Oxygen-Scavenging Materials and Articles Formed Therefrom

Abstract

An oxygen-scavenging composition is provided that includes an oxygen-scavenging component and a catalyst. The oxygen-scavenging component, which in preferred embodiments is suitable for use in packaging articles, includes two or more oxygen-scavenging groups having different scavenging properties. In one embodiment, one of the oxygen-scavenging groups is an unsaturated bicyclic group.

What is claimed is: 
     
         1 . A composition comprising:
 an oxygen-scavenging component including:
 a polyamide oxygen-scavenging group, and 
 a bicyclic oxygen-scavenging group having at least one double bond located between atoms of a ring, 
 wherein at least one of the polyamide or bicyclic oxygen-scavenging groups is included in a polymer; and 
   an oxidation catalyst.   
     
     
         2 . The composition of  claim 1 , wherein the polyamide oxygen-scavenging group and the bicyclic oxygen-scavenging group are present on different polymers. 
     
     
         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 bicyclic group is included in a polymer having a condensation backbone. 
     
     
         7 . The composition of  claim 6 , wherein the condensation backbone comprises a polyester, copolyester, polyamide, polycarbonate, polyether, polyurethane, polyepoxide, polylactone, a derivative or copolymer thereof, or a mixture thereof. 
     
     
         8 . The composition of  claim 6 , wherein the polymer including the bicyclic group comprises a polyester polymer. 
     
     
         9 . The composition of  claim 6 , wherein the bicyclic group comprises a pendant group attached to the condensation backbone. 
     
     
         10 . The composition of  claim 9 , wherein the pendant group is a reaction product of ingredients including an unsaturated fatty acid. 
     
     
         11 . The composition of  claim 1 , wherein the polyamide group comprises a structural unit represented by the below structural formula (I):
   -arylene-C(HR 1 )—N(R 2 )—(C═O)—,
   wherein R 1  and R 2  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 or cycloalkenyl group.   
     
     
         12 . The composition of  claim 1 , wherein the composition comprises at least about 25 parts per million of the oxidation catalyst. 
     
     
         13 . The composition of  claim 12 , wherein the oxidation catalyst comprises one or more transition metals, transition metal complexes, or mixtures thereof. 
     
     
         14 . The composition of  claim 1 , wherein the oxidation catalyst comprises a cobalt catalyst. 
     
     
         15 . A packaging article, comprising the composition of  claim 1 . 
     
     
         16 . The packaging article of  claim 15 , wherein the article comprises a single-layer packaging article. 
     
     
         17 . The packaging article of  claim 15 , wherein the packaging article comprises a multi-layer packaging article. 
     
     
         18 . The packaging article of  claim 15 , wherein the article comprises about 15 wt-% or less of the oxygen-scavenging component. 
     
     
         19 . A method, comprising:
 providing:
 a conjugated diene component, and 
 an unsaturated component; and 
   forming a first oxygen-scavenging polymer that includes a bicyclic group that is a Diels-Alder reaction product of the above components, wherein the bicyclic group includes at least one ring having a double bond located between atoms of the ring; and   forming an oxygen-scavenging composition that comprises:
 (i) the first oxygen-scavenging polymer; 
 (ii) at least one of:
 (a) a structural unit represented by the below structural formula (I):
   -arylene-C(HR 1 )—N(R 2 )—(C═O)—,
 
 wherein R 1  and R 2  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 or cycloalkenyl group; or 
 
 (b) an unsaturated oxygen-scavenging group that includes at least one carbon-carbon double bond with a heat of hydrogenation of less than or equal to that of cyclohexene; 
 wherein the above (a) or (b) are present on the first oxygen-scavenging polymer or a second oxygen-scavenging polymer; and 
 
 (iii) an oxidation catalyst. 
   
     
     
         20 . A composition comprising:
 an oxygen-scavenging component having at least one of:
 a first oxygen-scavenging comprising a cyclic or bicyclic oxygen-scavenging group having at least one carbon-carbon double bond located between atoms of a ring, wherein:
 the carbon-carbon double bond has a heat of hydrogenation of at least 33 kcal/mole, and 
 the cyclic or bicyclic group is included in a polymer having a condensation backbone; and 
 
 a second oxygen-scavenging group comprising:
 one or more of a structural unit represented by the formula:
   -arylene-C(HR 1 )—N(R 2 )—(C═O)—,
 
 
 wherein R 1  and R 2  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 or cycloalkenyl group, or an unsaturated oxygen-scavenging group that includes at least one carbon-carbon double bond
 with a heat of hydrogenation of 32 kcal/mole or less; and 
 
 
   an oxidation catalyst.