IP Library Granted Patent US 9,777,111
Granted Patent B2
US 9,777,111 · App. 11/254,407 · Granted Oct 3, 2017

PET polymer with improved properties

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,777,111
App. No.
11/254,407
Granted
Oct 3, 2017
Kind
B2
Abstract

Polyester compositions having desirable injection molding properties and that retain good crystallization rates and natural stretch ratio characteristics are described. These polyesters are suitable for the manufacture of beverage containers, bulk continuous filaments, and other articles that can benefit from such improved properties.

Claims (56)

1. A polyester comprising:

i) a carboxylic acid component comprising at least 90 mol % terephthalic acid residues and from 0 to 10 mol % of carboxylic acid comonomer residues, wherein the carboxylic acid comonomer is selected from the group consisting of phthalic acid, isophthalic acid, a (C 1 -C 4 ) dialkyl ester of isophthalic acid, naphthalene-2,6-dicarboxylic acid, a (C 1 -C 4 ) dialkyl ester of naphthalene-2-6-dicarboxylic acid, cyclohexanedicarboxylic acid, cyclohexanediacetic acid, diphenyl-4,4′-dicarboxylic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, and sebacic acid;

ii) a hydroxyl component comprising at least 90 mol % ethylene glycol residues and additional hydroxyl residues in an amount of 1-10 mol %; wherein the additional hydroxyl residues comprise mixtures of diethylene glycol residues and hydroxyl comonomer residues, wherein said hydroxyl comonomer residues comprise 1,4-cyclohexanedimethanol;

based on 100 mol % of carboxylic acid component residues and 100 mol % of hydroxyl component residues in the polyester;

wherein at least one of the carboxylic acid and hydroxyl components comprises comonomer residues, the molar ratio of the total comonomer 1,4-cyclohexanedimethanol residues to diethylene glycol residues being 1.3:1.0 or greater; and

wherein the polyester comprises less than 2.3 mol % of diethylene glycol and has an intrinsic viscosity greater than 0.40 dL/g and less than 0.77 dL/g,

wherein the polyester has a degree of crystallization of at least 15%, and

wherein the polyester is in the form of pellets.

2. A polyester according to claim 1 , wherein the carboxylic acid comonomer is selected from the group consisting of isophthalic acid and naphthalene 2-6-dicarboxylic acid.

3. A polyester according to claim 1 , wherein the polyester comprises less than 2.0 mol % of diethylene glycol.

4. A polyester according to claim 3 , wherein the polyester comprises less than 1.6 mol % of diethylene glycol.

5. A polyester according to claim 1 , wherein the molar ratio of the total comonomer 1,4-cyclohexanedimethanol residues to diethylene glycol residues is 1.5:1.0 or greater.

6. A polyester according to claim 1 , wherein the polyester is prepared from 75% wt or greater virgin raw materials.

7. A polyester according to claim 1 , wherein the residual acetaldehyde content of the polyester is less than 2 ppm.

8. A polyester according to claim 7 , wherein the residual acetaldehyde content of the polyester is less than 1 ppm.

9. A polyester according to claim 1 , wherein the polyester has an intrinsic viscosity greater than 0.65 dL/g and less than 0.77 dL/g.

10. A polyester according to claim 1 , wherein the polyester has an intrinsic viscosity greater than 0.65 dL/g and less than 0.76 dL/g.

11. A polyester according to claim 1 , wherein the carboxylic acid component comprises from 1 to 10 mol % of carboxylic acid comonomer or the hydroxyl component comprises from 1 to 10 mol % of additional hydroxyl residues.

12. A polyester according to claim 11 , wherein the carboxylic acid component comprises from 3 to 10 mol % of carboxylic acid comonomer or the hydroxyl component comprises from 3 to 10 mol % of additional hydroxyl residues.

13. A polyester according to claim 1 ,

the molar ratio of the total comonomer 1,4-cyclohexanedimethanol residues to diethylene glycol residues is 1.5:1.0 or greater; and

wherein the polyester comprises less than 1.6 mol % of diethylene glycol and has an intrinsic viscosity of less than 0.76 dL/g.

14. A process for producing a container comprising:

feeding the polyester pellets of claim 1 to an extrusion zone;

melting the polyester pellets;

forming a sheet or molded part from the molten extruded polyester; and processing the sheet or molded part to make a container.

