Certain polyester compositions which comprise cyclohexanedimethanol, moderate cyclobutanediol, cyclohexanedimethanol, and high trans cyclohexanedicarboxylic acid

• US 20070232779A1
• Filed: 02/14/2007
• Published: 10/04/2007
• Est. Priority Date: 03/28/2006
• Status: Abandoned Application

• Current Assignee: Eastman Chemical Company
• Original Assignee: Eastman Chemical Company
• Inventors: Crawford, Emmett Dudley, Moody, Leslie Shane, Lizotte, Jeremy R.
• Application Number:
  US11/706,791
• Publication Number:
  US 20070232779A1
• Time in Patent Office: Days
• US Class Current: 528/272
• CPC Class Codes: B32B 2270/00 Resin or rubber layer containing a blend of at least two different polymers
• CPC Class Codes: B32B 2307/558 Impact strength, toughness
• CPC Class Codes: B32B 2307/702 Amorphous
• CPC Class Codes: B32B 2419/00 Buildings or parts thereof walls, panels B32B2607/00
• CPC Class Codes: B32B 2457/20 Displays, e.g. liquid crystal displays, plasma displays
• CPC Class Codes: B32B 2551/00 Optical elements
• CPC Class Codes: B32B 2605/00 Vehicles
• CPC Class Codes: B32B 27/08 of synthetic resin
• CPC Class Codes: B32B 27/18 characterised by the use of special additives
• CPC Class Codes: B32B 27/36 comprising polyesters
• 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 5/18 Manufacture of films or sheets
• CPC Class Codes: C08L 101/00 Compositions of unspecified macromolecular compounds
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 67/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C08L67/06 takes precedence

Abstract

Described as one aspect of the invention are polyester compositions A polyester composition comprising at least one polyester which comprises:

• • (A) a dicarboxylic acid component comprising:
    • i) 70 to 100 mole % of cyclohexanedicarboxylic acid residues or an ester thereof comprising:
      • (a) 80 to 99 mole % trans-cyclohexanedicarboxylic acid residues or an ester thereof; and
      • (b) 1 to 20 mole % cis-cyclohexanedicarboxylic acid residues or an ester thereof;
    • ii) 0 to 30 mole % of aliphatic dicarboxylic acid residues, other than cyclohexanedicarboxylic acid residues, having up to 16 carbon atoms or esters thereof, other than cyclohexanedicarboxylic acid residues; and
    • iii) 0 to 10 mole % of aromatic dicarboxylic acid residues having up to 20 carbon atoms; and
  • (B) a glycol component comprising:
    • i) 5 to 35 mole % of 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues; and
    • ii) 65 to 95 mole % of 1,4-cyclohexanedimethanol residues, 1,3-cyclohexanedimethanol residues, 1,2-cyclohexanedimethanol residues or esters thereof or mixtures thereof,
      wherein the total mole % of said dicarboxylic acid component is equal to 100 mole %;
      the total mole % of said glycol component is equal to 100 mole %;
      wherein the inherent viscosity of said polyester is from 0.35 to 1.2 dL/g as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25° C.; and wherein said polyester has a Tg of from 66 to 120° C. The polyesters may be manufactured into articles.

Claims

1. A polyester composition comprising at least one polyester which comprises:

(A) a dicarboxylic acid component comprising;

i) 70 to 100 mole % of cyclohexanedicarboxylic acid residues or an ester thereof comprising;

(a) 70 to 98 mole % trans-cyclohexanedicarboxylic acid residues or an ester thereof; and

(b) 2 to 30 mole % cis-cyclohexanedicarboxylic acid residues or an ester thereof;

ii) 0 to 30 mole % of aliphatic dicarboxylic acid residues, other than cyclohexanedicarboxylic acid residues, having up to 16 carbon atoms or esters thereof, other than cyclohexanedicarboxylic acid residues; and

iii) 0 to 10 mole % of aromatic dicarboxylic acid residues having up to 20 carbon atoms; and

(B) a glycol component comprising;

i) 5 to 35 mole % of 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues; and

ii) 65 to 95 mole % of cyclohexanedimethanol residues;

wherein the total mole % of said dicarboxylic acid component is equal to 100 mole %;

the total mole % of said glycol component is equal to 100 mole %;

wherein the inherent viscosity of said polyester is from 0.35 to 1.2 dL/g as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25°

C.; and

wherein said polyester has a Tg of from 66 to 120°

C.

