Grafted cyclodextrin

• US 20060182917A1
• Filed: 04/13/2006
• Published: 08/17/2006
• Est. Priority Date: 12/10/2002
• Status: Active Grant

• Current Assignee: Verdant Technologies, Inc.
• Original Assignee: Cellresin Technologies, LLC
• Inventors: Wood, Willard E., Beaverson, Neil J., Seethamraju, Kasyap V.
• Granted Patent: US 8,501,308 B2
• Time in Patent Office: Days
• US Class Current: 428/36.910
• CPC Class Codes: B32B 27/02 in the form of fibres or filaments not used
• CPC Class Codes: B32B 27/28 comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
• CPC Class Codes: B32B 27/32 comprising polyolefins comprising vinyl (co)polymers or acrylic (co)polymers B32B27/30
• CPC Class Codes: C08B 37/0012 Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
• CPC Class Codes: C08L 23/04 Homopolymers or copolymers of ethene
• CPC Class Codes: C08L 2666/24 Graft or block copolymers according to groups C08L51/00, C08L53/00 or C08L55/02; Derivatives thereof
• CPC Class Codes: C08L 5/16 Cyclodextrin; Derivatives thereof
• CPC Class Codes: C08L 51/06 grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
• CPC Class Codes: Y10T 428/13 Hollow or container type article [e.g., tube, vase, etc.]
• CPC Class Codes: Y10T 428/1352 Polymer or resin containing [i.e., natural or synthetic]
• CPC Class Codes: Y10T 428/1393 Multilayer [continuous layer]
• CPC Class Codes: Y10T 428/1397 Single layer [continuous layer]
• CPC Class Codes: Y10T 428/249926 Including paper layer
• CPC Class Codes: Y10T 428/24998 Composite has more than two layers
• CPC Class Codes: Y10T 428/269 including synthetic resin or polymer layer or component
• CPC Class Codes: Y10T 428/2878 including addition polymer from unsaturated monomer
• CPC Class Codes: Y10T 428/2929 Bicomponent, conjugate, composite or collateral fibers or filaments [i.e., coextruded sheath-core or side-by-side type]
• CPC Class Codes: Y10T 428/298 Physical dimension
• CPC Class Codes: Y10T 428/31895 Paper or wood
• CPC Class Codes: Y10T 428/31902 Monoethylenically unsaturated

Abstract

Thermoplastic polymer compositions, films, continues, closures, laminates can comprise a modified vinyl polymer said modified polymer having a moiety comprising a cyclodextrin compound. The cyclodextrin compound, locked into the polymer structure, can absorb impurities, permeants, or other undesirable volatile materials. The cooperation between the cyclodextrin grafted onto the thermoplastic polymer and the polymer structure can provide barrier properties to a film, web or other polymer structure. A permeant or a contaminant can be complexed or trapped within the polymer and held within the film or Web preventing the permeant or contaminant from passing into the interior of a container or enclosure.

Claims

1. A container comprising an enclosed volume surrounded by a polyolefin web, the web comprising a blend of a polyolefin resin and a modified polyolefin resin, the modified polyolefin resin comprising a polymethylene backbone having randomly substituted covalently bonded groups derived from a cyclodextrin compound, the chip comprising about 100 parts by weight of the polyolefin resin and about 0.01 to 10 parts by weight of the modified polyolefin;

wherein the cyclodextrin compound is substantially free of a compound in the central pore of the cyclodextrin ring.

2. The container of claim 1 wherein the web comprises a laminate comprising a paperboard layer and a bonded polyolefin layer

3. The container of claim 1 wherein the web is filled with a liquid food.

4. The container of claim 3 wherein web has a capacity of about 100 mL to 3 liters and the liquid food comprises a citrus juice.

