Copolyesters comprising 1,4-cyclohexanedimethanol produced with germanium catalyst

Patent metadata

Field	Value
Publication number	US-2025034328-A1
Application number	US-202218688147-A
Country	US
Kind code	A1
Filing date	Aug 25, 2022
Priority date	Aug 31, 2021
Publication date	Jan 30, 2025
Grant date	—

Abstract

A copolyester is provided comprising: a. at least one terephthalate acid residue; b. about 85 to about 96 mole % of ethylene glycol residues; c. about 4 to about 15 mole % of a combination of 1,4-cyclohexanedimethanol residues (CHDM) and diethylene glycol (DEG) residues; and d. a germanium catalyst present in the copolyester at a concentration of about 5 to about 500 ppm based on elemental germanium; wherein the terephthalate monomer is based on the substantially equal diacid equivalents of 100 mole % to diol equivalence of 100 mole % for a total of 200 mole %.

First claim

That which is claimed is:

1 . A copolyester comprising:
a. at least one terephthalate acid residue; b. about 85 to about 96 mole % of ethylene glycol residues; c. about 4 to about 15 mole % of a combination of 1,4-cyclohexanedimethanol residues (CHDM) and diethylene glycol (DEG) residues; and d. a germanium catalyst present in the copolyester at a concentration of about 5 to about 500 ppm based on elemental germanium; wherein the terephthalate monomer is based on the substantially equal diacid equivalents of 100 mole % to diol equivalence of 100 mole % for a total of 200 mole %.

2 . The copolyester of claim 1 wherein said terephthalic acid residues are from at least one monomer selected from the group consisting of terephthalic acid and dimethyl terephthalate.

3 . The copolyester of claim 1 further comprising a dicarboxylic acid selected from aliphatic dicarboxylic acids having 3 to 12 carbon atoms, cycloaliphatic dicarboxylic acids having 8 to 14 carbon atoms and aromatic dicarboxylic acids having 8 to 16 carbon atoms.

4 . The copolyester of claim 2 wherein said terephthalic acid residues in said copolyester range from 70 to 100 mole %.

5 . The copolyester of claim 1 further comprising up to 10 mole % of one or more modifying aromatic dicarboxylic acids.

6 . The copolyester of claim 1 further comprising up to 10 mole % of one or more aliphatic dicarboxylic acids containing 2-16 carbon atoms.

7 . The copolyester of claim 1 further comprising at least one additional aliphatic, alicyclic, and aralkyl glycol.

8 . The copolyester of claim 1 wherein the amount of ethylene glycol residues ranges from about 85 to about 92 mol %.

9 . The copolyester of claim 1 wherein said copolyester comprises about 4 to about 12 mole % of a combination of diethylene glycol (DEG) residues and 1,4-cyclohexanedimethanol residues (CHDM).

10 . The copolyester of claim 1 wherein the amount of germanium present in the copolyester is at a concentration of about 5 to about 450 ppm.

11 . The copolyester according to claim 1 wherein the glycol component of the polyester portion of said copolyester further comprises up to 10 mole % of one or more modifying glycols which are not 2,2,4,4-tetramethyl-1,3-cyclobutanediol, ethylene glycol, diethylene glycol, 1,4-cyclohexanedimethanol, or monopropylene glycol.

12 . The copolyester according to claim 11 wherein said modifying glycol is at least one selected from the group consisting of 1,2-propanediol, 1,3-propanediol, neopentyl glycol, isosorbide, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, p-xylene glycol, polytetramethylene glycol and mixtures thereof.

13 . The copolyester according to claim 1 further comprising at least one branching monomer.

14 . The copolyester according to claim 1 further comprising at least one chain extender.

15 . The copolyester according to claim 1 wherein said copolyester is capable of being recycled.

16 . The copolyester according to claim 1 having a crystallization half life of greater than 1 minute at 140° C.

17 . The copolyester according to claim 1 having a crystallization half life of greater than 2 minutes at 140° C.

18 . The copolyester according to claim 1 having a crystallization half life of greater than 3 minutes at 140° C.

19 . The copolyester according to claim 1 having a crystallization half life of greater than 1 minute at 140° C., 160° C., and 180° C.

20 . A copolyester comprising:
a. terephthalate acid residues; b. about 85 to about 96 mole % of ethylene glycol residues; c. about 4 to about 15 mole % of a combination of diethylene glycol (DEG) residues and 1,4-cyclohexanedimethanol residues (CHDM); and d. a germanium catalyst present in the copolyester at a concentration of about 5 to about 500 ppm based on elemental germanium; wherein the terephthalate monomer is based on the substantially equal diacid equivalents of 100 mole % to diol equivalence of 100 mole % for a total of 200 mole %; wherein said copolyester has a crystallization half life of greater than 1 minute at 140° C.

Assignees

• Eastman Chem Co

Inventors

• Cannon Joshua Seth
• Fleenor Coralie Mckenna
• George Scott Ellery
• Hu Huamin
• Treece Mark Allan
• Vogel Carolin Adleheid
• Kita Matthew Robert
• Woods Jason Scott
• Horton Jonathan Michael

Classifications

• B29K2995/0037

  Other properties · CPC title

• B29K2995/0026

  Transparent · CPC title

• B29K2067/003

  PET, i.e. poylethylene terephthalate · CPC title

• B29C48/022

  characterised by the choice of material · CPC title

• B29C48/0017

  combined with blow-moulding or thermoforming · CPC title