2. The polyester composition of claim 1, wherein the inherent viscosity of said polyester is from 0.5 to 1.2 dL/g.

3. The polyester composition of claim 1, wherein the inherent viscosity of said polyester is from 0.35 to 1.0 dL/g.

4. The polyester composition of claim 1, wherein the inherent viscosity of said polyester is from 0.35 to 0.75 dL/g.

5. The polyester composition of claim 1, wherein the inherent viscosity of said polyester is from 0.40 to 0.90 dL/g.

6. The polyester composition of claim 1, wherein the inherent viscosity of said polyester is from greater than 0.42 to 0.80 dL/g.

7. The polyester composition of claim 1, wherein the inherent viscosity of said polyester is from 0.5 to 0.8 dL/g.

8. The polyester composition of claim 1, wherein the inherent viscosity of said polyester is from 0.6 to 0.8 dL/g.

9. The polyester composition of claim 1, wherein the inherent viscosity of said polyester is from 0.60 to 0.72 dL/g.

10. The polyester composition of claim 1, wherein the inherent viscosity of said polyester is from 0.65 to 0.75 dL/g.

11. The polyester composition of claim 1, wherein the inherent viscosity of said polyester is from 0.75 to 0.85 dL/g.

12. The polyester composition of claim 1, wherein the inherent viscosity of said polyester is from 0.74 to 0.8 dL/g.

13. The polyester composition of claim 1, wherein the inherent viscosity of said polyester is from greater than 0.70 up to 0.85 dL/g.

14. The polyester composition of claim 1, wherein the inherent viscosity of said polyester is from 0.72 to 0.85 dL/g.

15. The polyester composition of claim 1, wherein said polyester has a Tg of 66 to 110°

C.

16. The polyester composition of claim 1, wherein said polyester has a Tg of 66 to 100°

C.

17. The polyester composition of claim 1, wherein said polyester has a Tg of 66 to 90°

C.

18. The polyester composition of claim 1, wherein said polyester has a Tg of 70 to 90°

C.

19. The polyester composition of claim 1, wherein the dicarboxylic acid component comprises 0.01 to 10 mole % of aromatic dicarboxylic acid residues.

20. The polyester composition of claim 1, wherein the dicarboxylic acid component comprises 0.05 to 10 mole % of aromatic dicarboxylic acid residues.

21. The polyester composition of claim 1, wherein the dicarboxylic acid component comprises 0.1 to 10 mole % of aromatic dicarboxylic acid residues.

22. The polyester composition of claim 1, wherein the dicarboxylic acid component comprises 0.01 to 5 mole % of aromatic dicarboxylic acid residues.

23. The polyester composition of claim 1, wherein the dicarboxylic acid component comprises 0.1 to 5 mole % of aromatic dicarboxylic acid residues.

24. The polyester composition of claim 1, wherein the dicarboxylic acid component comprises 1 to 5 mole % of aromatic dicarboxylic acid residues.

25. The polyester composition of claim 1, wherein the dicarboxylic acid component comprises aromatic dicarboxylic acids chosen from terephthalic acid residues, isophthalic acid residues, naphthalenedicarboxylic acid residues, or esters thereof or mixtures thereof.

26. The polyester composition of claim 1, wherein the dicarboxylic acid component comprises aliphatic dicarboxylic acids chosen from at least one of malonic acid residues, succinic acid residues, glutaric acid residues, adipic acid residues, suberic acid residues, azelaic acid residues, sebacic acid residues or esters thereof or mixtures thereof.

27. The polyester composition of claim 1, wherein the dicarboxylic acid component comprises aliphatic dicarboxylic acids chosen from at least one of adipic acid residues, succinic acid residues, or esters thereof or mixtures thereof.

