Polyether ester elastomer comprising polytrimethylene ether ester soft segment and trimethylene ester hard segment

• US 6,599,625 B2
• Filed: 10/31/2001
• Issued: 07/29/2003
• Est. Priority Date: 10/31/2001
• Status: Expired due to Term

• Current Assignee: DuPont Industrial Biosciences USA, LLC (DuPont de Nemours, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Goldfinger, Marc B., Sunkara, Hari B.
• Primary Examiner(s): Acquah, Samuel A.
• Application Number:
  US10/016,023
• Publication Number:
  US 20030120026A1
• Time in Patent Office: 636 Days
• Field of Search: 528/176, 528/190, 528/193, 528/194, 528/298, 528/300, 528/301, 528/302, 528/307, 528/308, 528/308.6, 428/359, 428/365, 428/373, 428/375, 264/176
• US Class Current: 428/365
• CPC Class Codes: C08G 63/672 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: Y10T 428/2904 Staple length fiber
• CPC Class Codes: Y10T 428/2915 including textile, cloth or fabric
• CPC Class Codes: Y10T 428/2929 Bicomponent, conjugate, composite or collateral fibers or filaments [i.e., coextruded sheath-core or side-by-side type]
• CPC Class Codes: Y10T 428/2933 Coated or with bond, impregnation or core

Abstract

A polyether ester elastomer comprising about 90-about 60 weight % polytrimethylene ether ester soft segment and about 10-about 40 weight % trimethylene ester hard segment, and use thereof in fibers and other shaped articles. The fibers have excellent physical properties, including superior strength and stretch recovery.

Claims

1. A polyether ester elastomer comprising about 90-about 60 weight % polytrimethylene ether ester soft segment and about 10-about 40 weight % trimethylene ester hard segment.

2. A polyether ester as claimed in claim 1 about 85-about 70 weight % polytrimethylene ether ester soft segment and about 15-about 30 weight % trimethylene ester hard segment.

3. A polyether ester as claimed in claim 1 about 82-about 74 weight % polytrimethylene ether ester soft segment and about 18-about 26 weight % trimethylene ester hard segment.

4. A polyether ester as claimed in claim 1 wherein the mole ratio of hard segment to soft segment is in the range of about 2.0-about 4.5.

5. A polyether ester as claimed in claim 1 wherein the mole ratio of hard segment to soft segment is in the range of about 2.5-about 4.0.

6. A polyether ester as claimed in claim 1 having an inherent viscosity of about 1.4-about 2.4 dl/g.

7. A polyether ester as claimed in claim 1 prepared by providing and reacting (a) polytrimethylene ether glycol, (b) 1,3-propanediol and (c) dicarboxylic acid, ester, acid chloride or acid anhydride.

8. A polyether ester as claimed in claim 7 wherein the polytrimethylene ether ester soft segment is prepared from polymeric ether glycol and the dicarboxylic acid, ester, acid chloride or acid anhydride, greater than 50 weight % of the polymeric ether glycol used to form the polytrimethylene ether ester soft segment is the polytrimethylene ether glycol.

9. A polyether ester as claimed in claim 7 wherein the polytrimethylene ether ester soft segment is prepared from polymeric ether glycol and the dicarboxylic acid, ester, acid chloride or acid anhydride, at least 40 weight % of the polymeric ether glycol used to form the polytrimethylene ether ester soft segment is the polytrimethylene ether glycol, and up to 60 weight % of the polymeric ether glycol used to form the polytrimethylene ether ester soft segment is polymeric ether glycol selected from the group consisting of polyethylene ether glycol, polypropylene ether glycol, polytetramethylene ether glycol, polyhexamethylene ether glycol, and copolymers of tetrahydrofuran and 3-alkyl tetrahydrofuran, and mixtures thereof.

10. A polyether ester as claimed in claim 9 wherein at least 85 weight % of the polymeric ether glycol used to form the polytrimethylene ether ester soft segment is the polytrimethylene ether glycol.

11. A polyether ester as claimed in claim 7 wherein the polytrimethylene ether glycol has number average molecular weight of at least about 1,000.

12. A polyether ester as claimed in claim 7 wherein the polytrimethylene ether glycol has number average molecular weight of about 1,000-about 5,000.

13. A polyether ester as claimed in claim 7 wherein the polytrimethylene ether glycol has number average molecular weight of less than about 5,000.

14. A polyether ester as claimed in claim 7 wherein the polytrimethylene ether glycol has a number average molecular weight in the range of about 1,500 to about 3,500.

15. A polyether ester as claimed in claim 7 wherein the trimethylene ester hard segment is prepared from diol and the dicarboxylic acid, ester, acid chloride or acid anhydride, at least 75 mole % of the diol used to form the trimethylene ester hard segment is 1,3-propanediol and up to 25 mole % of the diol is diol other than 1,3-propanediol with 2-15 carbon atoms.

16. A polyether ester as claimed in claim 15 wherein the diol other than 1,3-propanediol are selected from ethylene, isobutylene, tetramethylene, pentamethylene, 2,2-dimethyltrimethylene, 2-methyltrimethylene, hexamethylene and decamethylene glycols, dihydroxy cyclohexane, cyclohexane dimethanol, hydroquinone bis(2-hydroxyethyl) ether, and mixtures thereof.

