Dendritic oxygen scavenging polymer
View Patent ↗An oxygen-scavenging composition is provided that includes an oxygen-scavenging polymer and a catalyst. The oxygen-scavenging polymer, which in preferred embodiments is suitable for use in packaging articles, is a dendritic polymer having one or more oxygen-scavenging groups.
1. An article for packaging a food or beverage product, the article comprising:
one or more layers of a composition comprising:
an oxygen-scavenging dendritic polymer having a globular morphology with a degree of branching of at least 0.2, and a plurality of oxygen-scavenging groups located at terminal units of the dendritic polymer; and
an oxidation catalyst comprising a transition metal, wherein the oxidation catalyst is configured to catalyze an oxygen-scavenging reaction with the oxygen-scavenging groups of the dendritic polymer to reduce oxygen contamination of the package food or beverage product.
2. The article of claim 1 , wherein the dendritic polymer has a degree of branching of at least 0.4.
3. The article of claim 1 , wherein the dendritic polymer comprises a polyamide, polyester, polyether, polyolefin, vinylic polymer, polyimine, polysiloxane, polyurethane, polythioether, polyarylalkylenes, polysilane, polycarbonate, polysulfone, polyimide, polyesterimide, polyesteramide, a mixture thereof, or a copoloymer thereof.
4. The article of claim 1 , wherein the dendritic polymer comprises a polyester.
5. The article of claim 1 , wherein the dendritic polymer comprises at least about 0.5 weight percent of the article.
6. The article of claim 1 , wherein at least one of the oxygen-scavenging groups is attached to at least one other portion of the dendritic polymer by an amide, carbonate, carbonate ester, ester, ether, urea, urethane, a substituted or unsubstituted hydrocarbon linking group, or a combination thereof.
7. The article of claim 1 , wherein the oxygen-scavenging group comprises an organic group having at least one carbon-carbon double bond, an organic group that is a reaction product of metaxylene diamine, or a mixture thereof.
8. The article of claim 1 , wherein the dendritic polymer includes at least one structural unit represented by the schematic formula:
—X—Y—Z
wherein:
X comprises a divalent organic linking group that links the —X—Y—Z group to another portion of the dendritic polymer;
Y comprises one of the below structures:
—W—C(R 3 )=C(R 4 )—C(R 5 R 6 )—C(R 7 )=C(R 8 )—,
—W—C(R 3 )=C(R 4 )—C(R 7 )=C(R 8 )—, or mixtures of the above formulas,
wherein W, if present, is a divalent organic group and the R groups each independently denote one of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkenyl group; and
Z represents hydrogen or a monovalent organic group.
9. The article of claim 1 , wherein the composition comprises between about 10 and about 1,000 ppm by weight of the oxidation catalyst.
10. The article of claim 9 , wherein the oxidation catalyst further comprises a complex of a transition metal, a photoinitiator, or a mixture thereof.
11. The article of claim 9 , wherein the oxidation catalyst comprises a cobalt catalyst.
12. The article of claim 1 , wherein the composition further comprises a second polymer.
13. The article of claim 12 , wherein the second polymer comprises a polyester.
14. The article of claim 1 , wherein the composition comprises a thermoplastic composition.
15. The article of claim 1 , wherein the article comprises a monolayer article.
16. The article of claim 1 , wherein the dendritic polymer is a reaction product of a reactant of the formula A m —L—B n , wherein:
A and B denote reactive functional groups capable of reacting with one another to form a covalent bond;
m is an integer of 1 or more;
n is an integer of 2 or more; and
L denotes a group linking A and B.
17. The article of claim 16 , wherein:
L comprises a carbon atom, a silicon atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted aryl group, or a combination thereof; and
A and B independently comprise an amine, carboxylic, hydroxyl, isocyanate, sulphonic acid, thiol, or unsaturated group.
18. The article of claim 1 , wherein the composition used to form the one or more layers, when formed into a monolayer 591 ml carbonated soft drink beverage bottle having a total wall thickness of about 0.025 cm, exhibits less than 0.05 cc/pkg/day transmission of O 2 .
19. The article of claim 1 , wherein the dendritic polymer has a degree of branching of at least 0.7.
20. The article of claim 1 , wherein the oxygen-scavenging group comprises an organic group having at least one carbon-carbon double bond and the dendritic polymer has an iodine value of between 10 and 200.
21. The article of claim 1 , wherein the oxygen-scavenging groups comprises a reaction product of an unsaturated fatty acid.
22. The article of claim 21 , wherein the unsaturated fatty acid comprises arichidonic acid, erucic acid, oleic acid, palmitoleic acid, ricinoleic acid, licanic acid, linolenic acid, eleostearic acid, linoleic acid, or conjugated linoleic acid.