28. The polyester composition claim 1 wherein said polyester comprises ethylene glycol, 1,3-propanediol residues, 1,4-butanediol residues, or mixtures thereof.

29. The polyester composition claim 1 wherein said polyester comprises ethylene glycol.

30. The polyester composition of claim 1, wherein said cyclohexanedicarboxylic acid residues are a mixture comprising 80 to 98 mole % of trans-cyclohexanedicarboxylic acid and 2 to 20 mole % of cis-cyclohexanedicarboxylic acid.

31. The polyester composition of claim 1, wherein said cyclohexanedicarboxylic acid residues are a mixture comprising 90 to 98 mole % of trans-cyclohexanedicarboxylic acid and 2 to 10 mole % of cis-cyclohexanedicarboxylic acid.

32. The polyester composition of claim 1, wherein said cyclohexanedicarboxylic acid residues are a mixture comprising 92 to 98 mole % of trans-cyclohexanedicarboxylic acid and 2 to 8 mole % of cis-cyclohexanedicarboxylic acid.

33. The polyester composition of claim 1, wherein said cyclohexanedicarboxylic acid residues is a mixture comprising 95 to 98 mole % of trans-cyclohexanedicarboxylic acid and 2 to 5 mole % of cis-cyclohexanedicarboxylic acid.

34. The polyester composition of claim 1, wherein said cyclohexanedicarboxylic acid residues are a mixture comprising 78 to 87 mole % of trans-cyclohexanedicarboxylic acid and 13 to 22 mole % of cis-cyclohexanedicarboxylic acid.

35. The polyester composition of any of claims 30-34 wherein said cyclohexanedicarboxylic acid residues are derived from 1,4-cyclohexanedicarboxylic acid or esters thereof.

36. The polyester composition of claim 1, wherein said polyester composition 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;

poly(ester-carbonates);

polycarbonates;

polysulfones;

polysulfone ethers; and

poly(ether-ketones) of aromatic dihydroxy compounds;

or mixtures thereof.

37. The polyester composition of claim 1, wherein said polyester composition comprises at least one polycarbonate.

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

39. The polyester composition of claim 1, wherein said polyester comprises at least one branching agent residue in an amount of 0.01 to 5 weight % based on the total weight of the polyester.

40. The polyester composition of claim 1, wherein said polyester has a crystallization half-time of greater than 5 minutes at 170°

C.

41. The polyester composition of claim 1, wherein said polyester composition has a density of 1.05 to 1.2 g/ml at 23°

C.

42. The polyester composition of claim 1, wherein said polyester composition comprises at least one phosphorus compound.

43. The polyester composition of claim 1, wherein said polyester composition comprises at least one tin compound.

44. The polyester composition of claim 1, wherein said polyester compositions comprises at least one titanium compound and one tin compound.

45. The polyester composition of claim 1, wherein said polyester has a notched Izod impact strength of at least 5 ft-lbs/in at 23°

C. according to ASTM D256 with a 10-mil notch in a ⅛

-inch thick bar.

46. An article of manufacture comprising the polyester composition of claim 1, comprising a film or sheet.

47. An article of manufacture comprising the polyester composition of claim 1, comprising multi-sheets.

48. The polyester composition of claim 46 wherein said film or sheet is incorporated into at least one of the following:

building and construction materials, auto panels, and optical media.

52. The polyester composition of any of claims 1 and 51, wherein said polyester has a Tg of 66 to 90°

C.

55. A thermoplastic article comprising:

a first layer comprising a polymeric material; and

a protective layer comprising at least one of the polyesters of any of claims 1, 49-52;

optionally, at least one antioxidant as described herein, and

optionally, at least one ultraviolet light absorbing compound.

