Polymer with pendent cyclic olefinic functions for oxygen scavenging packaging
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
B29D-022/00
B29D-023/00
B32B-001/08
B32B-001/00
출원번호
US-0127316
(1998-07-31)
발명자
/ 주소
Ching,Ta Yen
Goodrich,Joseph L.
Leonard,James P.
Russell,Kenneth W.
출원인 / 주소
Chevron Phillips Chemical Co. LP
인용정보
피인용 횟수 :
14인용 특허 :
29
초록
A family of polymers containing selected cyclic allylic pendent groups for oxygen scavenging packaging which has minimal organoleptic by-products after oxidation.
대표청구항▼
What is claimed is: 1. A compound, comprising a polymeric backbone, cyclic olefinic pendent groups and linking groups linking the olefinic pendent groups to the polymeric backbone, and comprising the formula (II) as follows: wherein P+T+Q is 100 mol % of the compound; P, T, and Q are each greate
What is claimed is: 1. A compound, comprising a polymeric backbone, cyclic olefinic pendent groups and linking groups linking the olefinic pendent groups to the polymeric backbone, and comprising the formula (II) as follows: wherein P+T+Q is 100 mol % of the compound; P, T, and Q are each greater than 0 mol % of the compound; Z is selected from the group consisting of an aryl group;--(C═O)OR1;--O(C═O)R 1; and an alkyl aryl group: where R4 is selected from the group consisting of-CH3, ethyl, and hydrogen; R1 is selected from the group consisting of hydrogen, methyl, ethyl,--C3H7 and--C4H9; R2 and R3 are selected from the group consisting of hydrogen and methyl; X is selected from the group consisting of--O--,--NH--,--(C═O)O--,--(C═O)NH--,--(C═ O)S--,--O(C═O)--and--(CHR)L--; L is an integer in the range from 1 to 6; Y is--(CHR)n--, where n is an integer in the range from 0 to 12, R being selected from the group consisting of hydrogen, methyl and ethyl; where q1, q2, q3, q4, and r are selected from the group consisting of hydrogen, methyl, and ethyl; and where m is--(CH2)n--and where n is an integer in the range from 0 to 4; and wherein when r is hydrogen, at least one of q1, q2, q3 and q4 is hydrogen. 2. The compound of claim 1, wherein the polymeric backbone comprises monomers selected from the group consisting of ethylene and styrene. 3. The compound of claim 1, wherein the cyclic olefinic pendent groups are selected from the group consisting of cyclohexene-4-methylene radical, 1-methyl cyclohexene-4-methylene radical, 2-methyl cyclohexene-4-methylene radical, 5-methyl cyclohexene-4-methylene radical, 1,2-dimethyl cyclohexene-4-methylene radical, 1,5-dimethyl cyclohexene-4-methylene radical, 2,5-dimethyl cyclohexene-4-methylene radical, 1,2,5-trimethyl cyclohexene-4-methylene radical, cyclohexene-4-ethylene radical, 1-methyl cyclohexene-4-ethylene radical, 2-methyl cyclohexene-4-ethylene radical, 5-methyl cyclohexene-4-ethylene radical, 1,2-dimethyl cyclohexene-4-ethylene radical, 1,5-dimethyl cyclohexene-4-ethylene radical, 2,5-dimethyl cyclohexene-4-ethylene radical, 1,2,5-trimethyl cyclohexene-4-ethylene radical, cyclohexene-4-propylene radical, 1-methyl cyclohexene-4-propylene radical, 2-methyl cyclohexene-4-propylene radical, 5-methyl cyclohexene-4-propylene radical, 1,2-dimethyl cyclohexene-4-propylene radical, 1,5-dimethyl cyclohexene-4-propylene radical, 2,5-dimethyl cyclohexene-4-propylene radical, 0,1,2,5-trimethyl cyclohexene-4-propylene radical, cyclopentene-4-methylene radical, 1-methyl cyclopentene-4-methylene radical, 3-methyl cyclopentene-4-methylene radical, 1,2-dimethyl cyclopentene-4-methylene radical, 3,5-dimethyl cyclopentene-4-methylene radical, 1,3-dimethyl cyclopentene-4-methylene radical, 2,3-dimethyl cyclopentene-4-methylene radical, 1,2,3-trimethyl cyclopentene-4-methylene radical, 1,2,3,5-tetramethyl cyclopentene-4-methylene radical, cyclopentene-4-ethylene radical, 1-methyl cyclopentene-4-ethylene radical, 3-methyl cyclopentene-4-ethylene radical, 1,2-dimethyl cyclopentene-4-ethylene radical, 3,5-dimethyl cyclopentene-4-ethylene radical, 1,3-dimethyl cyclopentene-4-ethylene radical, 2,3-dimethyl cyclopentene-4-ethylene radical, 1,2,3-trimethyl cyclopentene-4-ethylene radical, 1,2,3,5-tetramethyl cyclopentene-4-ethylene radical, cyclopentene-4-propylene radical, 1-methyl cyclopentene-4-propylene radical, 3-methyl cyclopentene-4-propylene radical, 1,2-dimethyl cyclopentene-4-propylene radical, 3,5-dimethyl cyclopentene-4-propylene radical, 1,3-dimethyl cyclopentene-4-propylene radical, 2,3-dimethyl cyclopentene-4-propylene radical, 1,2,3-trimethyl cyclopentene-4-propylene radical, and 1,2,3,5-tetramethyl cyclopentene-4-propylene radical. 