Oxygen scavenging composition
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, includes a base polymer having a backbone, and an unsaturated side chain attached to the backbone. In one embodiment, the side chain comprises an unsaturated fatty-acid.
1. A packaging article including a layer comprising:
an oxygen-scavenging polymer that includes:
a base polymer having a backbone that includes at least one heteroatom, wherein the backbone comprises a polyester backbone having one or more aromatic groups, and
an unsaturated fatty-acid-based side chain attached to the backbone and having two or more carbon-carbon double bonds; and
an oxidation catalyst;
wherein the base polymer comprises one or more polyesters, copolyesters, mixtures thereof, or derivatives thereof.
2. The packaging article of claim 1 , wherein the oxygen-scavenging polymer has at least one structural unit represented by the schematic formula:
wherein,
-[BACKBONE SEGMENT]- depicts a segment of the backbone;
the —X—Y—Z side chain is formed using as a feedstock a polyunsaturated fatty acid;
X depicts a divalent organic linking group connected to the backbone;
Y depicts a divalent oxygen-scavenging group including two or more carbon-carbon double bonds; and
Z depicts hydrogen or a monovalent organic group.
3. The packaging article of claim 2 , wherein X comprises an ester, amide, urethane, ether, urea, carbonate ester, or hydrocarbyl linking group.
4. The packaging article of claim 2 , wherein the Y group comprises one of the formulas:
—W—C(R 1 )═C(R 2 )—C(R 3 R 4 )—C(R 5 )═C(R 6 )—; or
—W—C(R 1 )═C(R 2 )—C(R 5 )═C(R 6 )—; or mixtures of the above formulas,
wherein W is optional and, if present, is a divalent organic group and the R groups each 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.
5. The packaging article of claim 1 , wherein the unsaturated fatty-acid-based side chain has a molecular weight from about 67 to 1,000.
6. The packaging article of claim 1 , wherein the unsaturated fatty-acid-based side chain is formed using as a feedstock a fatty acid selected from arichidonic, licanic, linolenic, eleostearic, linoleic, or conjugated linoleic acid, or a mixture or combination of these fatty acids.
7. The packaging article of claim 1 , wherein the unsaturated fatty-acid-based side chains constitute between 1 and 60 weight percent of the oxygen-scavenging polymer.
8. The packaging article of claim 1 , wherein the oxidation catalyst comprises a transition metal, a complex of a transition metal, a photoinitiator or a mixture thereof.
9. The packaging article of claim 1 , wherein the oxidation catalyst comprises cobalt, cobalt oxide, cobalt chloride, a cobalt salt of a long chain acid, or a mixture thereof.
10. The packaging article of claim 1 , wherein the article comprises a single-layer article.
11. The packaging article of claim 1 , wherein the oxygen-scavenging polymer comprises a reaction product of a fatty-acid diol adduct having two or more carbon-carbon double bonds and either (i) a di-acid compound or (ii) a di-isocyanate compound.
12. A packaging article including a layer comprising:
an oxygen-scavenging polymer that includes:
a polyester or copolyester base polymer, and
an unsaturated fatty-acid-based side chain attached to the backbone, wherein the side chain includes two or more carbon-carbon double bonds; and
an oxidation catalyst comprising cobalt, cobalt oxide, cobalt chloride, a cobalt salt of a long chain acid, or a mixture thereof.
13. The packaging article of claim 12 , wherein the unsaturated fatty-acid-based side chains have a molecular weight from about 67 to 1,000 and constitute between 1 and 60 weight percent of the oxygen-scavenging polymer.
14. The packaging article of claim 12 , wherein the article comprises a single-layer article selected from a bottle, cup, bowl, container, film, wrap, liner, coating, tray, carton or bag.
15. A packaging article including a layer comprising: an oxygen-scavenging polymer that includes:
a base polymer having a backbone that includes at least one heteroatom, and
an unsaturated fatty-acid-based side chain attached to the backbone and having two or more carbon-carbon double bonds; and
an oxidation catalyst;
wherein the oxygen-scavenging polymer has at least one structural unit represented by the schematic formula:
wherein,
-[BACKBONE SEGMENT]- depicts a segment of the backbone;
the —X-Y-Z side chain is formed using as a feedstock a polyunsaturated fatty acid; X depicts a divalent organic linking group connected to the backbone;
Y depicts a divalent oxygen-scavenging group including two or more carbon-carbon double bonds; and
Z depicts hydrogen or a monovalent organic group; and
wherein the base polymer comprises a polyester or a copolyester, X is an ester linkage, and the —X—Y—Z side chain has a molecular weight of from about 99 to 400.
16. The packaging article of claim 15 , wherein the article comprises a single-layer article selected from a bottle, cup, bowl, container, film, wrap, liner, coating, tray, carton or bag.