17. A polyether ester as claimed in claim 15 wherein the diol other than 1,3-propanediol contain 2-8 carbon atoms.

18. A polyether ester as claimed in claim 15 wherein the diol other than 1,3-propanediol are selected from the group consisting of ethylene glycol and 1,4-butanediol, and mixtures thereof.

19. A polyether ester as claimed in claim 15 wherein at least 85 mole % of the diol used to form the trimethylene ester hard segment is 1,3-propanediol.

20. A polyether ester as claimed in claim 7 wherein the dicarboxylic acid, ester, acid chloride or acid anhydride is an aromatic dicarboxylic acid or diester.

21. A polyether ester as claimed in claim 7 wherein the dicarboxylic acid, ester, acid chloride or acid anhydride is selected from the group consisting of dimethyl terephthalate, bibenzoate, isophthlate, phthalate and naphthalate;

terephthalic, bibenzoic, isophthalic, phthalic and naphthalic acid, and mixtures thereof.

22. A polyether ester as claimed in claim 7 wherein at least 50 mole % the dicarboxylic acid, ester, acid chloride or acid anhydride is selected from the group consisting of terephthalic acid and dimethyl terephthalate.

23. A polyether ester as claimed in claim 7 wherein the dicarboxylic acid, ester, acid chloride or acid anhydride is selected from the group consisting of terephthalic acid and dimethyl terephthalate.

24. A polyether ester as claimed in claim 7 having an inherent viscosity of about 1.4-about 2.4 dl/g, wherein the mole ratio of hard segment to soft segment is in the range of about 2.0-about 4.5;

the polytrimethylene ether ester soft segment is prepared from polymeric ether glycol and the dicarboxylic acid, ester, acid chloride or acid anhydride;

at least 40 weight % of the polymeric ether glycol used to form the polytrimethylene ether ester soft segment is the polytrimethylene ether glycol having a number average molecular weight of about 1,000-about 5,000, up to 60 weight % of the polymeric ether glycol used to form the polytrimethylene ether ester soft segment is polymeric ether glycol selected from the group consisting of polyethylene ether glycol, polypropylene ether glycol, polytetramethylene ether glycol, polyhexamethylene ether glycol, and copolymers of tetrahydrofuran and 3-alkyl tetrahydrofuran, and mixtures thereof;

the trimethylene ester hard segment is prepared from diol and the dicarboxylic acid, ester, acid chloride or acid anhydride;

at least 75 mole % of the diol used to form the trimethylene ester hard segment is 1,3-propanediol and up to 25 mole % of the diol are diol selected from ethylene, isobutylene, tetramethylene, pentamethylene, 2,2-dimethyltrimethylene, 2-methyltrimethylene, hexamethylene and decamethylene glycols, dihydroxy cyclohexane, cyclohexane dimethanol, hydroquinone bis(2-hydroxyethyl) ether, and mixtures thereof; and

the dicarboxylic acid, ester, acid chloride or acid anhydride is selected from the group consisting of dimethyl terephthalate, bibenzoate, isophthlate, phthalate and naphthalate, terephthalic, bibenzoic, isophthalic, phthalic and naphthalic acid, and mixtures thereof.

25. A polyether ester as claimed in claim 7 having an inherent viscosity of about 1.4-about 2.4 dl/g, wherein the mole ratio of hard segment to soft segment is in the range of about 2.5-about 4.0, at least 85 weight % of the polymeric ether glycol used to form the polytrimethylene ether ester soft segment is the polytrimethylene ether glycol;

at least 85 mole % of the diol used to form the trimethylene ester hard segment is the 1,3-propanediol;

the polytrimethylene ether glycol has a number average molecular weight in the range of about 1,500 to about 3,500;

at least 70 mole % the dicarboxylic acid, ester, acid chloride or acid anhydride is selected from the group consisting of terephthalic acid and dimethyl terephthalate.

26. A polyether ester as claimed in claim 1 prepared by providing and reacting polytrimethylene ether glycol and polytrimethylene ester.

28. A polyether ester as claimed in claim 1 in the form of a fiber.

29. A polyether ester as claimed in claim 28 wherein the fiber is a monocomponent filament.

30. A polyether ester as claimed in claim 28 wherein the fiber is a staple fiber.

31. A polyether ester as claimed in claim 1 wherein the polyether ester in the form of a component of a multicomponent fiber.

32. A woven or knit fabric comprising fibers comprising the polyether ester of claim 1.

33. A nonwoven fabric comprising fibers comprising the polyether ester of claim 1.

34. A process of preparing a polyether ester as claimed in claim 1 by providing and reacting (a) polytrimethylene ether glycol, (b) 1,3-propanediol and (c) dicarboxylic acid, ester, acid chloride or acid anhydride.

35. A process of preparing a polyether ester as claimed in claim 1 by providing and reacting polytrimethylene ether glycol and trimethylene ester.

36. A process of preparing a polyether ester as claimed in claim 1 prepared by providing and reacting polytrimethylene ether glycol and polytrimethylene ester.

37. A process of preparing a fiber by providing the polyether ester of claim 1 and spinning the polyether ester to form a fiber.

38. A process of preparing a fabric comprising (a) providing fibers, the fibers comprising fibers comprising the polyether ester of claim 1 and (b) forming a fabric from the fibers.

27. A polyether ester comprising a soft segment represented by the structure:

and a hard segment represented by the structure;

where x is about 17 to about 86 and R and R′

, which may be the same or different, are divalent radicals remaining after removal of carboxyl functionalities from dicarboxylic acid equivalent.