Grafted cyclodextrin

• US 7,365,123 B2
• Filed: 04/13/2006
• Issued: 04/29/2008
• Est. Priority Date: 12/10/2002
• Status: Expired due to Term

• Current Assignee: Verdant Technologies, Inc.
• Original Assignee: Cellresin Technologies, LLC
• Inventors: Wood, Willard E., Beaverson, Neil J., Seethamraju, Kasyap V.
• Primary Examiner(s): Gulakowski; Randy
• Assistant Examiner(s): Asinovsky; Olga
• Application Number:
  US11/403,446
• Publication Number:
  US 20060183856A1
• Time in Patent Office: 747 Days
• Field of Search: 525/54.2, 525/64, 525/207, 525/187, 525/285, 428/34.1, 428/35.7, 428/36.92, 428/355.EN, 428/339, 524/48
• US Class Current: 525/54.2
• 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 method of manufacturing a barrier material comprising the steps of:

(a) combining a polymer and a modified polymer, the modified polymer comprising a cyclodextrin bonded to a backbone of the polymer through a maleic anhydride residue or to a carbon in a pendent group through a maleic anhydride residue;

wherein the cyclodextrin compound is substantially free of the compound in central core of the cyclodextrin ring; and

(b) extruding the polymer and modified polymer to form a barrier composition comprising about 0.01 to 10 wt % of the modified polymer.

2. A method comprising grafting a parent, umodified cyclodextrin onto a polyolefin using extrusion processing.

3. A method of claim 2, wherein extruding and grafting the polymer occurs in one-step.

4. A method of claim 3, wherein extruding and grafting the polymer occurs simultaneously.

5. A method of claim 2, wherein the grafting comprises a hydroxyl group of the cyclodextrin reacts with a functional group on the polyolefin.

6. A method of claim 5, wherein the hydroxyl group of the cyclodextrin reacts with an anhydride moiety on the polyolefin.

7. A method of claim 6, wherein the hydroxyl group of the cyclodextrin reacts with a maleic anhydride moiety on the polyolefin.

8. A method of claim 5, wherein the hydroxyl group of the cyclodextrin reacts with an epoxide moiety on the polyolefin.

9. A method of claim 2, wherein the grafting is melt grafting.

10. A method of claim 2, wherein the polyolefin is poly(ethylene), poly(propylene), poly(ethylene-co-propylene), ethylene/methyl acrylate copolymer, or ethylene/ethyl acrylate copolymer.

11. A method of claim 3, wherein the polyolefin is poly(ethylene), poly(propylene), poly(ethylene-co-propylene), ethylene/methyl acrylate copolymer, or ethylene/ethyl acrylate copolymer.

12. A method of claim 4, wherein the polyolefin is poly(ethylene), poly(propylene), poly(ethylene-co-propylene), ethylene/methyl acrylate copolymer, or ethylene/ethyl acrylate copolymer.

13. A method of claim 5, wherein the polyolefin is poly(ethylene), poly(propylene), poly(ethylene-co-propylene), ethylene/methyl acrylate copolymer, or ethylene/ethyl acrylate copolymer.

14. A method of claim 6, wherein the polyolefin is poly(ethylene), poly(propylene), poly(ethylene-co-propylene), ethylene/methyl acrylate copolymer, or ethylene/ethyl acrylate copolymer.

15. A method of claim 7, wherein the polyolefin is poly(ethylene), poly(propylene), poly(ethylene-co-propylene), ethylene/methyl acrylate copolymer, or ethylene/ethyl acrylate copolymer.

16. A method of claim 8, wherein the polyolefin is poly(ethylene), poly(propylene), poly(ethylene-co-propylene), ethylene/methyl acrylate copolymer, or ethylene/ethyl acrylate copolymer.