FDCA-based polyesters

• US 9,580,594 B2
• Filed: 12/18/2013
• Issued: 02/28/2017
• 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): JONES JR., ROBERT STOCKTON
• Application Number:
  US14/653,599
• Publication Number:
  US 20150307704A1
• Time in Patent Office: 1,168 Days
• US Class Current: 1/1
• CPC Class Codes: B29B 7/007 for continuous mixing
• CPC Class Codes: B29B 7/88 Adding charges , i.e. additives
• CPC Class Codes: B29C 48/0018 combined with shaping by orienting, stretching or shrinking, e.g. film blowing B29C48/0017 takes precedence
• CPC Class Codes: B29C 48/022 characterised by the choice of material
• CPC Class Codes: B29C 48/07 Flat, e.g. panels
• CPC Class Codes: B29C 48/08 flexible, e.g. films
• CPC Class Codes: B29C 48/911 Cooling
• CPC Class Codes: B29C 48/914 cooling drums
• CPC Class Codes: B29K 2067/00 Use of polyesters or derivatives thereof, as moulding material
• CPC Class Codes: B29K 2995/0067 non-permeable
• CPC Class Codes: B29L 2007/008 Wide strips, e.g. films, webs
• CPC Class Codes: C08G 63/16 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C08G 63/181 Acids containing aromatic rings
• CPC Class Codes: C08G 63/199 Acids or hydroxy compounds containing cycloaliphatic rings
• CPC Class Codes: C08J 2367/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds; C08J2367/06 takes precedence
• CPC Class Codes: C08J 2467/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C08J2467/06 takes precedence
• CPC Class Codes: C08J 5/18 Manufacture of films or sheets
• CPC Class Codes: C08L 2203/16 used for films
• CPC Class Codes: C08L 2205/025 containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
• CPC Class Codes: C08L 67/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C08L67/06 takes precedence
• CPC Class Codes: C08L 67/04 : Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence

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.

Claims

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 C₁ to C₁₀ 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 C₁ to C₁₀ 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 C₁ to C₁₀ alkyl diester of FDCA and 90 to 10 mole % of one or more C₁ to C₁₀ 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, C₁ to C₁₀ 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, C₁ to C₁₀ 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.