4. The compound of claim 1, wherein the compound is an ethylene/methyl acrylate/cyclohexenyl methyl acrylate terpolymer. 5. The compound of claim 1, wherein the cyclic olefinic pendent groups are grafted onto the linking groups of the polymeric backbone by an esterification, transesterification, amidation or transamidation reaction. 6. The compound of claim 5, wherein the esterification, transesterification, amidation or transamidation reaction is a solution reaction or a reactive extrusion. 7. The compound of claim 5, wherein the esterification, transesterification, amidation or transamidation reaction is catalyzed by a catalyst selected from the group consisting of strong non-oxidizing acids, tertiary amines, Group I alkoxides, Group IVB alkoxides, and Group IVA organometallics. 8. The compound of claim 7, wherein the catalyst is selected from a group consisting of toluene sulfonic acid, sodium methoxide, tetrabutyl titanate, tetraisopropyl titanate, tetra-n-propyl-titanate, tetraethyl titanate, 2-hydroxy-pyridine and dibutyltin dilaurate. 9. An oxygen scavenging composition, comprising a compound comprising a polymeric backbone, cyclic olefinic pendent groups, and linking groups linking the olefinic pendent groups to the polymeric backbone, and a transition metal catalyst; wherein the transition metal catalyst is a metal salt, and the compound comprises the formula (II) as follows: wherein P+T+Q is 100 mol % of the compound; P, T, and Q are each greater than 0 mol % of the compound; Z is selected from the group consisting of an aryl group;--(C═O)OR1;--O(C═O)R 1; and an alkyl aryl group: where R4 is selected from the group consisting of--CH3, ethyl, and hydrogen; R1 is selected from the group consisting of hydrogen, methyl, ethyl,--C3H7 and--C4H9; R2 and R3 are selected from the group consisting of hydrogen and methyl; X is selected from the group consisting of--O--,--NH--,--(C═O)O--,--(C═O)NH--,--(C═ O)S--,--O(C═O)--and--(CHR)L--; L is an integer in the range from 1 to 6; Y is--(CHR)n--, where n is an integer in the range from 0 to 12, R being selected from the group consisting of hydrogen, methyl and ethyl; where q1, q2, q3, q4, and r are selected from the group consisting of hydrogen, methyl, and ethyl; and where m is--(CH2)n--and where n is an integer in the range from 0 to 4; and wherein when r is hydrogen, at least one of q1, q2, q3 and q4 is hydrogen. 10. A composition according to claim 9, wherein the polymeric backbone is ethylenic and the linking groups are selected from the group consisting of: description="In-line Formulae" end="lead"--O--(CHR) n--;--(C═O)--O--(CHR)n--;--NH--(CHR)n;--O--(C═O)--(CHR)n--;description="In-line Formulae" end="tail" description="In-line Formulae" end="lead"--(C═O)--NH--(--CHR)n--; and--(C--O)--O--CHOH--CH2--O--;description="In-line Formulae" end="tail" wherein R is hydrogen or an alkyl group selected from the group consisting of methyl, ethyl propyl and butyl groups and where n is an integer in the range from 1 to 12. 11. The composition of claim 9, wherein the polymeric backbone comprises monomers selected from the group consisting of ethylene and styrene. 