5. The container of claim 1 wherein the polyolefin comprises a polyolefin having a melt index of about 0.5 to 100 g-10 min.⁻

1

6. The container of claim 1 wherein the polyolefin comprises a polyolefin having a melt index of about 0.7 to 200 g-10 min.⁻

1

7. The container of claim 1 wherein the polyolefin comprises a polyethylene.

8. The container of claim 1 wherein the modified polyolefin comprises a modified polyethylene.

9. The container of claim 1 wherein the polyolefin comprises a polypropylene.

10. The container of claim 1 wherein the modified polyolefin comprises a modified polypropylene.

11. The container of claim 1 wherein the polyolefin comprises a poly(ethylene-co-propylene).

12. The container of claim 1 wherein the modified polyolefin comprises a modified poly(ethylene-co-propylene).

13. The container of claim 1 wherein the modified polyolefin comprises a cyclodextrin bonded to a maleic acid modified polyolefin wherein the polyolefin comprises about 0.05 to 2 weight percent maleic anhydride.

14. The container of claim 1 wherein the modified polyolefin comprises a cyclodextrin bonded to a maleic acid modified polyolefin wherein the polyolefin comprises about 0.1 to 1 weight percent maleic anhydride.

15. The chip of claim 7 wherein the polyethylene comprises a low-density polyethylene.

16. The chip of claim 7 wherein the polyethylene comprises a linear low-density polyethylene.

17. The chip of claim 7 wherein the polyethylene comprises a high-density polyethylene.

18. A film comprising a blend of a polyolefin resin and a modified polyolefin resin, the modified polyolefin resin comprising a polymethylene backbone having randomly substituted groups derived from a cyclodextrin compound, the film comprising about 100 parts by weight of the polyolefin resin and about 0.01 to 10 parts by weight of the modified polyolefin;

wherein the cyclodextrin compound is substantially free of a compound in the central pore of the cyclodextrin ring.

19. The film of claim 18 wherein the film comprises a laminate comprising a paperboard layer and a polyolefin layer.

20. The film of claim 18 wherein the polyolefin comprises a melt index of about 0.5 to 100 g-10 min.⁻

1

21. The film of claim 18 wherein the polyolefin comprises a melt index of about 0.7 to 200 g-10 min.⁻

1

22. The film of claim 18 wherein the polyolefin comprises a polyethylene.

23. The film of claim 18 wherein the modified polyolefin comprises a modified polyethylene.

24. The film of claim 18 wherein the polyolefin comprises a polypropylene.

25. The film of claim 18 wherein the modified polyolefin comprises a modified polypropylene.

26. The film of claim 18 wherein the polyolefin comprises a poly(ethylene-co-propylene).

27. The film of claim 18 wherein the modified polyolefin comprises a modified poly(ethylene-co-propylene).

28. The film of claim 18 wherein the cyclodextrin compound has a substituent substantially on at least one —

OH group at the -2, -3 or the -6 position of the glucose moiety in the cyclodextrin.

29. The film of claim 18 wherein the modified polyolefin comprises a cyclodextrin bonded to a maleic acid modified polyolefin wherein the polyolefin comprises about 0.05 to 5 weight percent maleic anhydride.

30. The film of claim 18 wherein the modified polyolefin comprises a cyclodextrin bonded to a maleic acid modified polyolefin wherein the polyolefin comprises about 0.1 to 2 weight percent maleic anhydride.

31. The film of claim 22 wherein the polyethylene comprises a low-density polyethylene.

32. The film of claim 22 wherein the polyethylene comprises a linear low-density polyethylene.

33. The film of claim 22 wherein the polyethylene comprises a high-density polyethylene.

34. A bottle cap comprising an enclosed volume surrounded by a polyolefin web, the web comprising a blend of a polyolefin resin and a modified polyolefin resin, the modified polyolefin resin comprising a polymethylene backbone having randomly substituted covalently bonded groups derived from a cyclodextrin compound, the chip comprising about 100 parts by weight of the polyolefin resin and about 0.01 to 10 parts by weight of the modified polyolefin per part by weight of the resin;

wherein the cyclodextrin compound is substantially free of a compound in the central pore of the cyclodextrin ring.

35. The bottle cap of claim 34, wherein the web comprises a cap liner laminate comprising a paperboard layer bonded to polyolefin layer.

36. The bottle cap of claim 34, wherein threads along inner surface of the bottle cap mate with threads along the top, external surface of the bottle.

