Thermoplastic polymers comprising oxygen scavenging molecules
View Patent ↗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.
1. A thermoplastic polymer comprising an allylic or benzylic amide compound covalently bonded as a repeating unit in the polymer chain, covalently bonded thereto as a side-chain pendant group, or covalently bonded thereto as an end group of the polymer;
wherein the repeating unit, end group, or the side-chain pendant group of the polymer comprises a residue represented by the formula:
wherein for formula (a), 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 carboxylic acid, amine, nitro, cyano, hydroxyl, H, alkyl, aryl, electron withdrawing groups, electron releasing groups, and a transition metal;
wherein for formula (b), the symbol --- when used in conjunction with a bond line represents a single or a double bond; 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 carboxylic acid, amine, nitro, cyano, hydroxyl, H, alkyl, aryl, electron withdrawing groups, electron releasing groups, and a transition metal;
wherein for formula (c), 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 carboxylic acid, amine, nitro, cyano, hydroxyl, 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;
wherein for formula (d), 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 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 carboxylic acid, amine, nitro, cyano, hydroxyl, 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; or
wherein for formula (e), 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, and electron releasing groups.
2. A composition comprising the polymer of claim 1 .
3. The composition of claim 2 , further comprising a base polymer.
4. The composition of claim 2 , wherein the base polymer is a polyester.
5. The composition of claim 2 , wherein the base polymer is polyethylene terephthalate.
6. The composition of claim 2 , wherein the composition has an OTR of less than about 0.1cc/m 2 /day.
7. The composition of claim 2 , further comprising a visually effective amount of colorant.
8. The composition of claim 2 , 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.
9. The composition of claim 8 , wherein the transition metal is cobalt.
10. The composition of claim 8 , wherein the transition metal further comprises zinc.
11. The composition of claim 8 , wherein the concentration of transition metal is 30 to 150 ppm.
12. An article made from the composition of claim 2 .
13. The article of claim 12 , dimensioned as a vessel.
14. The article of claim 12 , dimensioned as a film.