12. The composition of claim 9, wherein the cyclic olefinic pendent groups are selected from the group consisting of cyclohexene-4-methylene radical, 1-methyl cyclohexene-4-methylene radical, 2-methyl cyclohexene-4-methylene radical, 5-methyl cyclohexene-4-methylene radical, 1,2-dimethyl cyclohexene-4-methylene radical, 1,5-dimethyl cyclohexene-4-methylene radical, 2,5-dimethyl cyclohexene-4-methylene radical, 1,2,5-trimethyl cyclohexene-4-methylene radical, cyclohexene-4-ethylene radical, 1-methyl cyclohexene-4-ethylene radical, 2-methyl cyclohexene-4-ethylene radical, 5-methyl cyclohexene-4-ethylene radical, 1,2-dimethyl cyclohexene-4-ethylene radical, 1,5-dimethyl cyclohexene-4-ethylene radical, 2,5-methyl cyclohexene-4-ethylene radical, 1,2,5-trimethyl cyclohexene-4-ethylene radical, cyclohexene-4-propylene radical, 1-methyl cyclohexene-4-propylene radical, 2-methyl cyclohexene-4-propylene radical, 5-methyl cyclohexene-4-propylene radical, 1,2-dimethyl cyclohexene-4-propylene radical, 1,5-dimethyl cyclohexene-4-propylene radical, 2,5-dimethyl cyclohexene-4-propylene radical, 1,2,5-trimethyl cyclohexene-4-propylene radical, cyclopenten-4-methylene radical, 1-methyl cyclopentene-4-methylene radical, 3-methyl cyclopentene-4-methylene radical, 1,2-dimethyl cyclopentene-4-methylene radical, 3,5-dimethyl cyclopentene-4-methylene radical, 1,3-dimethyl cyclopentene-4-methylene radical, 2,3-dimethyl cyclopentene-4-methylene radical, 1,2,3-trimethyl cyclopentene-4-methylene radical, 1,2,3,5-tetramethyl cyclopentene-4-methylene radical, cyclopentene-4-ethylene radical, 1-methyl cyclopentene-4-ethylene radical, 3-methyl cyclopentene-4-ethylene radical, 1,2-dimethyl cyclopentene-4-ethylene radical, 3,5-dimethyl cyclopentene-4-ethylene radical, 1,3-dimethyl cyclopentene-4-ethylene radical, 2,3-dimethyl cyclopentene-4-ethylene radical, 1,2,3-trimethyl cyclopentene-4-ethylene radical, 1,2,3, 5-tetramethyl cyclopentene-4-ethylene radical, cyclopentene-4-propylene radical, 1-methyl cyclopentene-4-propylene radical, 3-methyl cyclopentene-4-propylene radical, 1,2-dimethyl cyclopentene-4-propylene radical, 3,5-dimethyl cyclopentene-4-propylene radical, 1,3-dimethyl cyclopentene-4-propylene radical, 2,3-dimethyl cyclopentene-4-propylene radical, 1,2,3-trimethyl cyclopentene-4-propylene radical, and 1,2,3,5-tetramethyl cyclopentene-4-propylene radical. 13. The composition of claim 9, wherein the compound is an ethylene/methyl acrylate/cyclohexenyl methyl acrylate terpolymer. 14. The composition of claim 9, wherein odor and taste characteristics of products packaged with material comprised of the composition are not adulterated as a result of oxidation of the composition. 15. The composition of claim 9, wherein there is no significant fragmentation of the olefinic pendent groups and linking groups from the polymeric backbone as a result of oxidation of the composition. 16. The composition of claim 9, further comprising at least one triggering material to enhance initiation of oxygen scavenging. 17. The composition of claim 9, wherein the cyclic olefinic pendent groups are grafted onto the linking groups of the polymeric backbone by a esterification, transesterification, amidation or transamidation reaction. 18. The composition of claim 17, wherein the esterification, transesterification, amidation or transamidation reaction is a solution reaction or a reactive extrusion. 19. The composition of claim 17, wherein the esterification, transesterification, amidation or transamidation reaction is catalyzed by a catalyst selected from the group consisting of strong non-oxidizing acids, tertiary amines, Group I alkoxides, Group IVB alkoxides, and Group IVA organometallics. 20. The composition of claim 19, wherein the catalyst is selected from a group consisting of toluene sulfonic acid, sodium methoxide, tetrabutyl titanate, tetraisopropyl titanate, tetra-n-propyl-titanate, tetraethyl titanate, 2-hydroxy-pyridine and dibutyltin dilaurate. 21. The composition of claim 9, wherein the metal in the metal salt is cobalt. 22. The composition according to claim 21, wherein the metal salt is selected from the group consisting of cobalt neodecanoate, cobalt 2-ethylhexanoate, cobalt oleate and cobalt stearate. 23. The composition of claim 22, wherein the triggering material is a photo initiator. 