Oxygen scavengers, compositions comprising the scavengers, and articles made from the compositions

Patent metadata

Field	Value
Publication number	US-10351692-B2
Application number	US-201414517643-A
Country	US
Kind code	B2
Filing date	Oct 17, 2014
Priority date	Oct 17, 2014
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

Abstract

The disclosure relates to oxygen scavenging molecules, compositions, methods of making the compositions, articles prepared from the compositions, and methods of making the articles. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

First claim

What is claimed is:

1. A composition comprising:
a. a base polymer;
b. at least one compound of the following formula:

wherein Ar is aryl
wherein each occurrence of R 1 is independently selected from hydrogen, halogen, C1-C4 alkyl,

 electron withdrawing groups, and electron donating groups;
wherein Ar 2 is independently aryl or heteroaryl; and wherein Ar 2 is independently substituted with 0, 1, 2, or 3 groups independently selected from halogen, C1-C4 alkyl, electron withdrawing groups and electron donating groups, and valence is satisfied;
wherein R 10 is independently selected from hydrogen, C1-C4 alkyl, —C(O)R 20 , and —C(O)Ar 3 ;
wherein R 20 is C1-C4 alkyl;
wherein each Ar 3 is phenyl or naphthyl; and wherein each Ar 3 is independently substituted with 0, 1, 2, or 3 groups independently selected from halogen, C1-C4 alkyl, —CO 2 R 30 ; electron withdrawing group and electron donating groups, and valence is satisfied;
wherein R 30 , when present, is selected from hydrogen, C1-C4 alkyl, —(CH 2 ) n OH, and —CH 2 Ar 4 ;
wherein n is an integer selected from 1 or 2;
wherein Ar 4 , when present, is aryl substituted with 0, 1, 2, and 3 groups selected from halogen, C1-C4 alkyl, and —C(O)NHCH 2 Ar 5 ;
wherein each Ar 5 , when present, is aryl substituted with 0, 1, 2, or 3 groups independently selected from halogen, C1-C4 alkyl,

 electron withdrawing groups, and electron donating groups;
wherein each R 40 , when present, is independently selected from hydrogen, C1-C4 alkyl, electron withdrawing groups, and electron donating groups;
wherein each Ar 6 , when present, is aryl substituted with 0, 1, 2, and 3 groups independently selected from hydrogen, C1-C4 alkyl, electron withdrawing groups, and electron donating groups;
wherein R 2 is independently selected from hydrogen, C1-C4 alkyl, —C(O)R 50 , and —C(O)Ar 7 ;
wherein R 50 is C1-C4 alkyl;
wherein each Ar 7 is aryl substituted with 0, 1, 2, and 3 groups independently selected from hydrogen, C1-C4 alkyl, and electron withdrawing groups, and electron donating groups, and valence is satisfied; and

c. at least one transition metal in a positive oxidation state.

2. The composition of claim 1 , wherein the at least one transition metal is present in the composition in an amount of 10 to 400 ppm.

3. The composition of claim 1 , wherein the at least one transition metal is cobalt or zinc, or a combination thereof.

4. The composition of claim 1 , wherein the base polymer comprises a polyester polymer.

5. The composition of claim 1 , wherein the compound is present in an amount of about 1 to about 10 weight percent based on the weight of the composition.

6. The composition of claim 1 , wherein the compound has the structure

7. An article of manufacture comprising the composition of claim 1 .

8. A wall of a package comprising at least one layer, said layer comprising a composition according to claim 1 .

9. The wall of claim 8 , wherein said wall comprises
a. one or more outer layers; and
b. one or more inner layers;
wherein at least one of said inner or at least one of said outer layers comprises the composition according to claim 1 .

10. The composition of claim 1 , wherein R 2 is hydrogen.

11. The composition of claim 1 , wherein the compound has the structure

12. The composition of claim 11 , wherein each occurrence of R 1 is hydrogen.

13. The composition of claim 1 , wherein the compound has the structure

14. The composition of claim 1 , wherein the compound has the structure

15. A polymer comprising at least one residue having the following formula:

wherein each of the at least one residue is covalently bonded as a repeating unit in the polymer chain, covalently bonded as a side-chain pendant group, or covalently bonded as an end group of the polymer;
wherein n is 2, 3, 4, 5, or 6;
wherein Ar is aryl and
wherein each occurrence of R 1 , when present, is independently selected from hydrogen, halogen, C1-C4 alkyl, electron withdrawing groups, and electron donating groups.

16. The polymer of claim 15 , wherein the at least one residue comprises:

17. A composition comprising the polymer of claim 15 .

18. The composition of claim 17 , further comprising a base polymer.

19. The composition of claim 18 , wherein the base polymer is a polyester polymer.

20. The composition of claim 18 , further comprising a transition metal in a positive oxidation state, the metal present in an amount of from about 10 ppm to about 400 ppm.

21. The composition of claim 20 , wherein the transition metal is cobalt or zinc, or a combination thereof.

22. An article of manufacture comprising the composition of claim 20 .

23. A container formed from a film-forming polymer, having at least one wall comprising an effective amount of an oxygen-scavenging composition comprising a polymer of claim 15 .

24. An oxygen scavenging composition that reacts with oxygen in the presence of transition metals and salts thereof comprising an effective amount of a polymer according to claim 15 .

25. An oxygen scavenging system comprising:
a. an oxygen scavenging composition comprising a polymer according to claim 15 ;
b. an effective amount of a transition metal catalyst; and
c. a functional barrier permeable to oxygen.

26. The polymer of claim 15 , wherein n is 2 or 3.

27. The polymer of claim 15 , wherein each occurrence of R 1 , when present, is hydrogen.

Assignees

• Plastipak Packaging Inc

Inventors

• Li Shenshen
• Dauzvardis Matthew J

Classifications

• C07C233/78

  with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom · CPC title

• C08G63/916

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C08K5/20 Primary

  Carboxylic acid amides · CPC title

• C07C235/42

  having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton · CPC title

• B65D81/24

  Adaptations for preventing deterioration or decay of contents; Applications to the container or packaging material of food preservatives, fungicides, pesticides or animal repellants (with thermal insulation B65D81/38) · CPC title