FDCA-based polyesters

Patent metadata

Field	Value
Publication number	US-9580594-B2
Application number	US-201314653599-A
Country	US
Kind code	B2
Filing date	Dec 18, 2013
Priority date	Dec 20, 2012
Publication date	Feb 28, 2017
Grant date	Feb 28, 2017

Abstract

A polymer comprising reaction product of (a) one or more diacid or diester thereof, and (b) one or more polyol, wherein component (a) comprises 5 to 100 mole %, based on the total amount of component (a), of 2,5-furan dicarboxylic acid (FDCA), or one or more C1 to C10 alkyl diester thereof, and component (b) comprises a mixture of 1,3-cyclohexanedimethanol and 1,4-cyclohexanedimethanol, or 2,2,4,4-tetramethyl-1,3-cyclobutanediol, or combinations thereof.

First claim

What is claimed is:

1. A polymer comprising reaction product of (a) one or more diacid or diester thereof, and (b) one or more polyol, wherein component (a) comprises 5 to 100 mole %, based on the total amount of component (a), of 2,5-furan dicarboxylic acid (FDCA), or one or more C 1 to C 10 alkyl diester thereof, and component (b) comprises 55-65 mole %, based on the total amount of component (b), of 1,3-cyclohexanedimethanol and 35-45 mole %, based on the total amount of component (b), of 1,4-cyclohexanedimethanol.

2. The polymer of claim 1 wherein component (a) comprises dimethyl furanoate (DMF).

3. The polymer of claim 1 wherein component (a) further comprises 0.1 to 95 mole %, based on the total amount of component (a), of 2,6-naphthalene dicarboxylic acid (NDCA), one or more C 1 to C 10 alkyl diester thereof.

4. The polymer of claim 3 wherein component (a) comprises dimethyl naphthanoate (DMN).

5. The polymer of claim 3 wherein component (a) comprises 10 to 90 mole % of FDCA and 90 to 10 mole % of NDCA, based on the total amount of component (a).

6. The polymer of claim 3 wherein component (a) comprises 10 to 90 mole % of one or more C 1 to C 10 alkyl diester of FDCA and 90 to 10 mole % of one or more C 1 to C 10 alkyl diester of NDCA, based on the total amount of component (a).

7. A composition comprising:
(1) a first polymer of claim 1 and
(2) one or more second polymer selected from the group consisting of:
(A) polymers of claim 1 different from the first polymer, and
(B) other polyesters which are reaction product of (i) acids or esters and (ii) polyols,
wherein:
(x) the acids and esters do not include FDCA, C 1 to C 10 alkyl diester thereof, or combinations thereof, when the polyol is a mixture of 1,3-cyclohexanedimethanol and 1,4-cyclohexanedimethanol, or 2,2,4,4-tetramethyl-1,3-cyclobutanediol, or combinations thereof, and
(y) the polyols do not include a mixture of 1,3-cyclohexanedimethanol and 1,4-cyclohexanedimethanol, or 2,2,4,4-tetramethyl-1,3-cyclobutanediol, or combinations thereof when the acids and esters are selected from the group consisting of FDCA, C 1 to C 10 alkyl diester thereof, or combinations thereof.

8. The composition comprising two or more polymers of claim 7 , wherein at least one polymer is the reaction product of a diacid and at least one other polymer is the reaction product of a diester.

9. The composition of claim 7 , wherein the other polyester comprises a reaction product of component (i) glycolic acid or glycolide, and component (ii) one or more polyol comprising a mixture of 1,3-cyclohexanedimethanol and 1,4-cyclohexanedimethanol, or 2,2,4,4-tetramethyl-1,3-cyclobutanediol, or combinations thereof.

10. The composition of claim 7 , wherein the other polyester comprises aliphatic homopolymer polyglycolide or polyglycolic acid (PGA), polylactide or polylactic acid (PLA), polycaprolactone (PCL), copolymer polyethylene adipate (PEA), polyhydroxyalkanoate (PHA), polyethylene terephthalate (PET), semi-aromatic copolymer PET, polybutylene terephthalate (PBT), polytrimethylene terephthalate (PTT), polyethylene naphthalate (PEN), and aromatic copolymers from polycondensation of 4-hydroxybenzoic acid and 6-hydroxynaphthalene-2-carboxylic acid.

11. An article comprising one or more polymers of claim 1 .

12. A method of forming a film or sheet comprising:
(i) extruding the polymer of claim 1 to form an extrudate;
(ii) shaping the extrudate by passing it through a flat or annular die; and
(iii) cooling the extrudate to form a film or sheet having a machine direction and a cross direction.

13. The method of claim 12 comprising the further step of orienting the film or sheet in the machine or cross direction, or both.

14. A film or sheet having one or more layers, wherein at least one layer comprises the polymer of claim 1 .

Assignees

• Dow Global Technologies Llc

Inventors

• Bhattacharjee Debkumar
• Sehanobish Kalyan

Classifications

• C08L2203/16

  used for films · CPC title

• B29C47/0057

  Operations & Transport · mapped topic

• C08L67/04

  Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C08L67/06 takes precedence) · CPC title

• C08L67/02 Primary

  Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence) · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title