24. An article of manufacture suitable as a container, the container inhibiting oxidation of contents of the container by removing oxygen from the container and by inhibiting ingress of oxygen into the container from outside the container, wherein the article comprises an oxygen scavenging composition which comprises: (a) a compound comprising a polymeric backbone, cyclic olefinic pendant groups, and linking groups linking the olefinic pendant groups to the backbone, and comprising the formula (II) as follows: wherein P+T+Q is 100 mol % of the compound; P, T, and Q are each greater than 0 mol % of the compound; Z is selected from the group consisting of an aryl group;--(C═O)OR1;--O(C═O)R 1; and an alkyl aryl group: where R4 is selected from the group consisting of--CH3, ethyl, and hydrogen; R1 is selected from the group consisting of hydrogen, methyl, ethyl,--C3H7 and--C4H9; R2 and R3 are selected from the group consisting of hydrogen and methyl; X is selected from the group consisting of--O--,--NH--,--(C═O)O--,--(C═O)NH--,--(C═ O)S--,--O(C═O)--and--(CHR)1, L is an integer in the range from 1 to 6; Y is--(CHR)n--, where n is an integer in the range from 0 to 12, R being selected from the group consisting of hydrogen, methyl and ethyl; where q1, q2, q3, q4, and r are selected from the group consisting of hydrogen, methyl, and ethyl; and where m is--(CH2)n--and where n is an integer in the range from 0 to 4; and wherein when r is hydrogen, at least one of q1, q2, q3 and q4 is hydrogen; and (b) a transition metal catalyst. 25. The article of manufacture of claim 24, wherein the polymeric backbone is ethylenic and the linking groups are selected from the group consisting of: description="In-line Formulae" end="lead"--O--(CHR) n--;--(C═O)--O--(CHR)n--;--NH--(CHR)n--;--O--(C═O)--(CHR)n--;description="In-line Formulae" end="tail" description="In-line Formulae" end="lead"--(C═O)--NH--(--CHR)n--; and--(C═O)--O--CHOH--CH2--O--; description="In-line Formulae" end="tail" wherein R is hydrogen or an alkyl group selected from the group consisting of methyl, ethyl propyl and butyl groups and where n is an integer in the range from 1 to 12. 26. The article of manufacture of claim 24, wherein the polymeric backbone comprises monomers selected from the group consisting of ethylene and styrene. 27. The article of manufacture of claim 19, wherein the cyclic olefinic pendent groups are selected from the group consisting of cyclohexene-4-methylene radical, 1-methyl cyclohexene-4-methylene radical, 2-methyl cyclohexene-4-methylene radical, 5-methyl cyclohexene-4-methylene radical, 1,2-dimethyl cyclohexene-4-methylene radical, 1,5-dimethyl cyclohexene-4-methylene radical, 2,5-dimethyl cyclohexene-4-methylene radical, 1,2,5-trimethyl cyclohexene-4-methylene radical, cyclohexene-4-ethylene radical, 1-methyl cyclohexene-4-ethylene radical, 2-methyl cyclohexene-4-ethylene radical, 5-methyl cyclohexene-4-ethylene radical, 1,2-dimethyl cyclohexene-4-ethylene radical, 1,5-dimethyl cyclohexene-4-ethylene radical, 2,5-dimethyl cyclohexene-4-ethylene radical, 1,2,5-trimethyl cyclohexene-4-ethylene radical, cyclohexene-4-propylene radical, 1-methyl cyclohexene-4-propylene radical, 2-methyl cyclohexene-4-propylene radical, 5-methyl cyclohexene-4-propylene radical, 1,2-dimethyl cyclohexene-4-propylene radical, 1,5-dimethyl cyclohexene-4-propylene radical, 2,5-dimethyl cyclohexene-4-propylene radical, 1,2,5-trimethyl cyclohexene-4-propylene radical, cyclopentene-4-methylene radical, 1-methyl cyclopentene-4-methylene radical 3-methyl cyclopentene-4-methylene radical, 1,2-dimethyl cyclopentene-4-methylene radical, 3,5-dimethyl cyclopentene-4-methylene radical, 1,3-dimethyl cyclopentene-4-methylene radical, 2,3-dimethyl cyclopentene-4-methylene radical, 1,2,3-trimethyl cyclopentene-4-methylene radical, 1,2,3,5-tetramethyl cyclopentene-4-methylene radical, cyclopentene-4-ethylene radical, 1-methyl cyclopentene-4-ethylene radical, 3-methyl cyclopentene-4-ethylene radical, 1,2-dimethyl cyclopentene-4-ethylene radical, 3-dimethyl cyclopentene-4-ethylene radical, 1,3-dimethyl cyclopentene-4-ethylene radical, 2,3-dimethyl cyclopentene-4-ethylene radical, 1,2,3-trimethyl cyclopentene-4-ethylene radical, 1,2,3,5-tetramethyl cyclopentene-4-ethylene radical, cyclopentene-4-propylene radical, 1-methyl cyclopentene-4-propylene radical, 3-methyl cyclopentene-4-propylene radical, 1,2-dimethyl cyclopentene-4-propylene radical, 3,5-dimethyl cyclopentene-4-propylene radical, 1,3-dimethyl cyclopentene-4-propylene radical, 2,3-dimethyl cyclopentene-4-propylene radical, 1,2,3-trimethyl cyclopentene-4-propylene radical, and 1,2,3,5-tetramethyl cyclopentene-4-propylene radical. 