ACROLEIN SCAVENGING IN PTF AND OTHER 1,3-PROPANEDIOL DERIVED POLYMERS

• US 20190330420A1
• Filed: 11/03/2017
• Published: 10/31/2019
• Est. Priority Date: 11/03/2016
• Status: Active Grant

• Current Assignee: The Coca-Cola Company
• Original Assignee: The Coca-Cola Company
• Inventors: Kriegel, Robert M., Moffitt, Ronald D., Sukits, Steven F., Nagpal, Jr., Vidhu, Mubarak, Christopher R., Morales, Marlon Salvador
• Granted Patent: US 11,708,454 B2
• Time in Patent Office: Days
• CPC Class Codes: C08G 63/181 Acids containing aromatic rings
• CPC Class Codes: C08G 63/78 Preparation processes
• CPC Class Codes: C08G 63/90 Purification; Drying
• 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: C08K 5/17 Amines; Quaternary ammonium compounds
• CPC Class Codes: C08K 5/20 Carboxylic acid amides
• CPC Class Codes: C08L 101/00 Compositions of unspecified macromolecular compounds
• CPC Class Codes: C08L 67/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C08L67/06 takes precedence

Abstract

This disclosure provides a process for removing acrolein or allyl alcohol from a polyester composition, the process comprising: combining a polyester composition derived from 1,3-propanediol with an amino amide or a primary amine; wherein the amino amide or the primary amine is combined in sufficient quantities to scavenge acrolein or allyl alcohol produced from degradation of the polyester composition. An analysis of reactions between anthranilamide (AAA) and acrolein demonstrates how amines or amino amides can scavenge acrolein from thermally processed poly(trimethylene terephthalate) and poly(trimethylene furan-2,5-dicarboxylate), and thermodynamic models are presented as guidance for matching targets with scavenging agent.

Claims

1. A process for decreasing the acrolein content in a polyester composition, the process comprising:

combining a polyester derived from 1,3-propanediol with an amino amide or a primary amine to form a polyester composition;

wherein the amino amide or the primary amine is combined in an amount sufficient to scavenge acrolein produced from degradation of the polyester composition during melt-processing.

2. The process according to claim 1, wherein combining the polyester composition derived from 1,3-propanediol with the amino amide or the primary amine further comprises combining the amino amide or the primary amine in an amount sufficient to scavenge allyl alcohol produced from degradation of the polyester composition during melt-processing.

3. The process according to claim 1, wherein combining the polyester composition comprises poly(trimethylene furan-2,5-dicarboxylate) (PTF) or poly(trimethylene terephthalate) (PTT).

4. The process according to claim 1, wherein the amino amide or the primary amine is present in the polyester composition in a concentration of from 10 ppm to 10,000 ppm.

5. The process according to claim 1, wherein the amino amide or the primary amine is present in the polyester composition in a concentration of from 100 ppm to about 2,000 ppm.

6. The process according to claim 1, wherein the amino amide comprises a β

-amino amide selected from anthranilamide, 3-aminobutanamide, 3-aminopropanamide, 3-amino-2-methylbutanamide, 3-amino-2-phenylbutanamide, a substituted analog thereof, or any combination thereof.

7. The process according to claim 1, wherein the amide amine comprises an α

-amino amide selected from a 2-aminoacetamide, a 2-aminopropanamide, a 2-alkyl-2-aminoacetamide, a 2-alkyl-2-aminopropanamide, a 2-aryl-2-aminoacetamide, a 2-aryl-2-aminopropanamide, a 2-benzyl-2-aminoacetamide, a 2-benzyl-2-aminopropanamide, a 2-(alkylamino)acetamide, a 2-(alkylamino)propanamide a 2-(arylamino)acetamide, a 2-(arylamino)propanamide, a 2-(benzylamino)acetamide, or a 2-(benzylamino)propanamide, a substituted analog thereof, or any combination thereof.

8. The process according to claim 1, wherein the primary amine is selected from methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, pentylamine, cyclohexyl amine, allyl amine, aniline, or any combination thereof.

9. The process according to claim 1, wherein the amino amide or the primary amine has a thermal decomposition temperature greater than about 250°

C.

10. The process according to claim 1, wherein the combining step is carried out during the synthesis of the polyester composition from 1,3-propanediol and a diacid or a diester.

11. The process according to claim 1, wherein the combining step is carried out during thermal processing of the polyester composition.

12. The process according to claim 1, further comprising the step of fabricating the polyester composition into a film, a fiber, or a container.

13. A polyester composition comprising:

a polyester derived from 1,3-propanediol; and

an amino amide or a primary amine, present in an amount sufficient to scavenge acrolein produced from degradation of the polyester composition during melt-processing.

14. The composition according to claim 13, wherein the amino amide or the primary amine are present in an amount sufficient to further scavenge allyl alcohol produced from degradation of the polyester composition during melt-processing.

15. The composition according to claim 13, wherein the polyester composition comprises poly(trimethylene furan-2,5-dicarboxylate) (PTF) or poly(trimethylene terephthalate) (PTT).

16. The composition according to claim 13, wherein the amino amide or the primary amine is present in the polyester composition in a concentration of from 10 ppm to 10,000 ppm.

17. The composition according to claim 13, wherein the amino amide or the primary amine is present in the polyester composition in a concentration of from 100 ppm to about 2,000 ppm.

18. The composition according to claim 13, wherein the amino amide comprises a β

-amino amide selected from anthranilamide, 3-aminobutanamide, 3-aminopropanamide, 3-amino-2-methylbutanamide, 3-amino-2-phenylbutanamide, a substituted analog thereof, or any combination thereof.

19. The composition according to claim 13, wherein the amide amine comprises an α

-amino amide selected from a 2-aminoacetamide, a 2-aminopropanamide, a 2-alkyl-2-aminoacetamide, a 2-alkyl-2-aminopropanamide, a 2-aryl-2-aminoacetamide, a 2-aryl-2-aminopropanamide, a 2-benzyl-2-aminoacetamide, a 2-benzyl-2-aminopropanamide, a 2-(alkylamino)acetamide, a 2-(alkylamino)propanamide a 2-(arylamino)acetamide, a 2-(arylamino)propanamide, a 2-(benzylamino)acetamide, or a 2-(benzylamino)propanamide, a substituted analog thereof, or any combination thereof.

20. The composition according to claim 13, wherein the primary amine is selected from methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, pentylamine, cyclohexyl amine, allyl amine, aniline, or any combination thereof.

21. The composition according to claim 13, wherein the amino amide or the primary amine has a thermal decomposition temperature greater than about 250°

C.

22. The composition according to claim 13, wherein the combining step is carried out during the synthesis of the polyester composition from 1,3-propanediol and a diacid or a diester.

23. The composition according to claim 13, wherein the combining step is carried out during thermal processing of the polyester composition.

24. A film, a fiber, or a container comprising the polyester composition according to claim 13.