IP Library Granted Patent US 9,018,284
Granted Patent B2
US 9,018,284 · App. 13/102,597 · Granted Apr 28, 2015

Oxygen scavenging additives for plastic containers

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Quick Facts
Patent No.
US 9,018,284
App. No.
13/102,597
Granted
Apr 28, 2015
Kind
B2
Abstract

The present invention provides a composition comprising: a base polymer; at least one compound having the structure of Formula I or II wherein Ar is an o-, m-, or p-phenylene moiety, a substituted phenylene moiety, or a naphthalene moiety; R 1 and R 2 are independently selected from the group consisting of: hydrogen, alkyl, alkenyl, and aryl; and X is O or —(CH 2 ) n —; n=0, 1, or 2; and p=0, 1, or 2; and; and at least one transition metal in a positive oxidation state, said metal being present in the composition in an amount of from about 10 to about 400 ppm, wherein said compound is present in an amount of from about 0.10 to about 10 weight percent of the composition.

Claims (54)

1. A composition comprising:

a) a base polymer;

b) at least one non-polymeric oxidizable organic compound having the structure of Formula I or II:

wherein:

Ar is an o-, m-, or p-phenylene moiety, a substituted phenylene moiety, or a naphthalene moiety;

R 1 and R 2 are independently selected from the group consisting of: hydrogen, alkyl, alkenyl, and aryl;

X is O or —(CH 2 ) n —; and

n=0, 1, or 2;

p=0, 1, or 2; and

c) at least one transition metal in a positive oxidation state, said metal being present in the composition in an amount of from about 10 to about 400 ppm,

wherein said compound is present in an amount of from about 0.10 to about 10 weight percent of the composition.

2. The composition of claim 1 , wherein said at least one transition metal is cobalt.

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

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

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

6. 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.

7. The composition 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 composition 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 composition of claim 1 wherein the concentration of transition metal is 30 to 150 ppm.

10. The composition of claim 1 wherein the non-polymeric oxidizable organic compound is m-xylylene-bis-(tetrahydrophthalimide):

11. The composition of claim 1 wherein the non-polymeric oxidizable organic compound is m-xylylene-bis-citraconimide:

12. A composition comprising:

a) polyethylene terephthalate;

b) m-xylylene-bis-(tetrahydrophthalimide):

c) at least one transition metal in a positive oxidation state, said metal being present in the composition in an amount of from about 10 to about 400 ppm,

wherein the m-xylylene-bis-(tetrahydrophthalimide) is present in an amount of from about 0.10 to about 10 weight percent of the composition.

13. The composition of claim 12 , wherein said at least one transition metal is cobalt.

14. The composition of claim 13 wherein the concentration of transition metal is 30 to 150 ppm.

15. A wall for a package comprising at least one layer, said layer comprising a composition, said composition comprising:

a) a base polymer;

b) at least one compound having the structure of Formula I or II

wherein:

Ar is an o-, m-, or p-phenylene moiety, a substituted phenylene moiety, or a naphthalene moiety;

R 1 and R 2 are independently selected from the group consisting of: hydrogen, alkyl, alkenyl, and aryl; and

X is O or —(CH 2 ) n —; and

n=0, 1, or 2;

p=0, 1, or 2; and

c) at least one transition metal in a positive oxidation state, said metal being present in the composition in an amount of from about 10 to about 400 ppm,

wherein said compound is present in an amount of from about 0.10 to about 10 weight percent of the composition.

16. The wall of claim 15 , wherein said at least one transition metal is cobalt.

17. The wall of claim 16 wherein said at least one transition metal further comprises zinc.

18. The wall of claim 15 wherein said base polymer comprises a polyester polymer.

19. The wall of claim 18 wherein the polyester polymer is polyethylene terephthalate.

20. The wall of claim 15 wherein the compound is present in an amount of about 1 to about 10 weight percent based on the weight of the composition.

21. The wall of claim 15 wherein the compound is present in an amount of about 1 to about 5 weight percent based on the weight of the composition.

22. The wall of claim 15 wherein the compound is present in an amount of about 1 to about 3 weight percent based on the weight of the composition.

23. The wall of claim 15 wherein the concentration of transition metal is 30 to 150 ppm.

24. A wall for a package comprising at least one layer, said layer comprising a composition, said composition comprising:

a) polyethylene terephthalate;

b) m-xylylene-bis-(tetrahydrophthalimide):

c) at least one transition metal in a positive oxidation state, said metal being present in the composition in an amount of from about 10 to about 400 ppm,

wherein the m-xylylene-bis-(tetrahydrophthalimide) is present in an amount of from about 0.10 to about 10 weight percent of the composition.

25. The wall of claim 24 , wherein said at least one transition metal is cobalt.

26. The wall of claim 25 wherein the concentration of transition metal is 30 to 150 ppm.

Assignments (7)
RELEASE OF SECURITY INTEREST Recorded Jan 26, 2026
From: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
To: GRAHAM PACKAGING COMPANY, L.P.; GRAHAM PACKAGING PET TECHNOLOGIES INC.; GRAHAM PACKAGING PLASTIC PRODUCTS LLC
Reel/Frame 074480/0105 →
SECURITY INTEREST Recorded Aug 4, 2020
From: GRAHAM PACKAGING COMPANY, L.P.; GRAHAM PACKAGING PET TECHNOLOGIES INC.; GRAHAM PACKAGING PLASTIC PRODUCTS LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 053398/0381 →
RELEASE OF SECURITY INTEREST IN CERTAIN PATENT COLLATERAL Recorded Aug 4, 2020
From: THE BANK OF NEW YORK MELLON, AS THE COLLATERAL AGENT AND TRUSTEE
To: GRAHAM PACKAGING COMPANY, L.P.
Reel/Frame 053396/0531 →
PATENT SECURITY AGREEMENT Recorded Mar 22, 2012
From: GRAHAM PACKAGING COMPANY, L.P.
To: THE BANK OF NEW YORK MELLON
Reel/Frame 027910/0609 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 20, 2012
From: REYNOLDS GROUP HOLDINGS INC.
To: GRAHAM PACKAGING COMPANY, L.P.
Reel/Frame 027895/0738 →
SECURITY AGREEMENT Recorded Sep 26, 2011
From: GRAHAM PACKAGING COMPANY, L.P.
To: REYNOLDS GROUP HOLDINGS INC.
Reel/Frame 026970/0699 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 19, 2011
From: AKKAPEDDI, MURALI K.; LYNCH, BRIAN A.
To: GRAHAM PACKAGING COMPANY, L.P.
Reel/Frame 026614/0977 →