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

Patent metadata

Field	Value
Publication number	US-10316167-B2
Application number	US-201414491846-A
Country	US
Kind code	B2
Filing date	Sep 19, 2014
Priority date	Sep 19, 2014
Publication date	Jun 11, 2019
Grant date	Jun 11, 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 formula

wherein Ar is aryl or heteroaryl;
wherein each Q 1 is independently N or P;
wherein each of Ar 1 and Ar 2 is independently aryl or heteroaryl; and wherein each Ar 1 and Ar 2 is independently substituted with 0, 1, 2, or 3 groups independently selected from halogen, C1-C4 alkyl, and electron withdrawing groups, and valence is satisfied;
wherein each of R 1 and R 2 is independently selected from hydrogen,

wherein R 3 represents three groups, each group independently selected from hydrogen, halogen, C1-C4 alkyl, and electron withdrawing groups;
wherein R 4 represents three groups, each group independently selected from hydrogen, halogen, C1-C4 alkyl, and electron withdrawing groups;
wherein R 5 represents four groups, each group independently selected from hydrogen, halogen, C1-C4 alkyl, and electron withdrawing groups;
wherein R 10 represents five groups independently selected from hydrogen, halogen, C1-C4 alkyl, and electron withdrawing groups;
wherein R 11 represents five groups independently selected from hydrogen, halogen, C1-C4 alkyl, and electron withdrawing groups;
wherein R 12 represents three groups independently selected from hydrogen, halogen, C1-C4 alkyl, and electron withdrawing groups;
wherein R 13 represents three groups independently selected from hydrogen, halogen, C1-C4 alkyl, and electron withdrawing groups;
wherein R 14 represents four groups independently selected from hydrogen, halogen, C1-C4 alkyl, and electron withdrawing groups; and
wherein each Q 2 is independently N or P; and

c. cobalt in a positive oxidation state;
wherein said compound is present in an amount of about 0.10 to 10 weight percent of said composition, and
wherein cobalt is present as a salt having an anion selected from chloride, acetate, oleate, stearate, palmitate, 2-ethylhexanoate, neodecanoate, octanoate, lactate, naphthalate, malate, acetylacetonate, linoleate, and ethylene glycolate.

2. The composition of claim 1 , wherein Ar is aryl selected from

wherein each R 26a , R 26b , and R 26c is independently selected from hydrogen, halogen, C1-C4 alkyl, and electron withdrawing groups.

3. The composition of claim 1 , wherein cobalt is present in the composition in an amount of 10 to 400 ppm.

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

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

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

wherein Ar is aryl or heteroaryl;
wherein each Q 1 is independently N or P;
wherein each of Ar 1 and Ar 2 is independently aryl or heteroaryl; and wherein each Ar 1 and Ar 2 is independently substituted with 0, 1, 2, or 3 groups independently selected from halogen, C1-C4 alkyl, and electron withdrawing groups, and valence is satisfied;
wherein each Z 1 and Z 2 are independently hydrogen, halogen, C1-C4 alkyl, electronic withdrawing group, electronic donating group, or collectively ═O; provided that at least one set of Z 1 and Z 2 are hydrogens;
wherein each of R 1 and R 2 is independently selected from hydrogen,

wherein R 10 represents five groups independently selected from hydrogen, halogen, C1-C4 alkyl, and electron withdrawing groups;
wherein R 11 represents five groups independently selected from hydrogen, halogen, C1-C4 alkyl, and electron withdrawing groups;
wherein R 12 represents three groups independently selected from hydrogen, halogen, C1-C4 alkyl, and electron withdrawing groups;
wherein R 13 represents three groups independently selected from hydrogen, halogen, C1-C4 alkyl, and electron withdrawing groups;
wherein R 14 presents four groups independently selected from hydrogen, halogen, C1-C4 alkyl, and electron withdrawing groups;
wherein each Q 2 is independently N or P;
wherein each Z 3 and Z 4 are independently hydrogen, halogen, C1-C4 alkyl, electronic withdrawing group, electronic donating group, or collectively ═O;
wherein each Z 5 and Z 6 are independently hydrogen, halogen, C1-C4 alkyl, electronic withdrawing group, electronic donating group, or collectively ═O; and
wherein each Z 7 and Z 8 are independently hydrogen, halogen, C1-C4 alkyl, electronic withdrawing group, electronic donating group, or collectively ═O; and

c. cobalt in a positive oxidation state;
wherein said compound is present in an amount of about 0.10 to 10 weight percent of said composition, and
wherein cobalt is present as a salt having an anion selected from chloride, acetate, oleate, stearate, palmitate, 2-ethylhexanoate, neodecanoate, octanoate, lactate, naphthalate, malate, acetylacetonate, linoleate, and ethylene glycolate.

7. An article of manufacture comprising a composition according to claim 1 .

8. The article of claim 7 , wherein the article is a preform, sheet, bottle, cup, or jar.

9. 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 according to claim 1 .

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

11. A container from a film-forming polymer, having at least one wall comprising an effective amount of an oxygen-scavenging composition according to claim 1 .

12. The composition of claim 1 , wherein the compound has the formula:

13. The composition of claim 12 , wherein Ar is aryl, Ar 1 is aryl, Ar 2 is aryl, R 1 is hydrogen, and R 2 is:

14. The composition of claim 1 , wherein cobalt is cobalt (II) 2-ethylhexanoate, cobalt oleate, or cobalt (II) neodecanoate.

15. The composition of claim 6 , wherein cobalt is in the +3 oxidation state.

16. The composition of claim 6 , wherein cobalt is cobalt (II) 2-ethylhexanoate, cobalt oleate, or cobalt (II) neodecanoate.

17. The composition of claim 1 , wherein cobalt is in the +3 oxidation state.

18. A composition comprising:
a. a polyester;
b. at least one compound of formula

c.

Assignees

• Plastipak Packaging Inc
• Plastipak Packaging

Inventors

• Li Shenshen
• Dauzvardis Matthew J

Classifications

• C07D221/06

  Ring systems of three rings · CPC title

• C09K15/30

  containing heterocyclic ring with at least one nitrogen atom as ring member · CPC title

• C07D257/10

  condensed with carbocyclic rings or ring systems · CPC title

• C08K5/17 Primary

  Amines; Quaternary ammonium compounds · CPC title

• C07D209/08

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring · CPC title