Type: ApplicationFiled: June 20, 2014Publication date: May 19, 2016Applicant: FURANIX TECHNOLOGIES B.V.Inventors: Jeffrey John KOLSTAD, Gerardus Johannes Maria GRUTER