28. The article of manufacture of claim 19, wherein the compound is an ethylene/methyl acrylate/cyclohexenyl methyl acrylate terpolymer. 29. The article of manufacture of claim 24, wherein odor and taste characteristics of products packaged with material comprised of the composition are not adulterated as a result of oxidation of the composition. 30. The article of manufacture of claim 24, wherein there is no significant fragmentation of the olefinic pendent groups and linking groups from the polymeric backbone as a result of oxidation of the composition. 31. The article of manufacture of claim 24, wherein the cyclic olefinic pendent groups are grafted onto the linking groups of the polymeric backbone by a esterification, transesterification, amidation or transamidation reaction. 32. Previously presented) The article of manufacture of claim 31, wherein the esterification, transesterification, amidation or transamidation reaction is a solution reaction or a reactive extrusion. 33. The article of manufacture of claim 31, wherein the esterification, transesterification, amidation or transamidation reaction is catalyzed by a catalyst selected from the group consisting of strong non-oxidizing acids, tertiary amines, Group I alkoxides, Group IVB alkoxides, and Group IVA organometallics. 34. The article of manufacture of claim 33, wherein the catalyst is selected from the group consisting of toluene sulfonic acid, sodium methoxide, tetrabutyl titanate, tetraisopropyl titanate, tetra-n-propyl-titanate, tetraethyl titanate, 2-hydroxy-pyridine and dibutyltin dilaurate. 35. The article of manufacture according to claim 24, wherein the transition metal catalyst is a metal salt. 36. The article of manufacture according to claim 35, wherein the metal in the metal salt is cobalt. 37. The article of manufacture of according to claim 36, wherein the metal salt is selected from the group consisting of cobalt neodecanoate, cobalt 2-ethylhexanoate, cobalt oleate and cobalt stearate. 38. The article of manufacture of claim 24, further comprising at least one triggering material to enhance initiation of oxygen scavenging. 39. The article of manufacture of claim 38, wherein the triggering material is a photoinitiator. 40. The article of manufacture of claim 24 wherein the article is a package. 41. The article of manufacture of claim 40, wherein the package comprises a flexible film having a thickness of at most 10 mil or a flexible sheet having a thickness of at least 10 mil. 42. The article of manufacture of claim 40, wherein the article is a package with a food product located within the package. 43. The article of manufacture of claim 40, wherein the article is a package for packaging a cosmetic, chemical, electronic device, pesticide or a pharmaceutical composition. 44. A multi-layer film comprising the article of manufacture according to claim 24, and at least one additional functional layer. 45. The multi-layer film according to claim 44, wherein at least one additional layer is selected from among oxygen barrier layers, polymeric selective barrier layers, structural layers and heat seal layers. 46. The multi-layer film according to claim 44, wherein the at least one additional layer is an oxygen barrier layer. 47. The multi-layer film according to claim 46, further comprising at least one polymeric selective barrier layer. 48. The multi-layer film according to claim 46, further comprising at least one heat seal layer. 49. The multi-layer film according to claim 46, further comprising at least one structural layer. 50. The article of claim 24, wherein the article is a rigid container, sealing gasket, patch, container closure device, bottle cap, bottle cap insert or molded or thermoformed shape. 