Process for preparing a polymer having a 2,5-furandicarboxylate moiety within the polymer backbone and such (co)polymers

Patent metadata

Field	Value
Publication number	US-9765183-B2
Application number	US-201615203991-A
Country	US
Kind code	B2
Filing date	Jul 7, 2016
Priority date	Dec 30, 2008
Publication date	Sep 19, 2017
Grant date	Sep 19, 2017

Abstract

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. 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.

First claim

The invention claimed is:

1. A polymer having 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, and a reducing compound.

2. The polymer of claim 1 , wherein the reducing compound is a phosphorus compound.

3. The polymer of claim 2 , wherein the phosphorus compound is an organophosphorus compound.

4. The polymer of claim 2 , wherein the phosphorus compound is a monoalkyl or dialkyl phosphinate, a phosphonite or a phosphite.

5. The polymer of claim 2 , wherein the phosphorus compound is selected from the group consisting of triphenyl phosphite, diphenyl alkyl phosphite, phenyl dialkyl phosphite, tris(nonylphenyl)phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite, tris(2,4-di-tert-butylphenyl)phosphite, diisodecyl pentaerythritol diphosphite, di(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, tristearylsorbitol triphosphite, tetrakis(2,4-di-tert-butylphenyl) 4,4′-diphenylenediphosphonite, 4,4′-isopropylidenediphenol alkyl (C12-15) phosphite, poly(dipropylene glycol) phenyl phosphite, tetraphenyl dipropylene glycol phosphite, tetraphenyl diisopropylene glycol phosphite, trisisodecyl phosphite, diisodecyl-phenyl phosphite, diphenyl isodecyl phosphite, and mixtures of these.

6. The polymer of claim 1 , further comprising a diol moiety within the polymer backbone selected from the group consisting of ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,4-cyclohexanedimethanol, 1,6-hexanediol, 2,2-dimethyl-1,3-propanediol, poly(ethylene glycol), poly(tetrahydrofuran), glycerol, pentaerythritol.

7. The polymer of claim 1 , further having a 1,4-bis(hydroxymethyl)cyclohexane (cis, trans or both) moiety within the polymer backbone.

8. The polymer of claim 1 , further having a 2,2-dimethyl-1,3-propanediol moiety within the polymer backbone.

9. The polymer of claim 1 , further having a poly(ethylene glycol) moiety within the polymer backbone.

10. The polymer of claim 1 , further having a poly(tetrahydrofuran) moiety within the polymer backbone.

11. The polymer of claim 1 , further having a glycerol moiety within the polymer backbone.

12. The polymer of claim 1 , further having a pentaerythritol moiety within the polymer backbone.

13. The polymer of claim 1 , further having a lactic acid moiety within the polymer backbone.

14. The polymer of claim 1 , further having a 6-hydroxyhexanoic acid moiety within the polymer backbone.

Assignees

• Furanix Technologies Bv

Inventors

• Sipos Laszlo

Classifications

• C08K5/52

  Phosphorus bound to oxygen only · CPC title

• C08G63/80

  Solid-state polycondensation · CPC title

• C08G63/85 Primary

  Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof {(C08G63/823 takes precedence)} · CPC title

• C08G63/60

  derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds · CPC title

• C08G63/668

  derived from polycarboxylic acids and polyhydroxy compounds · CPC title