Oxygen scavengers, compositions comprising the scavengers, and articles made from the compositions
The disclosure relates to oxygen scavenging molecules, 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. An article of manufacture comprising a composition comprising:
(i) a base polymer;
(ii) a compound having a structure represented by a formula:
wherein Ar is aryl or heteroaryl;
wherein R 1 represents five groups independently selected from hydrogen, halogen, C1-C4 alkyl, electron withdrawing groups, electron donating groups, and a structure represented by a formula:
wherein Ar 2 is independently aryl or heteroaryl, and wherein Ar 2 is independently substituted with 0, 1, 2, or 3 groups independently selected from halogen, C1-C4 alkyl, electron withdrawing groups, and electron donating groups, and wherein valence is satisfied;
wherein R 10 is independently selected from hydrogen, C1-C4 alkyl, —C(O)R 20 , and —C(O)Ar 3 ;
wherein R 20 is C1-C4 alkyl;
wherein each Ar 3 is phenyl or naphthyl, and wherein each Ar 3 is independently substituted with 0, 1, 2, or 3 groups independently selected from halogen, C1-C4 alkyl, —CO 2 R 30 , electron withdrawing groups, and electron donating groups, and wherein valence is satisfied;
wherein R 30 , when present, is selected from hydrogen, C1-C4 alkyl, —(CH 2 ) n OH, and —CH 2 Ar 4 ;
wherein n is an integer selected from 1 or 2;
wherein Ar 4 , when present, is aryl substituted with 0, 1, 2, and 3 groups selected from halogen, C1-C4 alkyl, and —C(O)NHCH 2 Ar 5 ;
wherein each Ar 5 , when present, is aryl substituted with 0, 1, 2, or 3 groups independently selected from halogen, C1-C4 alkyl, electron withdrawing groups, electron donating groups, and a structure represented by a formula:
wherein each R 40 , when present, is independently selected from hydrogen, C1-C4 alkyl, electron withdrawing groups, and electron donating groups;
wherein each Ar 6 , when present, is aryl substituted with 0, 1, 2, and 3 groups independently selected from hydrogen, C1-C4 alkyl, electron withdrawing groups, and electron donating groups;
wherein R 2 is independently selected from hydrogen, C1-C4 alkyl, —C(O)R 50 , and —C(O)Ar 7 ;
wherein R 50 is C1-C4 alkyl;
wherein each Ar 7 is aryl substituted with 0, 1, 2, and 3 groups independently selected from hydrogen, C1-C4 alkyl, and electron withdrawing groups, and electron donating groups, and valence is satisfied; and
(iii) at least one transition metal in a positive oxidation state.
2. A method of making an oxygen scavenging polymer comprising the steps of:
(a) providing a monomer comprising a moiety represented by a formula:
wherein n is 2, 3, 4, 5, or 6;
wherein Ar is aryl or heteroaryl;
wherein R 1 represents 6-n groups independently selected from hydrogen, halogen, C1-C4 alkyl, electron withdrawing groups, and electron donating groups; and
(b) polymerizing polyethylene terephthalate in the presence of the monomer, or functionalizing polyethylene terephthalate with the monomer.
3. The method of claim 2 , wherein the method comprises polymerizing polyethylene terephthalate in the presence of the monomer.
4. The method of claim 2 , wherein the method comprises functionalizing polyethylene terephthalate with the monomer.
5. A wall of a package comprising at least one layer, said layer comprising a composition comprising:
(i) a base polymer;
(ii) a compound having a structure represented by a formula:
wherein Ar is aryl or heteroaryl;
wherein R 1 represents five groups independently selected from hydrogen, halogen, C1-C4 alkyl, electron withdrawing groups, electron donating groups, and a structure represented by a formula:
wherein Ar 2 is independently aryl or heteroaryl, and wherein Ar 2 is independently substituted with 0, 1, 2, or 3 groups independently selected from halogen, C1-C4 alkyl, electron withdrawing groups, and electron donating groups, and wherein valence is satisfied;
wherein R 10 is independently selected from hydrogen, C1-C4 alkyl, —C(O)R 20 , and —C(O)Ar 3 ;
wherein R 20 is C1-C4 alkyl;
wherein each Ar 3 is phenyl or naphthyl, and wherein each Ar 3 is independently substituted with 0, 1, 2, or 3 groups independently selected from halogen, C1-C4 alkyl, —CO 2 R 30 , electron withdrawing groups, and electron donating groups, and wherein valence is satisfied;
wherein R 30 , when present, is selected from hydrogen, C1-C4 alkyl, —(CH 2 ) n OH, and —CH 2 Ar 4 ;
wherein n is an integer selected from 1 or 2;
wherein Ar 4 , when present, is aryl substituted with 0, 1, 2, and 3 groups selected from halogen, C1-C4 alkyl, and —C(O)NHCH 2 Ar 5 ;
wherein each Ar 5 , when present, is aryl substituted with 0, 1, 2, or 3 groups independently selected from halogen, C1-C4 alkyl, electron withdrawing groups, electron donating groups, and a structure represented by a formula:
wherein each R 40 , when present, is independently selected from hydrogen, C1-C4 alkyl, electron withdrawing groups, and electron donating groups;
wherein each Ar 6 , when present, is aryl substituted with 0, 1, 2, and 3 groups independently selected from hydrogen, C1-C4 alkyl, electron withdrawing groups, and electron donating groups;
wherein R 2 is independently selected from hydrogen, C1-C4 alkyl, —C(O)R 50 , and —C(O)Ar 7 ;
wherein R 50 is C1-C4 alkyl;
wherein each Ar 7 is aryl substituted with 0, 1, 2, and 3 groups independently selected from hydrogen, C1-C4 alkyl, and electron withdrawing groups, and electron donating groups, and valence is satisfied; and
(iii) at least one transition metal in a positive oxidation state.
6. The wall of claim 5 , wherein said wall comprises
(a) one or more outer layers; and
(b) one or more inner layers;
wherein at least one of said inner or at least one of said outer layers comprises the composition.