Glycolide-based polyesters made with isosorbide

• US 9,394,402 B2
• Filed: 12/18/2013
• Issued: 07/19/2016
• Est. Priority Date: 12/20/2012
• Status: Expired due to Fees

• Current Assignee: Dow Global Technologies LLC (Dow, Inc.)
• Original Assignee: Dow Global Technologies LLC (Dow, Inc.)
• Inventors: Bhattacharjee, Debkumar, Sehanobish, Kalyan
• Primary Examiner(s): BOYKIN, TERRESSA M
• Application Number:
  US14/653,701
• Publication Number:
  US 20150337095A1
• Time in Patent Office: 944 Days
• Field of Search: 525/411, 528/271, 528/272
• US Class Current: 1/1
• CPC Class Codes: B29C 48/08 flexible, e.g. films
• CPC Class Codes: B29K 2067/00 Use of polyesters or derivatives thereof, as moulding material
• CPC Class Codes: B29L 2007/008 Wide strips, e.g. films, webs
• CPC Class Codes: C08G 63/60 derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
• CPC Class Codes: C08G 63/66 Polyesters containing oxygen in the form of ether groups C08G63/42, C08G63/58 take precedence
• CPC Class Codes: C08G 63/664 derived from hydroxy carboxylic acids
• CPC Class Codes: C08J 2367/00 Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
• CPC Class Codes: C08J 2367/04 Polyesters derived from hydroxy carboxylic acids, e.g. lactones C08J2367/06 takes precedence
• CPC Class Codes: C08J 5/18 Manufacture of films or sheets
• CPC Class Codes: C08L 2201/14 Gas barrier composition
• CPC Class Codes: C08L 2203/16 used for films
• CPC Class Codes: C08L 2666/18 Polyesters or polycarbonates according to C08L67/00 - C08L69/00; Derivatives thereof
• CPC Class Codes: C08L 67/00 Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain of polyester-amides C08L77/12; of polyester-imides C08L79/08; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence

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.

Claims

1. A polymer comprising the reaction product of (a) (i) glycolide and (ii) 2,5-furan dicarboxylic acid (FDCA), one or more C₁ to C₁₀ alkyl diester thereof, 2,6-napthalene dicarboxylic acid (NDCA), C₁ to C₁₀ 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 C₁ to C₁₀ 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 C₁ to C₁₀ alkyl diesters of FDCA or NDCA, and at least one other polymer is the reaction product of glycolide and one more C₁ to C₁₀ 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 C₁ to C₁₀ alkyl diester thereof, NDCA, C₁ to C₁₀ 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 C₁ to C₁₀ alkyl diester thereof, 2,6-napthalene dicarboxylic acid (NDCA), C₁ to C₁₀ 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 C₁ to C₁₀ alkyl diester thereof, 2,6-napthalene dicarboxylic acid (NDCA), C₁ to C₁₀ 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.