51. The article of claim 50, wherein the molded or thermoformed shape is a bottle or tray. 52. A layer suitable for scavenging oxygen, comprising: (a) a compound comprising a polymeric backbone, cyclic olefinic pendent groups and linking groups linking the olefinic pendent groups to the polymeric backbone, and comprising the formula (II) as follows: wherein P+T+Q is 100 mol % of the compound; P, T, and Q are each greater than 0 mol % of the compound; Z is selected from the group consisting of an aryl group;--(C═O)OR1;--O(C═O)R 1; and an all aryl group; where R4 is selected from the group consisting of--CH3, ethyl, and hydrogen; R1 is selected from the group consisting of hydrogen, methyl, ethyl,--C3H7 and--C4H9; R2 and R3 are selected from the group consisting of hydrogen and methyl; X is selected from the group consisting of--O--,--NH--,--(C═O)O--,--(C═O)NH--,--(C--O)S--,--O(C═O)--and--(CHR)L--; L is an integer in the range from 1 to 6; Y is--(CHR)n--, where n is an integer in the range from 0 to 12, R being selected from the group consisting of hydrogen, methyl and ethyl; where q1, q2, q3, q4 , and r are selected from the group consisting of hydrogen, methyl, and ethyl; and where m is--(CH2)n--and where n is an integer in the range from 0 to 4; and wherein when r is hydrogen, at least one of q1, q2, q3 and q4 is hydrogen; and (b) a transition metal catalyst. 53. The layer of claim 52, wherein odor and taste characteristics of products packaged with material comprised of the layer are not adulterated as a result of oxidation of the layer. 54. The layer of claim 52, wherein there is no significant fragmentation of the olefinic pendent groups and linking groups from the polymeric backbone as a result of oxidation of the layer. 55. An article for packaging wherein the article comprises a layer according to claim 52. 56. A layer according to claim 52, wherein the transition metal catalyst is a metal salt. 57. A layer according to claim 56, wherein the transition metal in the metal salt is cobalt. 58. A layer according to claim 56, wherein the metal salt selected from the group consisting of cobalt neodecanoate, cobalt 2-ethylhexanoate, cobalt oleate and cobalt stearate. 59. A layer according to claim 52, wherein said layer in addition comprises polymeric diluent. 60. A layer according to claim 59, wherein said diluent is a thermoplastic polymer. 61. A layer according to claim 52, wherein said layer is adjacent to one or more additional layers. 62. A layer according to claim 61, wherein at least one additional layer is an oxygen barrier. 63. A layer according to claim 62, wherein said oxygen barrier comprises at least one material selected from the group consisting of poly(ethylene-vinyl alcohol), polyacrylonitrile, poly(vinyl chloride), polyamides, poly(vinylidene dichloride), poly(ethylene terephthalate), silica, metal foil and metalized polymeric films. 64. Previously presented) A layer according to claim 61, wherein one or more of said additional layer or layers is coextruded with said layer. 65. A layer according to claim 61, wherein one or more of said additional layer or layers is laminated onto said layer. 66. A layer according to claim 61, wherein one or more of said additional layer or layers is coated onto said layer. 67. A layer according to claim 61, wherein said layer is flexible. 68. A layer according to claim 61, wherein said layer is transparent. 69. A process of making a polymer material by a process comprising transesterification of an ethylene copolymer with an alcohol comprising a cyclic olefinic group, wherein the polymer material that is produced comprises a polymer backbone, cyclic olefinic pendant groups, and linking groups linking the backbone with the pendant groups; and comprising the formula (II) as follows: wherein P+T+Q is 100 mol % of the compound; P, T, and Q are each greater than 0 mol % of the compound; Z is selected from the group consisting of an aryl group;--(C═O)OR1;--O(C═O)R 1; and an alkyl aryl group: where R4 is selected from the group consisting of--CH3, ethyl, and hydrogen; R1 is selected from the group consisting of hydrogen, methyl, ethyl,--C3H7 and--C4H9; R2 and R3 are selected from the group consisting of hydrogen and methyl; X is selected from the group consisting of--O--,--NH--,--(C═O)O--,--(C═O)NH--,--(C--O)S--,--O(C═O)--and--(CHR)L--; L is an integer in the range from 1 to 6; Y is--(CHR)n--, where n is an integer in the range from 0 to 12, R being selected from the group consisting of hydrogen, methyl and ethyl; where q1, q2, q3, q4 , and r are selected from the group consisting of hydrogen, methyl, and ethyl; and where m is--(CH2)n--and where n is an integer in the range from 0 to 4; and wherein when r is hydrogen, at least one of q1, q2, q3 and q4 is hydrogen. 