37. The bottle cap of claim 34, wherein side walls extend from the bottom suface of said bottle cap and form a substantially cylindrical cavity.

38. The bottle cap of claim 34 wherein the polyolefin comprises a polyolefin having a melt index of about 0.5 to 100 g-10 min.⁻

1

39. The bottle cap of claim 34 wherein the polyolefin comprises a polyolefin having a melt index of about 0.7 to 200 g-10 min.⁻

1

40. The bottle cap of claim 34 wherein the polyolefin comprises a polyethylene.

41. The bottle cap of claim 34 wherein the modified polyolefin comprises a modified polyethylene.

42. The bottle cap of claim 34 wherein the polyolefin comprises a polypropylene.

43. The bottle cap of claim 34 wherein the modified polyolefin comprises a modified polypropylene.

44. The bottle cap of claim 34 wherein the polyolefin comprises a poly(ethylene-co-propylene).

45. The bottle cap of claim 34 wherein the modified polyolefin comprises a modified poly(ethylene-co-propylene).

46. The bottle cap of claim 34 wherein the modified polyolefin comprises a cyclodextrin bonded to a maleic acid modified polyolefin wherein the polyolefin comprises about 0.02 to 2 weight percent maleic anhydride.

47. The bottle cap of claim 34 wherein the modified polyolefin comprises a cyclodextrin bonded to a maleic acid modified polyolefin wherein the polyolefin comprises about 0.02 to 1 weight percent maleic anhydride.

48. The bottle cap of claim 40 wherein the polyethylene comprises a low-density polyethylene.

49. The bottle cap of claim 40 wherein the polyethylene comprises a linear low-density polyethylene.

50. The bottle cap of claim 40 wherein the polyethylene comprises a high-density polyethylene.

51. A bottle cap liner comprising an enclosed volume surrounded by a polyolefin web, the web comprising a blend of a polyolefin resin and a modified polyolefin resin, the modified polyolefin resin comprising a polymethylene backbone having randomly substituted covalently bonded groups derived from a cyclodextrin compound, the chip comprising about 100 parts by weight of the polyolefin resin and about 0.01 to 10 parts by weight of the modified polyolefin;

wherein the cyclodextrin compound is substantially free of a compound in the central pore of the cyclodextrin ring.

52. The bottle cap liner of claim 51 wherein the web comprises a laminate comprising a paperboard layer and a bonded polyolefin layer.

53. The bottle cap liner of claim 51 wherein the polyolefin comprises a polyolefin having a melt index of about 0.5 to 100 g-10 min.⁻

1

54. The bottle cap liner of claim 51 wherein the polyolefin comprises a polyolefin having a melt index of about 0.7 to 200 g-10 min.⁻

1

55. The bottle cap liner of claim 51 wherein the polyolefin comprises a polyethylene.

56. The bottle cap liner of claim 51 wherein the modified polyolefin comprises a modified polyethylene.

57. The bottle cap liner of claim 51 wherein the polyolefin comprises a polypropylene.

58. The bottle cap liner of claim 51 wherein the modified polyolefin comprises a modified polypropylene.

59. The bottle cap liner of claim 51 wherein the polyolefin comprises a poly(ethylene-co-propylene).

60. The bottle cap liner of claim 51 wherein the modified polyolefin comprises a modified poly(ethylene-co-propylene).

61. The bottle cap liner of claim 51 wherein the modified polyolefin comprises a cyclodextrin bonded to a maleic acid modified polyolefin wherein the polyolefin comprises about 0.02 to 2 weight percent maleic anhydride.

62. The bottle cap liner of claim 51 wherein the modified polyolefin comprises a cyclodextrin bonded to a maleic acid modified polyolefin wherein the polyolefin comprises about 0.02 to 1 weight percent maleic anhydride.

63. The bottle cap liner of claim 55 wherein the polyethylene comprises a low-density polyethylene.

64. The bottle cap liner of claim 55 wherein the polyethylene comprises a linear low-density polyethylene.

65. The bottle cap liner of claim 55 wherein the polyethylene comprises a high-density polyethylene.