Polyester compositions which comprise cyclobutanediol and certain thermal stabilizers, and/or reaction products thereof

Patent metadata

Field	Value
Publication number	US-9765203-B2
Application number	US-201514869705-A
Country	US
Kind code	B2
Filing date	Sep 29, 2015
Priority date	Mar 28, 2006
Publication date	Sep 19, 2017
Grant date	Sep 19, 2017

Abstract

Described as one aspect of the invention are polyester compositions containing:
(I) at least one polyester which comprises:
(a) a dicarboxylic acid component comprising:
(i) 70 to 100 mole % of terephthalic acid residues; (ii) 0 to 30 mole % of aromatic dicarboxylic acid residues having up to 20 carbon atoms; and (iii) 0 to 10 mole % of aliphatic dicarboxylic acid residues having up to 16 carbon atoms; and
(b) a glycol component comprising:
(i) 1 to 99 mole % of 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues; and (ii) 1 to 99 mole % of cyclohexanedimethanol residues; and

(II) at least one thermal stabilizer chosen from at least one of alkyl phosphate esters, aryl phosphate esters, mixed alkyl aryl phosphate esters, reaction products thereof, and mixtures thereof;

wherein the total mole % of the dicarboxylic acid component is 100 mole %, and

wherein the total mole % of the glycol component is 100 mole %.

First claim

What is claimed is:

1. A polyester composition comprising:
(I) at least one polyester which comprises:
a) a dicarboxylic acid component comprising:
i) 80 to 100 mole % of terephthalic acid residues;
ii) 0 to 20 mole % of aromatic dicarboxylic acid residues having up to 20 carbon atoms; and
iii) 0 to 10 mole % of aliphatic dicarboxylic acid residues having up to 16 carbon atoms; and

(b) a glycol component comprising:
i) 30 to 40 mole % of 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues; and
ii) 60 to 70 mole % of cyclohexanedimethanol residues, and

(II) at least one thermal stabilizer chosen from at least one of alkyl phosphate esters, aryl phosphate esters, mixed alkyl aryl phosphate esters, reaction products thereof, or mixtures thereof;

wherein the total mole % of the dicarboxylic acid component is 100 mole %, and the total mole % of the glycol component is 100 mole %; and
wherein the inherent viscosity of said polyester is from 0.55 to 0.68 dL/g as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.25 g/50 ml at 25° C.;
wherein said polyester has a Tg from 110 to 150° C.;
wherein the ratio of total tin atoms to total phosphorus atoms in the final polyester is from 5-9:1; and
wherein said polyester composition contains no polycarbonate.

2. The composition of claim 1 , wherein the inherent viscosity of said polyester is from 0.60 to 0.68 dL/g.

3. The composition of claim 1 , wherein said polyester has a Tg of 110 to 130° C.

4. The composition of claim 1 , wherein said polyester has a Tg of 110 to 125° C.

5. The composition of claim 1 , wherein the dicarboxylic acid component comprises 90 to 100 mole % of terephthalic acid residues.

6. The polyester composition of claim 1 , wherein the polyester comprises from 0.01 to 10 mole % of ethylene glycol.

7. The composition of claim 1 , wherein said 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues is a mixture comprising from 40 to 60 mole % of cis-2,2,4,4-tetramethyl-1,3-cyclobutanediol residues and from 40 to 60 mole % of trans-2,2,4,4-tetramethyl-1,3-cyclobutanediol residues.

8. The composition of claim 1 , wherein said polyester composition further comprises at least one polymer chosen from at least one of the following: nylons; polyesters other than those of claim 1 ; polyamides; polystyrene; polystyrene copolymers; styrene acrylonitrile copolymers; acrylonitrile butadiene styrene copolymers; poly(methylmethacrylate); acrylic copolymers; poly(ether-imides); polyphenylene oxides; or poly(phenylene oxide)/polystyrene blends; polyphenylene sulfides; polyphenylene sulfide/sulfones; polysulfones; polysulfone ethers; poly(ether-ketones) of aromatic dihydroxy compounds; or mixtures thereof.

9. The composition of claim 1 , wherein said polyester comprises residues of at least one branching agent for the polyester.

10. The composition of claim 1 , wherein said polyester comprises residues of at least one branching agent in an amount of 0.01 to 5 weight % based on the total mole percentage of the acid or glycol residues.

11. The composition of claim 1 , wherein said 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues is a mixture comprising greater than 50 mole % of cis-2,2,4,4-tetramethyl-1,3-cyclobutanediol residues.

12. The composition of claim 1 , wherein said polyester composition comprises at least one thermal stabilizer, reaction products thereof, and/or mixtures thereof chosen from at least one aryl phosphate ester.

13. The composition of claim 1 , wherein said polyester composition comprises at least one thermal stabilizer, reaction products thereof, and/or mixtures thereof chosen from at least one triaryl phosphate ester.

14. The composition of claim 1 , wherein said polyester composition of the invention may comprise at least one alkyl phosphate ester.

15. The composition of claim 1 , wherein said polyester composition comprises at least one thermal stabilizer, reaction products thereof, and/or mixtures thereof comprising triphenyl phosphate.

16. The composition of claim 1 , wherein said 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues is a mixture comprising greater than 55 mole % of cis-2,2,4,4-tetramethyl-1,3-cyclobutanediol residues.

17. The composition of claim 1 , wherein said 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues is a mixture comprising greater than 70 mole % of cis-2,2,4,4-tetramethyl-1,3-cyclobutanediol residues.

18. An article of manufacture comprising the polyester composition of claim 1 .

Assignees

• Eastman Chem Co

Inventors

• Germroth Ted Calvin
• Connell Gary Wayne
• Crawford Emmett Dudley
• Pecorini Thomas Joseph
• Mcwilliams Douglas Stephens
• Barton Benjamin Fredrick
• Shackelford Damon Bryan

Classifications

• C08G63/199

  Acids or hydroxy compounds containing cycloaliphatic rings · CPC title

• C08K5/523 Primary

  with hydroxyaryl compounds · CPC title

• C08L79/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C08L67/02

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

• C08G63/82

  characterised by the catalyst used · CPC title