70. The process of claim 69, wherein the reaction is a solution reaction or a reactive extrusion. 71. The process of claim 69, wherein the process comprises the steps of: (a) selecting at least one polymer from the group consisting of ethylene/maleic anhydride, ethylene/acrylic acid, ethylene/methacrylic acid, ethylene/methyl acrylate, ethylene/ethyl acrylate, and ethylene/butyl acrylate, and at least one transesterifying compound selected from the group consisting of cyclohexene-4-methanol, 1-methyl cyclohexene-4-methanol, 2-methyl cyclohexene-4-methanol, 5-methyl cyclohexene-4-methanol, 1,2-dimethyl cyclohexene-4-methanol, 1,5-dimethyl cyclohexene-4-methanol, 2,5-dimethyl cyclohexene-4-methanol, 1,2,5-trimethyl cyclohexene-4-methanol, cyclohexene-4-ethanol, 1-methyl cyclohexene-4-ethanol, 2-methyl cyclohexene-4-ethanol, 5-methyl cyclohexene-4-ethanol, 1,2-dimethyl cyclohexene-4-ethanol, 1,5-dimethyl cyclohexene-4-ethanol, 2,5-dimethyl cyclohexene-4-ethanol, 1,2,5-trimethyl cyclohexene-4-ethanol, cyclohexene-4-propanol, 1-methyl cyclohexene-4-propanol, 2-methyl cyclohexene-4-propanol, 5-methyl cyclohexene-4-propanol, 1,2-dimethyl cyclohexene-4-propanol, 1,5-dimethyl cyclohexene-4-propanol, 2,5-dimethyl cyclohexene-4-propanol, 1,2,5-trimethyl cyclohexene-4-propanol, cyclopentene-4-methanol, 1-methyl cyclopentene-4-methanol, 3-methyl cyclopentene-4-methanol, 1,2-dimethyl cyclopentene-4-methanol, 3,5-dimethyl cyclopentene-4-methanol, 1,3-dimethyl cyclopentene-4-methanol, 2,3-dimethyl cyclopentene-4-methanol, 1, 2,3-trimethyl cyclopentene-4-methanol, 1,2,3,5-tetramethyl cyclopentene-4-methanol, cyclopentene ethanol, 1-methyl cyclopentene-4-ethanol, 3-methyl cyclopentene-4-ethanol, 1,2-dimethyl cyclopentene-4-ethanol, 3,5-dimethyl cyclopentene-4-ethanol, 1,3-dimethyl cyclopentene-4-ethanol, 2,3-dimethyl cyclopentene-4-ethanol, 1,2,3-trimethyl cyclopentene-4-ethanol, 1,2,3,5-tetramethyl cyclopentene-4-ethanol, cyclopentene-4-propanol, 1-methyl cyclopentene-4-propanol, 3-methyl cyclopentene-4-propanol, 1,2-dimethyl cyclopentene-4-propanol, 3,5-dimethyl cyclopentene-4-propanol, 1,3-dimethyl cyclopentene-4-propanol, 2,3-dimethyl cyclopentene-4-propanol, 1, 2,3-trimethyl cyclopentene-4-propanol, and 1,2,3,5-tetramethyl cyclopentene-4-propanol, and combining the at least one polymer and the at least one transesterifying compound; (b) heating the polymer and transesterifying compound selected in (a) to form a polymer melt; (c) processing the melt in an extruder under transesterification conditions with transesterification catalysts and antioxidants protecting the melt from oxidation during extrusion, so that the polymer melt undergoes exchange of alkyl groups of polymeric esters with cyclic olefin pendent groups; and (d) removing volatile organic products and by-products from the melt. 72. The process of claim 71, wherein the polymeric backbone is ethylenic and the linking groups are selected from the group consisting of: description="In-line Formulae" end="lead"--O--(CHR) n--;--(C═O)--O--(CHR)n--;--NH--(CHR)n--; description="In-line Formulae" end="tail" description="In-line Formulae" end="lead"--O--(C═O)--(CHR)n--;--(C═O)--NH--(--CHR)n--; and--(C--O)--O--CHOH--CH2--O--;description="In-line Formulae" end="tail" where R is hydrogen or an alkyl group selected from the group consisting of methyl, ethyl, propyl and butyl groups and where n is an integer in the range from 1 to 12. 