Polymers containing aromatic dicarboxylic acid

Patent metadata

Field	Value
Publication number	US-11033851-B2
Application number	US-201916586944-A
Country	US
Kind code	B2
Filing date	Sep 28, 2019
Priority date	Mar 29, 2018
Publication date	Jun 15, 2021
Grant date	Jun 15, 2021

Abstract

A process is provided for making a polymer comprising providing a mixture of at least one furandicarboxylic acid, at least one diol, and at least one C2-C3 dicarboxlic acid, ester derivatives of C2-C3 dicarboxylic acid, hydroxy fatty acid or ester derivative of a hydroxy fatty acid; adding a catalyst and processing said mixture at reaction conditions until a polymer product is produced. The polymer consists of random units based upon the starting materials that are used.

First claim

The invention claimed is:

1. A reaction product of furandicarboxylic acid, at least one diol, and at least one C2-C3 dicarboxlic acid or hydroxy fatty acid with a catalyst.

2. The reaction product of claim 1 wherein said furandicarboxylic acid is an isomer selected from 2,5-furandicarboxylic acid, 2,4-furandicarboxylic acid, 2,3-furandicarboxylic acid or a diester of the acid selected from dimethyl ester furandicarboxylate or diethyl ester furandicarboxylate.

3. The polymer of claim 1 wherein said diol is an aliphatic hydrocarbon diol or a cyclicdiol and said C2-C3 dicarboxylic acid is oxalic acid or malonic acid or esters of said oxalic acid or malonic acid.

4. A process of making a polymer comprising
a. providing a mixture of at least one furandicarboxylic acid, at least one diol, and at least one C2-C3 dicarboxlic acid, ester derivatives of C2-C3 dicarboxylic acid, hydroxy fatty acid or ester derivative of a hydroxy fatty
b. adding a catalyst and
c. processing said mixture at reaction conditions comprising a pressure from less than ambient pressure to 100 atm until a polymer product is produced.

5. The process of claim 4 wherein said furandicarboxylic acid is an isomer of furandicarboxylic acid or a diester of furandicarboxylic acid.

6. The process of claim 4 wherein said isomer of furandicarboxylic is selected from 2,5-furandicarboxylic acid, 2,4-furandicarboxylic acid, and 2,3-furandicarboxylic acid.

7. The process of claim 5 wherein said diester of furandicarboxylic comprises dimethylester furandicarboxylate or diethyl ester furandicarboxylate.

8. The process of claim 4 wherein said diol is an aliphatic hydrocarbon diol, a cyclic diol or mixtures thereof.

9. The process of claim 4 wherein said aliphatic hydrocarbon diol is selected from ethylene glycol, propylene glycol, and butane diol said cyclic diol is cyclohexanediol.

10. The process of claim 4 wherein said C2-C3 dicarboxylic acid comprises oxalic acidor malonic acid or esters of said oxalic acid or malonic acid.

11. The process of claim 4 wherein said hydroxy fatty acid is selected from 3-hydroxyvaleric acid, 4-hydroxybutryic acid, ricinoleic acid, 12-hydroxymadecanoic acid, 16-hydroxyhexadecanoic acid, 17-hydroxyoctadecanoic acid, 9,10-epoxy-18-hydroxyoctadecanoic acid, and 9,10,18-trihydroxyoctadecanoic acid.

12. The process of claim 4 wherein said reaction conditions comprise a temperature from about 100° C. to 350° C.

13. The process of claim 4 wherein said catalysts are selected from metal oxides and metal alkoxide catalysts.

14. The process of claim 13 wherein said metal alkoxides are selected from titanium alkoxides, tin alkoxides, germanium alkoxides, antimony alkoxides and mixtures thereof.

15. The process of claim 13 wherein said metal alkoxide catalysts are selected from ethoxides, propoxides, isopropoxides, butoxides, iso-butoxides and tert-butoxides.

16. The process of claim 4 wherein said process has a duration of from 1 minute to 24 hours.

17. The process of claim 4 wherein said furandicarboxylic acid and said C2-C3 dicarboxylic acid or the hydroxy fatty acid are present at a mol ratio of from 0.01:1 to 1:0.1.

18. The process of claim 4 wherein said process is a continuous, semi batch or batch process.

Assignees

• Uop Llc

Inventors

• Broderick Erin Marie
• Lupton Francis Stephen
• Abrevaya Hayim

Classifications

• B01D2257/80

  Water · CPC title

• C08G63/16

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C10G53/08

  including at least one sorption step · CPC title

• C10G2300/207

  Acid gases, e.g. H2S, COS, SO2, HCN · CPC title

• B01D2252/204

  Amines · CPC title