Bio-based MEG and polyester fiber compositions and methods of making the same

Patent metadata

Field	Value
Publication number	US-11352718-B2
Application number	US-201716348407-A
Country	US
Kind code	B2
Filing date	Nov 9, 2017
Priority date	Nov 9, 2016
Publication date	Jun 7, 2022
Grant date	Jun 7, 2022

Abstract

Disclosed are bio-based polyester fibers, particularly a PET fibers, and a method of making the same by: contacting bio-based MEG composition with a diacid composition to form a polyester composition; and spinning and/or drawing the resulting polyester composition into a fiber; wherein the bio-based MEG composition comprises: a) monoethylene glycol (MEG); and b) from about 1 ppm to about 5000 ppm of at least one C3-Cy2 1,2-diol, wherein the C3-Cj2 1, 2-diol is linear, branched, or cyclic.

First claim

What is claimed is:

1. A method of making a bio-based polyester fiber comprising the steps of:
contacting a bio-based MEG composition with a diacid composition to form a polyester composition; and
spinning and/or drawing the resulting polyester composition into a fiber; wherein the bio-based MEG composition comprises: a) monoethylene glycol (MEG); and b) from about 1 ppm to about 5000 ppm of 1,2-propanediol, 1,2-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-cyclopentanediol, and 2-[(5-methyltetrahydro-2-furanyl)methoxy]ethanol.

2. The method according to claim 1 , wherein the bio-based MEG composition comprises from about 1 to about 1000 ppm of 1,2-propanediol.

3. The method according to claim 1 , wherein the bio-based MEG composition comprises from about 1 to about 1000 ppm of 1,2-butanediol.

4. The method according to claim 1 , wherein the bio-based MEG composition comprises from about 1 to about 1000 ppm of 1,2-pentanediol.

5. The method according to claim 1 , wherein the bio-based MEG composition comprises from about 1 to about 1000 ppm of 1,2-hexanediol.

6. The method according to claim 1 , wherein the bio-based MEG composition comprises from about 1 to about 1000 ppm of 1,2-cyclopentanediol.

7. The method according to claim 1 , wherein the bio-based MEG composition comprises from about 1 to about 1000 ppm of 2-[(5-methyltetrahydro-2-furanyl)methoxy] ethanol.

8. The method according to claim 1 , wherein the bio-based MEG composition comprises:
from about 1 to about 20 ppm of 1,2-propanediol;
from about 1 to about 80 ppm of 1,2-butanediol;
from about 1 to about 500 ppm of 1,2-pentanediol;
from about 1 to about 20 ppm of 1,2-hexanediol;
from about 1 to about 20 ppm of 1,2-cyclopentanediol; and
from about 1 to about 100 ppm of 2-[(5-methyltetrahydro-2-furanyl)methoxy] ethanol.

9. The method according to claim 1 , wherein the bio-based MEG composition comprises:
from about 5 to about 10 ppm of 1,2-propanediol;
from about 30 to about 70 ppm of 1,2-butanediol;
from about 300 to about 450 ppm of 1,2-pentanediol;
from about 5 to about 10 ppm of 1,2-hexanediol;
from about 5 to about 10 ppm of 1,2-cyclopentanediol; and/or from about 60 to about 80 ppm of 2-[(5-methyltetrahydro-2-furanyl)methoxy]ethanol.

10. The method according to claim 1 , wherein the diacid composition comprises terephthalic acid, isophthalic acid, 2,6-naphthalenedicarboxylic acid, 2,5-furandicarboxylic acid, 2-(2-carboxyphenyl)benzoic acid, or any combination thereof.

11. A bio-based polyester fiber produced according to the method of claim 1 .

12. A bio-based polyester fiber, comprising the polyester reaction product of:
a bio-based MEG composition comprising a) monoethylene glycol (MEG); and b) from about 1 ppm to about 5000 ppm of 1,2-propanediol, 1,2-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-cyclopentanediol, and 2-[(5-methyltetrahydro-2-furanyl)methoxy]ethanol; and
a diacid composition.

13. The bio-based polyester fiber according to claim 12 , wherein the bio-based MEG composition comprises:
from about 1 to about 1000 ppm of 1,2-propanediol;
from about 1 to about 1000 ppm of 1,2-butanediol;
from about 1 to about 1000 ppm of 1,2-pentanediol;
from about 1 to about 1000 ppm of 1,2-hexanediol;
from about 1 to about 1000 ppm of 1,2-cyclopentanediol; and from about 1 to about 1000 ppm of 2-[(5-methyltetrahydro-2-furanyl)methoxy]ethanol.

14. The bio-based polyester fiber according to claim 12 , wherein the bio-based MEG composition comprises:
from about 1 to about 20 ppm of 1,2-propanediol;
from about 1 to about 80 ppm of 1,2-butanediol;
from about 1 to about 500 ppm of 1,2-pentanediol;
from about 1 to about 20 ppm of 1,2-hexanediol;
from about 1 to about 20 ppm of 1,2-cyclopentanediol; and from about 1 to about 100 ppm of 2-[(5-methyltetrahydro-2-furanyl)methoxy]ethanol.

15. The bio-based polyester fiber according to claim 12 , wherein the diacid composition comprises terephthalic acid, isophthalic acid, 2,6-naphthalenedicarboxylic acid, 2-(2-carboxyphenyl)benzoic acid, or any combination thereof.

16. The bio-based polyester fiber according to claim 12 , wherein the polyester reaction product has a zero shear rate viscosity of from about 890 to about 1700 Pa·s.

17. The bio-based polyester fiber according to claim 12 , wherein the fiber has an intrinsic viscosity of from about 0.4 to about 2.0.

18. The bio-based polyester fiber according to claim 12 , wherein the fiber has a Denier per filament of from about 0.5 to about 40.

Assignees

• Coca Cola Co
• Changchun Meihe Science And Tech Development Co Ltd

Inventors

• Moffitt Ronald D
• Kriegel Robert
• Morales Marlon Salvador
• Ren Haiyu
• Yi Yang
• Liu Jing
• Qi Hongbin

Classifications

• C08G63/183 Primary

  Terephthalic acids · CPC title

• D01F6/62 Primary

  from polyesters · CPC title

• D01F6/84 Primary

  from copolyesters · CPC title

• C08G63/42

  Cyclic ethers (C08G59/00 takes precedence); Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters · CPC title

• C08G63/181

  Acids containing aromatic rings · CPC title