公开(公告)号：US09938376B2

公开(公告)日：2018-04-10

申请号：US15029296

申请日：2014-10-21

Applicant: Furanix Technologies B.V.

Inventor： Ate Duursma ,  Rene Aberson ,  Dee Dee Smith ,  Joel Flores ,  Matheus Adrianus Dam ,  Gerardus Johannes Maria Gruter

IPC: C08L77/00 ,  C08G69/26 ,  C08G69/28 ,  C08L77/06 ,  C08J5/18 ,  C08K11/00 ,  C09D177/06

CPC classification number: C08G69/26 ,  C08G69/28 ,  C08J5/18 ,  C08J2377/06 ,  C08K11/00 ,  C08L77/06 ,  C09D177/06

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.

公开(公告)号：US09908968B2

公开(公告)日：2018-03-06

申请号：US15123724

申请日：2015-03-11

Applicant: Furanix Technologies B.V.

Inventor： Jeffrey John Kolstad ,  Bing Wang ,  Robert Joseph Schiavone ,  Marion L. Andrews ,  Jesper Gabriël van Berkel ,  Edward E. Paschke

IPC: C08G63/16 ,  C08G63/181 ,  C08G63/80 ,  C08G63/86

CPC classification number: C08G63/16 ,  C08G63/181 ,  C08G63/80 ,  C08G63/866

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.

公开(公告)号：US09840582B2

公开(公告)日：2017-12-12

申请号：US15122960

申请日：2015-03-11

Applicant: Furanix Technologies B.V.

Inventor： Jeffrey John Kolstad ,  Matheus Adrianus Dam ,  Bing Wang ,  Robert Joseph Schiavone ,  Marion L. Andrews ,  Edward E. Paschke

IPC: C08G63/02 ,  C08G63/80 ,  C08G63/181 ,  C08G63/78 ,  C08G63/16 ,  C08G63/86

CPC classification number: C08G63/80 ,  C08G63/16 ,  C08G63/181 ,  C08G63/78 ,  C08G63/866

Abstract: 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.

公开(公告)号：US20170129994A1

公开(公告)日：2017-05-11

申请号：US15127596

申请日：2015-03-23

Applicant: Furanix Technologies B.V. ,  Roquette Frères

Inventor： Laszlo Sipos ,  Gerardus Johannes Maria Gruter ,  Jeffrey John Kolstad ,  Gabriel Degand ,  Nicolas Jacquel ,  René Saint-Loup ,  Matheus Adrianus Dam ,  Joseph D. Schroeder

IPC: C08G63/672 ,  C08G63/78

CPC classification number: C08G63/672 ,  C08G63/78

Abstract: 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.

公开(公告)号：US09637437B2

公开(公告)日：2017-05-02

申请号：US14435470

申请日：2013-10-22

Applicant: Furanix Technologies B.V.

Inventor： Bing Wang ,  Gerardus Johannes Maria Gruter ,  Matheus Adrianus Dam ,  Robert Michael Kriegel

IPC: C07C51/25 ,  C07C51/50 ,  C07C2/86 ,  C07C51/265 ,  C07C51/353

CPC classification number: C07C51/25 ,  C07C2/865 ,  C07C51/265 ,  C07C51/353 ,  C07C51/50 ,  C07C2521/08 ,  C07C2521/18 ,  C07C2523/44 ,  C07C2523/745 ,  C07C2523/89 ,  Y02P20/582 ,  C07C15/08 ,  C07C15/06 ,  C07C63/26

Abstract: 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.

公开(公告)号：US20170066875A1

公开(公告)日：2017-03-09

申请号：US15353051

申请日：2016-11-16

Applicant: Furanix Technologies B.V.

Inventor： Laszlo Sipos ,  Gerardus Johannes Maria Gruter ,  Jeffrey John Kolstad ,  Matheus Adrianus Dam

IPC: C08G63/672 ,  B29C49/06 ,  B29C49/00 ,  C08G63/86 ,  C08G63/80

CPC classification number: C08G63/672 ,  B29C49/0005 ,  B29C49/06 ,  B29K2023/06 ,  B29L2031/7158 ,  C08G63/181 ,  C08G63/80 ,  C08G63/866

Abstract: 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.

Abstract translation: 通过熔融加工聚（乙烯-2,5-呋喃二羧酸酯）制备含聚酯的物体，例如注射拉伸吹塑成型瓶，双轴取向膜或拉伸纤维。 通过基于聚苯乙烯标准的GPC测定，聚（乙烯-2,5-呋喃二羧酸酯）的数均分子量至少为25,000，并且包括锑催化剂。

公开(公告)号：US20170066870A1

公开(公告)日：2017-03-09

申请号：US15122694

申请日：2015-03-11

Applicant: Furanix Technologies B.V.

