Oxygen scavengers, compositions comprising the scavengers, and articles made from the compositions
View Patent ↗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.
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.