49. A polyester composition comprising at least one polyester which comprises:

(A) a dicarboxylic acid component comprising;

i) 70 to 100 mole % of cyclohexanedicarboxylic acid residues or an ester thereof comprising;

(a) 80 to 99 mole % trans-cyclohexanedicarboxylic acid residues or an ester thereof and

(b) 1 to 20 mole % cis-cyclohexanedicarboxylic acid residues or an ester thereof;

ii) 0 to 30 mole % of aliphatic dicarboxylic acid residues, other than cyclohexanedicarboxylic acid residues, having up to 16 carbon atoms or esters thereof, other than cyclohexanedicarboxylic acid residues, or esters thereof; and

iii) 0 to 10 mole % of aromatic dicarboxylic acid residues having up to 20 carbon atoms; and

(B) a glycol component comprising;

i) 15 to 35 mole % of 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues; and

ii) 65 to 85 mole % of 1,4-cyclohexanedimethanol residues, 1,3-cyclohexanedimethanol residues, 1,2-cyclohexanedimethanol residues or esters thereof or mixtures thereof,

wherein the total mole % of said dicarboxylic acid component is equal to 100 mole %;

the total mole % of said glycol component is equal to 100 mole %;

wherein the inherent viscosity of said polyester is from 0.5 to 1.2 dL/g as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25°

C.; and

wherein said polyester has a Tg of from 66 to 120°

C.

50. A polyester composition comprising at least one polyester which comprises:

(A) a dicarboxylic acid component comprising;

i) 70 to 100 mole % of cyclohexanedicarboxylic acid residues or an ester thereof comprising;

(a) 80 to 98 mole % trans-cyclohexanedicarboxylic acid residues or an ester thereof and

(b) 2 to 20 mole % cis-cyclohexanedicarboxylic acid residues or an ester thereof;

ii) 0 to 30 mole % of aliphatic dicarboxylic acid residues, other than cyclohexanedicarboxylic acid residues, having up to 16 carbon atoms or esters thereof, other than cyclohexanedicarboxylic acid residues, or esters thereof; and

iii) 0 to 10 mole % of aromatic dicarboxylic acid residues having up to 20 carbon atoms; and

(B) a glycol component comprising;

i) 5 to 35 mole % of 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues; and

ii) 65 to 95 mole % of 1,4-cyclohexanedimethanol residues, 1,3-cyclohexanedimethanol residues, 1,2-cyclohexanedimethanol residues or esters thereof or mixtures thereof,

wherein the total mole % of said dicarboxylic acid component is equal to 100 mole %;

the total mole % of said glycol component is equal to 100 mole %;

wherein the inherent viscosity of said polyester is from 0.5 to 1.2 dL/g as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25°

C.; and

wherein said polyester has a Tg of from 66 to 120°

C.

53. The polyester composition of any of claims 50 and 51, wherein said polyester has an inherent viscosity of 0.72 to 0.85 dL/g as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25°

C.

54. The polyester composition of any of claims 50 and 51, wherein said polyester has an inherent viscosity of 0.75 to 0.85 dL/g as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25°

C.

51. A polyester composition comprising at least one polyester which comprises:

(A) a dicarboxylic acid component comprising;

i) 70 to 100 mole % of cyclohexanedicarboxylic acid residues or an ester thereof comprising;

(a) 80 to 98 mole % trans-cyclohexanedicarboxylic acid residues or an ester thereof and

(b) 2 to 20 mole % cis-cyclohexanedicarboxylic acid residues or an ester thereof;

ii) 0 to 30 mole % of aliphatic dicarboxylic acid residues, other than cyclohexanedicarboxylic acid residues, having up to 16 carbon atoms esters thereof, other than cyclohexanedicarboxylic acid residues, or esters thereof; and

iii) 0 to 10 mole % of aromatic dicarboxylic acid residues having up to 20 carbon atoms; and

(B) a glycol component comprising;

i) 25 to 35 mole % of 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues; and

ii) 65 to 75 mole % of 1,4-cyclohexanedimethanol residues, 1,3-cyclohexanedimethanol residues, 1,2-cyclohexanedimethanol residues or esters thereof or mixtures thereof,

wherein the total mole % of said dicarboxylic acid component is equal to 100 mole %;

the total mole % of said glycol component is equal to 100 mole %;

wherein the inherent viscosity of said polyester is from 0.5 to 1.2 dL/g as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25°

C.; and

wherein said polyester has a Tg of from 80 to 120°

C.