Colorant compatible oxygen scavenging polymer compositions and articles made from same

Patent metadata

Field	Value
Publication number	US-9896554-B2
Application number	US-89381710-A
Country	US
Kind code	B2
Filing date	Sep 29, 2010
Priority date	Sep 29, 2009
Publication date	Feb 20, 2018
Grant date	Feb 20, 2018

Abstract

The disclosure relates to oxygen scavenging polymer 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 melt blended polymer composition comprising:
a. a base polymer;
b. an N-allylic amide compound or N-benzylic amide compound present in an amount of from about 0.10 to about 10 weight percent of the composition;
c. a transition metal in a positive oxidation state, the metal present in an amount of from about 10 ppm to about 400 ppm;
d. a visually effective amount of colorant, and
e. a nonionic colorant harmonizer present in an amount of from about 0.01 to about 10 weight percent of the composition,
wherein at least a portion of the polymer and at least a portion of the amide compound are covalently linked by one or more compatibilizing agents, and wherein when formed into an article the composition has an oxygen transmission rate (OTR) of less than about 0.1 cc/package/day.

2. The composition of claim 1 , wherein the composition has an OTR of less than about 50% of an otherwise identical composition in the absence of the amide compound, the transition metal, and the nonionic colorant harmonizer.

3. The composition of claim 1 , wherein the composition has an OTR of less than about 20% of an otherwise identical composition in the absence of the amide compound, the transition metal, and the nonionic colorant harmonizer.

4. The composition of claim 1 , wherein the composition has an OTR of less than about 10% of an otherwise identical composition in the absence of the amide compound, the transition metal, and the nonionic colorant harmonizer.

5. The composition of claim 1 , wherein the transition metal is cobalt.

6. The composition of claim 5 , wherein the transition metal further comprises zinc.

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

8. The composition of claim 1 , wherein the base polymer comprises a polyester polymer or copolymer.

9. The composition of claim 1 , wherein the base polymer comprises polyethylene terephthalate or copolymer thereof.

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

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

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

13. The composition of claim 1 , wherein the amide compound has a structure of Formula I:

wherein each X is selected from the group consisting of O, S, and NH;
wherein each Y, each A, and each B are independently selected from the group consisting of N and CR 1 ;
wherein D, E, and F are independently selected from the group consisting of CH, N, O, and S;
wherein the symbol --- when used in conjunction with a bond line represents a single or a double bond; and
wherein each R 1 is independently selected from the group consisting of H, alkyl, aryl, electron withdrawing groups, electron releasing groups, and a transition metal.

14. The composition of claim 1 , wherein the amide compound has a structure of Formula II:

wherein each X is selected from the group consisting of O, S, and NH;
wherein each Y, each A, and each B are independently selected from the group consisting of N and CR 2 ;
wherein D, E, and F are independently selected from the group consisting of CH, N, O, and S;
wherein the symbol --- when used in conjunction with a bond line represents a single or a double bond; and
wherein each R 2 is independently selected from the group consisting of H, alkyl, aryl, electron withdrawing groups, electron releasing groups, and a transition metal.

15. The composition of claim 1 , wherein the amide compound is polymeric or copolymeric.

16. The composition of claim 1 , wherein the amide compound is polymeric or copolymeric and comprises a structure of Formula III:

wherein m is a positive integer greater than 10;
wherein n is an integer from 1 to 6; and
wherein R 3 is H or C1-C4 alkyl.

17. The composition of claim 16 , wherein n is 4.

18. The composition of claim 16 , wherein R 3 is H.

19. The composition of claim 1 , wherein the amide compound is a condensation product of meta-xylene diamine and adipic acid.

20. The composition of claim 1 , wherein the amide compound has a structure represented by a formula:
E-(L-E) x
wherein x is 0, 1, or 2;
wherein E has a structure of Formula IV or Formula V:

wherein L is a linking group of the formula —(O—R 21 ) z —O—, —(NH—R 21 ) z —NH—, —(NH—C(═O)R 22 ) t —NH, —NH—R 25 —NH(C(═O)R 26 NHR 25 NH) u —, —O—R 23 —O—(R 24 —C(═O)—O) s — where L is attached to a carbon atom of at least one Ar in Formula IV or where R 12 and/or R 13 of Formula V is L;
wherein Ar is aryl or heteroaryl;
wherein R 1 , R 2 , and R 11 are each independently, H, C 1 -C 12 alkyl, C 1 -C 6 alkoxy, C 6 -C 20 aryloxy, hydroxy, C 2 -C 6 alkenyl, NR 19 R 20 , acetyl, nitro, glyceryl, carbohydrate, —C(═O)H, L, or two R 1 or two R 2 groups can form a group of the formula —O—R 18 —O;
wherein R 3 , R 4 , R 14 , and R 15 are each H; R 5 to R 0 and R 16 , and R 17 are each, independently, H or C 1 -C 3 alkyl; R 12 and R 13 are each, independently, H, C 1 -C 6 alkyl, C 6 -C 20 aryl, C 1 -C 6 alkoxy, or L;
wherein R 18 is C 2 -C 6 alkyl; R 19 and R 20 are each, independently, H, C 1 -C 6 alkyl, or C 6 -C 20 aryl;
wherein R 2 , and R 24 are each, independently, C 1 -C 6 alkyl;
wherein R 22 , R 23 , R 25 and R 26 are each, independently, C 1 -C 6 alkyl or C 6 -C 20 aryl;
wherein n and p are independently 0 or an integer from 1 to 5;
wherein q is 0 or an integer from 1 to 4;
wherein s and z are independently 1, 2, or 3; and
wherein t and u are independently 1 or 2.

21. The composition of claim 20 , wherein the amide compound has a structure represented by a formula:

22. The composition of claim 21 , where n and p are each 0, 1, or 2 and R1 and R 2 are each independently H, C 1 -C 4 alkyl, hydroxy, C 1 -C 3 alkoxy, or carbohydrate.

23. The composition of claim 22 , wherein R 1 and R 2 are each independently H, methyl, ethyl, hydroxy, methoxy, ethoxy, or glucose.

24. The composition of claim 22 , wherein R 5 to R 10 are each H.

25. The composition of claim 24 , wherein R 1 and R 2 are each H.

26. The composition of claim 20 , wherein the amide compound has a structure represented by a formula:

27. The composition of claim 20 , wherein the amide compound has a structure represented by a formula:

Assignees

• Deshpande Girish N
• Plastipak Packaging Inc

Inventors

• Deshpande Girish N

Classifications

• C08K5/20

  Carboxylic acid amides · CPC title

• C08J2367/02

  Polyesters derived from dicarboxylic acids and dihydroxy compounds; (C08J2367/06 takes precedence) · CPC title

• B29C51/002

  characterised by the choice of material · CPC title

• C08K5/101

  of monocarboxylic acids · CPC title

• C08L77/06

  Polyamides derived from polyamines and polycarboxylic acids (C08L77/10 takes precedence) · CPC title