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 melt blended polymer composition comprising:
a. a base polymer;
b. at least one compound having a structure of Formula I-VI present in an amount of from about 0.10 to about 10 weight percent of the composition; and
c. a transition metal in a positive oxidation state, the metal present in an amount of from about 10 ppm to about 400 ppm;
wherein Formula I and Formula II are compounds having the following structures:
wherein the symbol --- when used in conjunction with a bond line represents a single or a double bond;
wherein n is 3, 4, 5, or 6;
wherein m is an integer from 0 to 6-n;
wherein each X is independently 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, CR 1 , and CR 2 ;
wherein D, E, and F are independently selected from the group consisting of CH, N, O, and S; and
wherein each R 1 and each R 2 is independently selected from the group consisting of H, alkyl, aryl, electron withdrawing groups, electron releasing groups, and a transition metal;
Formula III and Formula IV are compounds having the following structures:
wherein the symbol --- when used in conjunction with a bond line represents a single or a double bond;
wherein each n is independently 1-5;
wherein m is an integer from 0 to 5-n;
wherein each X is independently 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, CR 1 and CR 2 ;
wherein D, E, and F are independently selected from the group consisting of CH, N, O, and S;
wherein each R 1 and each R 2 is independently selected from the group consisting of H, alkyl, aryl, electron withdrawing groups, electron releasing groups, and a transition metal; and
wherein L is a divalent linking group selected from C2-C12 aliphatic or cyclic ether, C2-C12 aliphatic or cyclic amide, C6 to C12 aromatic amide, C2-C12 aliphatic or cyclic amine, C6-C12 aromatic amine, C2-C12 aliphatic or cyclic ester and C6 to C12 aromatic ester;
and Formula V and VI are compounds having the following structures:
wherein the symbol --- when used in conjunction with a bond line represents a single or a double bond;
wherein each n is independently 0-5;
wherein m in is an integer from 0 to 5-n;
wherein each X is independently 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, CR 1 , and CR 2 ;
wherein D, E, and F are independently selected from the groups consisting of CH, N, O, and S;
wherein each R 1 and each R 2 is independently selected from the group consisting of H, alkyl, aryl, electron withdrawing groups, electron releasing groups, and a transition metal; and
wherein L is a divalent linking group selected from C2-C12 aliphatic or cyclic ether, C2-C12 aliphatic or cyclic amide, C6 to C12 aromatic amide, C2-C12 aliphatic or cyclic amine, C6-C12 aromatic amine, C2-C12 aliphatic or cyclic ester and C6 to C12 aromatic ester.
2. The composition of claim 1 , wherein the composition has an OTR of less than about 0.1 cc/package/day.
3. The composition of claim 1 , further comprising a visually effective amount of colorant.
4. The composition of claim 1 , wherein the transition metal is cobalt.
5. The composition of claim 4 , wherein the transition metal further comprises zinc.
6. The composition of claim 1 , wherein the concentration of transition metal is 30 to 150 ppm.
7. The composition of claim 1 , wherein the base polymer comprises a polyester polymer or copolymer.
8. The composition of claim 1 , wherein the base polymer comprises polyethylene terephthalate or copolymer thereof.
9. The composition of claim 1 , wherein the compound having a structure of Formula I-VI is present in an amount of about 1 to about 10 weight percent based on the weight of the composition.
10. The composition of claim 1 , wherein the compound having a structure of Formula I-VI is present in an amount of about 1 to about 5 weight percent based on the weight of the composition.
11. The composition of claim 1 , wherein the compound having a structure of Formula I-VI is present in an amount of about 1 to about 3 weight percent based on the weight of the composition.
12. An article comprising a composition of a base polymer; at least one compound having a structure of Formula I-VI present in an amount of from about 0.10 to about 10 weight percent of the composition; and a transition metal in a positive oxidation state, the metal present in an amount of from about 10 ppm to about 400 ppm;
wherein Formula I and Formula II are compounds having the following structures:
wherein the symbol --- when used in conjunction with a bond line represents a single or a double bond;
wherein n is 3, 4, 5, or 6;
wherein m is an integer from 0 to 6-n;
wherein: each X is independently 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, CR 1 , and CR 2 ;
wherein D, E, and F are independently selected from the group consisting of CH, N, O, and S; and
wherein each R 1 and each R 2 is independently selected from the group consisting of H, alkyl, aryl, electron withdrawing groups, electron releasing groups, and a transition metal;
Formula III and Formula IV are compounds having the following structures:
wherein the symbol --- when used in conjunction with a bond line represents a single or a double bond;
wherein each n is independently 1-5;
wherein m in is an integer from 0 to 5-n;
wherein each X is independently 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, CR 1 , and CR 2 ;
wherein D, E, and F are independently selected from the group consisting of CH, N, O, and S;
wherein each R 1 and each R 2 is independently selected from the group consisting of H, alkyl, aryl, electron withdrawing groups, electron releasing groups, and a transition metal; and
wherein L is a divalent linking group selected from C2-C12 aliphatic or cyclic ether, C2-C12 aliphatic or cyclic amide, C6 to C12 aromatic amide, C2-C12 aliphatic or cyclic amine, C6-C12 aromatic amine, C2-C12 aliphatic or cyclic ester and C6 to C12 aromatic ester;
and Formula V and VI are compounds having the following structures:
wherein the symbol --- when used in conjunction with a bond line represents a single or a double bond:
wherein each n is independently 0-5;
wherein m is an integer from 0 to 5-n;
wherein each X is independently 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, CR 1 , and CR 2 ;
wherein D, E, and F are independently selected from die group consisting of CH, N, O, and S;
wherein each R 1 and each R 2 is independently selected from the group consisting of H, alkyl, aryl, electron withdrawing groups, electron releasing groups, and a transition metal; and
wherein L is a divalent linking group selected from C2-C12 aliphatic or cyclic ether, C2-C12 aliphatic or cyclic amide, C6 to C12 aromatic amide, C2-C12 aliphatic or cyclic amine, C6-C12 aromatic amine, C2-C12 aliphatic or cyclic ester and C6 to C12 aromatic ester.
13. The article of claim 12 , dimensioned as a vessel.
14. The article of claim 12 , dimensioned as a film.