73. The process of claim 71, wherein the polymeric backbone is ethylenic backbone and the linking group is: description="In-line Formulae" end="lead"--(C═O)--NH--(CHR)n description="In-line Formulae" end="tail" where R is hydrogen or an alkyl group selected from the group consisting of methyl, ethyl, propyl and butyl groups and where n is an integer in the range from 1 to 12. 74. The process of claim 69, further comprising adding to the polymer material a transition metal catalyst. 75. The process of claim 74, wherein the transition metal catalyst is a metal salt. 76. The process of claim 75, wherein the metal in the metal salt is cobalt. 77. The process of claim 75, wherein the metal salt is selected from the group consisting of cobalt neodecanoate, cobalt 2-ethylhexanoate, cobalt oleate and cobalt stearate. 78. Previously presented) The process of claim 69, further comprising adding to the polymer material at least one triggering material to enhance initiation of oxygen scavenging. 79. The process of claim 78, wherein the triggering material is a photoinitiator. 80. The process of claim 69, wherein the transesterification reaction is catalyzed by a catalyst selected from the group consisting of strong non-oxidizing acids, tertiary amines, Group I alkoxides, Group IVB alkoxides, Group IVA organometallics. 81. The process of claim 80, wherein the catalyst is selected from the group consisting of toluene sulfonic acid, sodium methoxide, tetrabutyl titanate, tetraisopropyl titanate, tetra-n-propyl-titanate, tetraethyl titanate, 2-hydroxy-pyridine and dibutyltin dilaurate. 82. The process of claim 69, wherein the cyclic olefinic pendent groups are selected from the group consisting of cyclohexene-4-methylene radical, 1-methyl cyclohexene-4-methylene radical, 2-methyl cyclohexene-4-methylene radical, 5-methyl cyclohexene-4-methylene radical, 1,2-dimethyl cyclohexene-4-methylene radical, 1,5-dimethyl cyclohexene-4-methylene radical, 2,5-dimethyl cyclohexene-4-methylene radical, 1,2,5-trimethyl cyclohexene-4-methylene radical, cyclohexene-4-ethylene radical, 1-methyl cyclohexene-4-ethylene radical, 2-methyl cyclohexene-4-ethylene radical, 5-methyl cyclohexene-4-ethylene radical, 1,2-dimethyl cyclohexene-4-ethylene radical, 1,5-methyl cyclohexene-4-ethylene radical 2,5-dimethyl cyclohexene-4-ethylene radical, 1,2,5-trimethyl cyclohexene-4-ethylene radical, cyclohexene-4-propylene radical, 1-methyl cyclohexene-4-propylene radical, 2-methyl cyclohexene-4-propylene radical, 5-methyl cyclohexene-4-propylene radical, 1,2-dimethyl cyclohexene-4-propylene radical, 1,5-dimethyl cyclohexene-4-propylene radical, 2,5-dimethyl cyclohexene-4-propylene radical, 1,2,5-trimethyl cyclohexene-4-propylene radical, cyclopentene-4-methylene radical, 1-methyl cyclopentene-4-methylene radical, 3-methyl cyclopentene-4-methylene radical, 1,2-dimethyl cyclopentene-4-methylene radical, 3,5-dimethyl cyclopentene-4-methylene radical, 1,3-dimethyl cyclopentene-4-methylene radical, 2,3-dimethyl cyclopentene-4-methylene radical, 1,2,3-trimethyl cyclopentene-4-methylene radical, 1,2,3,5-tetramethyl cyclopentene-4-methylene radical, cyclopentene-4-ethylene radical, 1-methyl cyclopentene-4-ethylene radical, 3-methyl cyclopentene-4-ethylene radical, 1,2-dimethyl cyclopentene-4-ethylene radical, 3,5-dimethyl cyclopentene-4-ethylene radical, 1,3-dimethyl cyclopentene-4-ethylene radical, 2,3-dimethyl cyclopentene-4-ethylene radical, 1,2,3-trimethyl cyclopentene-4-ethylene radical, 1,2,3, 5-tetramethyl cyclopentene-4-ethylene radical, cyclopentene-4-propylene radical, 1-methyl cyclopentene-4-propylene radical, 3-methyl cyclopentene-4-propylene radical, 1,2-dimethyl cyclopentene-4-propylene radical, 3,5-dimethyl cyclopentene-4-propylene radical, 1,3-dimethyl cyclopentene-4-propylene radical, 2,3-dimethyl cyclopentene-4-propylene radical, 1,2,3-trimethyl cyclopentene-4-propylene radical, and 1,2,3,5-tetramethyl cyclopentene-4-propylene radical. 83. The process of claim 82, wherein the polymer is a ethylene/methyl acrylate/cyclohexenyl methyl acrylate terpolymer.
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이 특허에 인용된 특허 (29)
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