15. A polyester comprising:

i) a carboxylic acid component comprising 100 mol % terephthalic acid residues;

ii) a hydroxyl component comprising at least 90 and less than 95 mol % ethylene glycol residues and additional hydroxyl residues in an amount greater than 5 and up to 10 mol %; wherein the additional hydroxyl residues are diethylene glycol residues and hydroxyl comonomer residues;

based on 100 mol % of carboxylic acid component residues and 100 mol % of hydroxyl component residues in the polyester;

wherein the molar ratio of the hydroxyl comonomer residues to diethylene glycol residues is 1.3:1.0 or greater; and

wherein the polyester comprises less than 2.3 mol % of diethylene glycol and has an intrinsic viscosity greater than 0.40 dL/g and less than 0.80 dL/g,

wherein the polyester has a degree of crystallization of at least 15% %, and

wherein the polyester is prepared from 75% wt or greater virgin raw materials and is in the form of pellets.

16. A polyester according to claim 15 , wherein the hydroxyl comonomer is selected from the group consisting of triethylene glycol, 1,4-cyclohexanedimethanol, propane-1,3-diol, butane-1,4-diol, pentane-1,5-diol, hexane-1,6-diol, 3-methylpentanediol-(2,4), 2-methylpentanediol-(1,4), 2,2,4-trimethylpentane-diol-(1,3), 2,5-ethylhexanediol-(1,3), 2,2-diethyl propane-diol-(1,3), hexanediol-(1,3), 1,4-di-(hydroxyethoxy)-benzene, 2,2-bis-(4-hydroxycyclohexyl)-propane, 2,4-dihydroxy-1,1,3,3-tetramethyl-cyclobutane, 2,2-bis-(3-hydroxyethoxyphenyl)-propane, and 2,2-bis-(4-hydroxypropoxyphenyl)-propane.

17. A polyester according to claim 16 , wherein the hydroxyl comonomer is cyclohexane dimethanol.

18. A polyester according to claim 15 , wherein the polyester comprises less than 2.0 mol % of diethylene glycol.

19. A polyester according to claim 18 , wherein the polyester comprises less than 1.6 mol % of diethylene glycol.

20. A polyester according to claim 15 , wherein the molar ratio of the hydroxyl comonomer residues to diethylene glycol residues is 1.5:1.0 or greater.

21. A polyester according to claim 15 , wherein the acetaldehyde content of the polyester is less than 2 ppm.

22. A polyester according to claim 21 , wherein the acetaldehyde content of the polyester is less than 1 ppm.

23. A polyester according to claim 15 , wherein the polyester has an intrinsic viscosity greater than 0.65 dL/g and less than 0.78 dL/g.

24. A polyester according to claim 15 , wherein the polyester has an intrinsic viscosity greater than 0.65 dL/g and less than 0.76 dL/g.

25. A polyester according to claim 15 ,

wherein the molar ratio of the hydroxyl comonomer residues to diethylene glycol residues is 1.5:1.0 or greater; and

wherein the polyester comprises less than 1.6 mol % of diethylene glycol and has an intrinsic viscosity of less than 0.76 dL/g.

26. A process for producing a container comprising:

feeding the polyester pellets of in claim 15 to an extrusion zone;

melting the polyester pellets zone;

forming a sheet or molded part from the molten extruded polyester; and

processing the sheet or molded part to make a container.

27. A polyester according to claim 1 , wherein said carboxylic acid comonomer residues comprise isophthalic acid and/or naphthalene-2-6-dicarboxylic acid.

28. The polyester of claim 1 , wherein the polyester has a degree of crystallization of at least 35% zone.

29. The polyester of claim 1 , wherein the polyester has a degree of crystallization of at least 40%.

30. The polyester of claim 15 , wherein the polyester has a degree of crystallization of at least 35%.

31. The polyester of claim 15 , wherein the polyester has a degree of crystallization of at least 40%.

Assignments (3)
CHANGE OF NAME Recorded Jan 11, 2022
From: GRUPO PETROTEMEX, S.A. DE C.V.
To: ALPEK POLYESTER, S.A. DE C.V.
Reel/Frame 058691/0337 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2011
From: EASTMAN CHEMICAL COMPANY
To: GRUPO PETROTEMEX, S.A. DE C.V.
Reel/Frame 025727/0963 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 29, 2005
From: COLHOUN, FREDERICK LESLIE; MURDAUGHT, PERRY MICHAEL
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 017074/0634 →