Glycolide-based polyesters made with isosorbide

Patent metadata

Field	Value
Publication number	US-9394402-B2
Application number	US-201314653701-A
Country	US
Kind code	B2
Filing date	Dec 18, 2013
Priority date	Dec 20, 2012
Publication date	Jul 19, 2016
Grant date	Jul 19, 2016

Abstract

A polymer comprises reaction product of (a) one or more diacid, diester thereof, or glycolide, and (b) one or more polyol, wherein component (a) comprises glycolide or combinations thereof, and component (b) consists essentially of isosorbide. A film or sheet having one or more layers, wherein at least one layer comprising a polymer comprises reaction product of (a) one or more diacid, diester thereof, or glycolide, and (b) one or more polyol, wherein component (a) comprises glycolide or combinations thereof, and component (b) consists essentially of isosorbide.

First claim

What is claimed is:

1. A polymer comprising the reaction product of (a) (i) glycolide and (ii) 2,5-furan dicarboxylic acid (FDCA), one or more C 1 to C 10 alkyl diester thereof, 2,6-napthalene dicarboxylic acid (NDCA), C 1 to C 10 alkyl diester thereof, or combinations thereof, and (b) a polyol, wherein the polyol consists of isosorbide.

2. The polymer of claim 1 wherein component (a) comprises 2 to 98 mol.%, based on the total weight of component (a), of glycolide, and 2 to 98 mol.%, based on the total amount of component (a), of C 1 to C 10 alkyl diesters of FDCA or NDCA, or combinations thereof.

3. A composition comprising a first polymer of claim 1 and 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 component (i) acids, esters or glycolide, and component (ii) polyols, wherein (x) component (i) does not include glycolide when component (ii) is isosorbide, and (y) wherein component (ii) does not include isosorbide when component (i) comprises glycolide.

4. The composition of claim 3 wherein at least one first polymer is the reaction product of glycolide with or without one or more C 1 to C 10 alkyl diesters of FDCA or NDCA, and at least one other polymer is the reaction product of glycolide and one more C 1 to C 10 alkyl diesters of FDCA or NDCA different from the diesters (if any) or combination of diesters (if any) present in the first polymer.

5. The composition of claim 3 wherein the other polyester (B) comprises a reaction product of component (i) and component (ii), where component (i) is selected from the group consisting of FDCA, one or more C 1 to C 10 alkyl diester thereof, NDCA, C 1 to C 10 alkyl diester thereof, or glycolide, or combinations thereof, and component (ii) is 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; provided that when component (i) comprises glycolide, component (ii) does not include isosorbide.

6. The composition of claim 3 wherein the other polyester comprises aliphatic homopolymer polyglycolide or polyglycolic acid (PGA), 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.

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

8. A film or sheet of one or more layers, wherein at least one layer comprises polymer comprising the reaction product of (a) (i) glycolide and (ii) 2,5-furan dicarboxylic acid (FDCA), one or more C 1 to C 10 alkyl diester thereof, 2,6-napthalene dicarboxylic acid (NDCA), C 1 to C 10 alkyl diester thereof, or combinations thereof, and (b) a polyol, wherein the polyol consists of isosorbide.

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

wherein the polymer comprises the reaction product of (a) (i)glycolide and (ii) 2,5-furan dicarboxylic acid (FDCA), one or more C 1 to C 10 alkyl diester thereof, 2,6-napthalene dicarboxylic acid (NDCA), C 1 to C 10 alkyl diester thereof, or combinations thereof, and (b) a polyol, wherein the polyol consists of isosorbide.

10. The method of claim 9 comprising the further step of orienting the film or sheet in the machine or cross direction, or both.

Assignees

• Dow Global Technologies Llc

Inventors

• Bhattacharjee Debkumar
• Sehanobish Kalyan

Classifications

• B29C47/0021

  Operations & Transport · mapped topic

• C08L2203/16

  used for films · CPC title

• C08L2201/14

  Gas barrier composition · CPC title

• C08G63/664

  derived from hydroxy carboxylic acids · CPC title

• C08J2367/04

  Polyesters derived from hydroxy carboxylic acids, e.g. lactones (C08J2367/06 takes precedence) · CPC title