Oxygen scavenging molecules, articles containing same, and methods of their use

Patent metadata

Field	Value
Publication number	US-10125096-B2
Application number	US-201615147532-A
Country	US
Kind code	B2
Filing date	May 5, 2016
Priority date	May 10, 2007
Publication date	Nov 13, 2018
Grant date	Nov 13, 2018

Abstract

The invention relates to compounds of the structure of formula I and II:

where X is selected from the group consisting of O, S and NH; Y, A and B are independently selected from the group consisting of N and CH; D, E and F are independently selected from the group consisting of CH, N, O and S; the symbol - - - - represents a single or a double bond; and R 1 , R 2 and R 3 are independently selected from the group consisting of H, electron withdrawing groups and electron releasing groups. In other embodiments, the compounds are used as oxygen scavengers and in barrier compositions and articles.

First claim

What is claimed:

1. A wall for a package comprising a composition, said wall comprising:
(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 a composition comprising:
(1) a base polymer;
(2) at least one compound of Formula I or II

wherein X is selected from the group consisting of O, S and NH;
Y, A and B are independently selected from the group consisting of N and CH;
D, E and F are independently selected from the group consisting of CH, N, O and S;
the symbol - represents a single or a double bond; and
R 1 , R 2 and R 3 are independently selected from the group consisting of H, electron withdrawing groups and electron releasing groups and a transition metal; and
(3) at least one transition metal in a positive oxidation state, said metal being present in the composition in an amount of 10 to 400 ppm; wherein said compound is present in an amount of about 0.10 to 10 weight percent of said composition.

2. The wall of claim 1 said at least one transition metal comprises cobalt.

3. The wall of claim 2 wherein said at least one transition metal further comprises zinc.

4. The wall of claim 1 wherein said base polymer comprises a polyester polymer.

5. The wall of claim 4 wherein the polyester polymer is polyethylene terephthalate.

6. The wall 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.

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

8. The wall of claim 1 wherein the compound is present in an amount of about 1 to about 3 weight percent based on the weight of the composition.

9. The wall of claim 1 wherein said first layer is disposed radially outward from said second layer.

10. The wall of claim 1 , wherein the compound is

11. The wall of claim 1 , wherein the compound is

12. A method for producing a packaging material having a wall with oxygen barrier properties comprising:
(a) combining a base polymer with at least one compound of Formula I or II

wherein X is selected from the group consisting of O, S and NH;
Y, A and B are independently selected from the group consisting of N and CH;
D, E and F are independently selected from the group consisting of CH, N, O and S;
the symbol - represents a single or a double bond; and
R 1 , R 2 and R 3 are independently selected from the group consisting of H, electron withdrawing groups and electron releasing groups and a transition metal;
to form a composition, the composition having at least one transition metal in a positive oxidation state, said metal being present in the composition in an amount of 10 to 400 ppm; and
wherein said compound is present in an amount of about 0.10 to 10 weight present of said composition;
(b) forming the product of step (a) into a wall; and
(c) forming a container which comprises said wall.

13. The method of claim 12 wherein said at least one transition metal comprises cobalt.

14. The method of claim 13 said at least one transition metal further zinc.

15. The method of claim 12 wherein said base polymer comprises a polyester polymer.

16. The method of claim 15 wherein the polyester polymer is polyethylene terephthalate.

17. The method of claim 12 wherein the compound is present in an amount of about 1 to about 10 weight percent based on the weight of the composition.

18. The method of claim 12 wherein the compound is present in an amount of about 1 to about 5 weight percent based on the weight of the composition.

19. The method of claim 12 wherein the compound is present in an amount of about 1 to about 3 weight percent based on the weight of the composition.

20. The method of claim 12 wherein the concentration of transition metal is 30 to 150 ppm.

21. The method of claim 12 , wherein the compound is

22. The method of claim 12 , wherein the compound is

Assignees

• Plastipak Packaging Inc

Inventors

• Deshpande Girish Nilkanth
• Weipert Paul David
• Ensley Michael W

Classifications

• C07D207/00 Primary

  Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom · CPC title

• C08K5/0091

  Complexes with metal-heteroatom-bonds · CPC title

• C07D209/48

  with oxygen atoms in positions 1 and 3, e.g. phthalimide · CPC title

• B01J20/262

  obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation (macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds per se C08G) · CPC title

• C07D209/46

  with an oxygen atom in position 1 · CPC title