Inventor： 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

IPC: C08G63/181 ,  C08G63/80 ,  C08G63/86

CPC classification number: C08G63/181 ,  C08G63/78 ,  C08G63/80 ,  C08G63/866

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.

Abstract translation: 包括2,5-呋喃二甲酸乙二酯单元的聚酯具有至少0.45d L / g的特性粘度，并且具有羧酸端基的相对含量，以羧酸端基的摩尔量的分数表示 通过羟基端基和羧酸端基的摩尔量的总和在0.10至0.70的范围内。 聚酯可以通过以下方法制备：其中包含2,5-呋喃二甲酸和乙二醇的起始混合物在起始混合物中进行酯化反应并随后在减压下进行缩聚，当起始混合物中的2,5-呋喃二羧酸与乙二醇的摩尔比 为1：1.01〜1：1.15，其中在蒸馏系统中除去在2,5-呋喃二甲酸与乙二醇的反应期间形成的水和一些乙二醇，并且其中用水除去的乙二醇， 与水分离，至少部分回收利用。

公开(公告)号：US20170015781A1

公开(公告)日：2017-01-19

申请号：US15123804

申请日：2015-03-11

Applicant: Furanix Technologies B.V.

Inventor： Jeffrey John Kolstad ,  Gerardus Johannes Maria Gruter ,  Matheus Adrianus Dam ,  Jesper Gabriël van Berkel ,  Robert Joseph Schiavone ,  Marion L. Andrews

IPC: C08G63/88 ,  C08G63/16 ,  C08G63/80 ,  C08G63/86

CPC classification number: C08G63/88 ,  C08G63/16 ,  C08G63/181 ,  C08G63/80 ,  C08G63/866

Abstract: 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.

Abstract translation: 通过在（Tm-40℃）范围内的温度下加热具有熔点Tm的半结晶起始聚酯来增强包含2,5-呋喃二甲酸乙二酯单元的半结晶起始聚酯的分子量， 以获得固体聚酯，其中半结晶起始聚酯的特性粘度为至少0.45dL / g，羧酸端基量在15至122meq / kg的范围内。

公开(公告)号：US09434708B2

公开(公告)日：2016-09-06

申请号：US14369485

申请日：2012-12-27

Applicant: Furanix Technologies B.V.

Inventor： Ana Sofia Vagueiro De Sousa Dias ,  Jan Cornelis Van Der Waal ,  Etienne Mazoyer

IPC: C07D307/48 ,  B01J21/08 ,  B01J29/08 ,  B01J29/18 ,  B01J29/40 ,  B01J29/60 ,  B01J29/70

CPC classification number: C07D307/48 ,  B01J21/08 ,  B01J29/08 ,  B01J29/18 ,  B01J29/40 ,  B01J29/60 ,  B01J29/7003 ,  B01J29/7007

Abstract: 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.

Abstract translation: 在进行反应的过程中，将液体反应混合物与包括二氧化硅和/或硅酸盐的催化剂接触，其中在接触之前将可溶于液体反应混合物的硅化合物加入到反应混合物中 与催化剂。 含水反应混合物适当地含有水，醇或其混合物。

公开(公告)号：US20160207898A1

公开(公告)日：2016-07-21

申请号：US14914972

申请日：2014-08-29

Applicant: FURANIX TECHNOLOGIES B.V.

Inventor： Jagdeep SINGH ,  Benjamin MCKAY ,  Bing WANG ,  Matheus Adrianus DAM ,  Gerardus Johannes Maria GRUTER ,  Ana Sofia Vagueiro DE SOUSA DIAS

IPC: C07D307/68 ,  C07B63/02

CPC classification number: C07D307/68 ,  C07B63/02

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.

Abstract translation: 包含2-甲酰基 - 呋喃-5-羧酸和2,5-呋喃二羧酸的酸组合物在包括以下步骤的方法中纯化： 使酸组合物与醇接触以获得酯化组合物; 并从酯化组合物中分离出2-甲酰基 - 呋喃-5-羧酸的酯，得到纯化的酯化产物; 并将纯化的酯化组合物与水接触以进行皂化或水解，得到包含2,5-呋喃二甲酸和减少量的2-甲酰基 - 呋喃-5-羧酸的产物组合物。