IP Library Granted Patent US 10,150,862
Granted Patent B2
US 10,150,862 · App. 15/307,995 · Granted Dec 11, 2018

Transesterified furan based polyesters and articles made therefrom

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Quick Facts
Patent No.
US 10,150,862
App. No.
15/307,995
Granted
Dec 11, 2018
Kind
B2
Abstract

Transesterified-blend compositions comprising transesterified furan-based polyester and transesterified terephthalate-based polyester disclosed herein and articles made therefrom.

Claims (37)

1. A composition comprising:

a. a transesterified furan-based polyester comprising first-alkylene furandicarboxylate repeat units (R 1 F) and one or more of a second-alkylene furandicarboxylate repeat unit (R 2 F), a first-alkylene terephthalate repeat unit (R 1 T), and a second-alkylene terephthalate repeat unit (R 2 T); and

b. a transesterified terephthalate-based polyester comprising second-alkylene terephthalate repeat unit (R 2 T) and one or more of a first-alkylene terephthalate repeat unit (R 1 T), a second-alkylene furan repeat unit (R 2 F), and a first-alkylene furandicarboxylate repeat units (R 1 F);

wherein the first-alkylene group (R 1 ) and the second-alkylene group (R 2 ) are independently selected from a C 2 to C 12 aliphatic group, and

wherein the composition has an NMR blockiness index of greater than 0.00 and less than 1.00.

2. The composition of claim 1 , wherein the composition shows a shift in one or more elution times as measured by interaction polymer chromatography, from at least one of:

a corresponding untransesterified furan-based polyester comprising the first-alkylene furandicarboxylate repeat units (R 1 F), or

a corresponding untransesterified terephthalate-based polyester comprising the second-alkylene terephthalate repeat unit (R 2 T), poly(second-alkylene terephthalate).

3. The composition of claim 1 , wherein the transesterified furan-based polyester is present in an amount in the range of 0.1-99.9 weight %, based on the total weight of the composition.

4. The composition of claim 1 , further comprises another transesterified furan-based polyester comprising a third-alkylene furandicarboxylate repeat unit (R 3 F), and one or more of a first-alkylene furandicarboxylate repeat unit (R 1 F), a second-alkylene furandicarboxylate repeat unit (R 2 F), a third-alkylene terephthalate repeat unit (R 3 T), and a second-alkylene terephthalate repeat unit (R 2 T),

wherein the third-alkylene group (R 3 ) is selected from a C 2 to C 12 aliphatic group.

5. The composition of claim 1 , further comprises another transesterified terephthalate-based polyester comprising a fourth-alkylene terephthalate repeat unit (R 4 T) and one or more of a first-alkylene terephthalate repeat unit (R 1 T), second-alkylene terephthalate repeat unit (R 2 T), a fourth-alkylene furandicarboxylate repeat unit (R 4 F), and a first-alkylene furandicarboxylate repeat unit (R 1 F),

wherein the fourth-alkylene group (R 4 ) is selected from a C 2 to C 12 aliphatic group.

6. The composition of claim 1 , wherein R 1 is a trimethylene group and R 2 is an ethylene group, such that:

i. the first-alkylene furandicarboxylate repeat unit (R 1 F) is trimethylene furandicarboxylate repeat unit (3F),

ii. the second-alkylene furandicarboxylate repeat units (R 2 F) is ethylene furandicarboxylate repeat units (2F),

iii. the first-alkylene terephthalate repeat unit (R 1 T) is trimethylene terephthalate repeat unit (3T),

iv. the second-alkylene terephthalate repeat unit (R 2 T) is ethylene terephthalate repeat unit (2T),

v. the transesterified furan-based polyester is transesterified poly(trimethylene furandicarboxylate) (t-PTF),

vi. the transesterified terephthalate-based polyester is transesterified poly(ethylene terephthalate) (t-PET), and

vii. the corresponding untransesterified furan-based polyester is poly(trimethylene furandicarboxylate) (PTF).

7. The composition of claim 1 further comprising an effective amount of a transesterification inhibitor or a transesterification catalyst.

8. An article comprising the composition of claim 1 , wherein the article is in the form of a sheet, a film or a molded article.

9. The article of claim 8 , wherein the composition provides a substantial gas barrier to at least one of oxygen, carbon dioxide or moisture.

10. The article according to claim 8 , wherein the article is a beverage container.

11. A multilayer structure comprising the composition of claim 1 in at least one of a barrier layer or a structural layer.

12. The multilayer structure of claim 11 , wherein the multilayer structure is in a form of a housing provided with a port for introducing a chemical in an enclosure defined by the housing.

13. The multilayer structure of claim 11 in a form of a hollow body selected from a group consisting of a hose, a pipe, a duct, a tube, a tubing or a conduit.

14. A method of improving gas barrier properties of a composition comprising a terephthalate-based polyester, comprises the step of:

melt blending 0.1-99.9% by weight of a poly(first-alkylene furandicarboxylate) (PR 1 F) with 0.1-99.9% by weight of a poly(second-alkylene terephthalate) (PR 2 T) at a melt blending temperature and a melt blending time to form a transesterified blend composition,

wherein the melt blending time is minimum time required for the transesterified blend composition to have a desired degree of transesterification, as determined by at least one of:

an NMR blockiness index of greater than 0.00 and less than 1.00, or

a shift in one or more IPC elution times from at least one of the poly(first-alkylene furandicarboxylate) or poly(second-alkylene terephthalate),

wherein the melt blending temperature is in the range of extrusion processing temperatures of the poly(first-alkylene furandicarboxylate) and the poly(second-alkylene terephthalate),

wherein the poly(first-alkylene furandicarboxylate) (PR 1 F) is derived from 2,5-furan dicarboxylic acid or a derivative thereof and at least one of a C 2 to C 12 aliphatic diol or a polyol monomer, and optionally at least one of a polyfunctional aromatic acid or a hydroxyl acid, and

wherein the poly(second-alkylene terephthalate) is derived from a terephthalic acid or a derivative thereof, a C 2 -C 12 aliphatic diol or a polyol monomer and optionally isophthalic acid or a derivative thereof.

15. The method of claim 14 , wherein the step of melt blending 0.1-99.9% by weight of a poly(first-alkylene furandicarboxylate) (PR 1 F) with 0.1-99.9% by weight of a poly(second-alkylene terephthalate) (PR 2 T) is carried out in the presence of an effective amount of a transesterification inhibitor or a transesterification catalyst to further control the transesterification, and thereby blockiness index.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2024
From: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
To: COVATION INC.
Reel/Frame 066376/0877 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 18, 2024
From: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
To: COVATION INC.
Reel/Frame 066350/0534 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ENTITY TYPE PREVIOUSLY RECORDED AT REEL: 049879 FRAME: 0043. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Sep 6, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
Reel/Frame 050300/0408 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
Reel/Frame 049879/0043 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 4, 2017
From: BRUN, YEFIM; CASTAGNA, ALICIA MARIE; LIAO, KEN-HSUAN; NEDERBERG, FREDRIK; MCCORD, ELIZABETH FORRESTER; RASMUSSEN, CHRISTOPHER JOHN
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 042236/0078 →