Oxygen-scavenging materials and articles formed therefrom
View Patent ↗An oxygen-scavenging component and methods for producing the oxygen-scavenging component are provided. The oxygen-scavenging component, which in preferred embodiments is suitable for use in packaging articles, includes an oxygen-scavenging group preferably having at least one double bond. The oxygen-scavenging component may be combined with a polymer and/or an oxidation catalyst to form an oxygen-scavenging composition.
1. A composition, comprising:
a thermoplastic polymer;
an oxygen-scavenging polymer comprising a condensation polymer having an unsaturated bicyclic group; and
an oxidation catalyst.
2. The composition of claim 1 , wherein the bicyclic group includes at least one double bond located between atoms of a ring.
3. The composition of claim 1 , wherein the bicyclic group comprises a structure represented by the nomenclature expression:
bicyclo [x,y,z]alkene
wherein:
x is 2 or more, and
y and z are each at least 1.
4. The composition of claim 3 , wherein:
x is 2 or 3, and
y and z are independently 1 or 2.
5. The composition of claim 1 , wherein the bicyclic group comprises bicyclo[2.1.1]hexene, bicyclo[2.2.1]heptene, bicyclo[2.2.1]heptadiene, bicyclo[2.2.2]octene, bicyclo[2.2.2]octadiene, or a mixture thereof.
6. The composition of claim 1 , wherein the condensation polymer includes both condensation and addition linkages or segments.
7. The composition of claim 1 , wherein the condensation polymer comprises a thermoplastic polymer.
8. The composition of claim 1 , wherein the condensation polymer comprises one or more polyester, copolyester, polycarbonate, poly(ethylene oxide), poly(epsilon- caprolactam), polyurethane, polyepoxide, polylactone, polyoxymethylene, polyamide, polyimide, polysulfone, polyaminoacid, polydimethylsiloxane, derivative thereof, or mixture thereof.
9. The composition of claim 1 , wherein the condensation polymer comprises a polyester polymer, a copolyester polymer, or a combination thereof.
10. The composition of claim 9 , wherein the condensation polymer comprises a polyethylene terephthalate.
11. The composition of claim 1 , wherein a pair of condensation linkages attach a polymer precursor including the bicyclic group to a backbone of the oxygen- scavenging polymer.
12. The composition of claim 1 , wherein the unsaturated bicyclic group is present in a condensation monomer.
13. The composition of claim 1 , wherein the composition comprises at least about 25 parts per million of the oxidation catalyst.
14. The composition of claim 1 , wherein the oxidation catalyst comprises one or more transition metals, transition metal complexes, or mixtures thereof.
15. The composition of claim 1 , wherein the oxidation catalyst comprises a cobalt catalyst.
16. The composition of claim 15 , wherein:
the oxygen-scavenging polymer comprises a polyester polymer and the composition includes at least 1% by weight of the oxygen-scavenging polyester polymer; and
the composition includes at least 25 ppm of the oxidation catalyst.
17. The composition of claim 16 , wherein the unsaturated bicyclic group is present in a structural unit derived from an unsaturated fatty acid or unsaturated succinic anhydride derivative.
18. The composition of claim 1 , wherein the composition is a melt blend.
19. The composition of claim 1 , wherein the composition is in the form of solid thermoplastic particles.
20. A composition, comprising:
a thermoplastic polymer;
a component that includes an unsaturated bicyclic oxygen-scavenging group that is a Diels-Alder reaction product of:
a ring of a conjugated diene component, the ring having at least two conjugated double bonds, and
a double or triple bond of an unsaturated component, wherein the unsaturated component comprises an acid, or anhydride or easter thereof, an alcohol, an amine, an isocyanate, a thiol, or a combination thereof; and
at least about 10 ppm of an oxidation catalyst.
21. The composition of claim 20 , wherein the component comprises a formable condensation polymer that includes the bicyclic oxygen-scavenging group.
22. An oxygen-scavenging composition comprising:
a thermoplastic polymer;
a condensation polymer having an oxygen-scavenging bicyclic group that includes at least one carbon-carbon double bond with a heat of hydrogenation at least about as high as the heat of hydrogenation of bicyclo[2.2.1]heptene; and
an oxidation catalyst.