Grafted cyclodextrin

• US 7,795,333 B2
• Filed: 04/13/2006
• Issued: 09/14/2010
• Est. Priority Date: 12/10/2002
• Status: Active Grant

• Current Assignee: Verdant Technologies, Inc.
• Original Assignee: Cellresin Technologies, LLC
• Inventors: Seethamraju, Kasyap V., Wood, Willard E., Beaverson, Neil J.
• Primary Examiner(s): Nutter; Nathan M
• Application Number:
  US11/403,480
• Publication Number:
  US 20060183857A1
• Time in Patent Office: 1,615 Days
• Field of Search: 524/48, 525/54.21, 525/285
• US Class Current: 524/48
• 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 thermoplastic polymer composition, comprising a modified polyethylene, polypropylene or a poly(ethylene-co-propylene) resin comprising a polymethylene backbone comprising randomly substituted covalently bonded groups comprising a cyclodextrin compound;

wherein an hydroxyl group of the cyclodextrin is bonded to the modified resin, and the cyclodextrin compound is substantially free of an inclusion compound in the central pore of the cyclodextrin ring.

2. The thermoplastic polymer composition of claim 1 wherein the modified polyethylene, polypropylene or a poly(ethylene-co-propylene) resin is derived from a polyethylene, polypropylene or a poly(ethylene-co-propylene) having a melt index of about 0,7 to 200 g-10 min.⁻

1

3. The thermoplastic polymer composition of claim 1 wherein the modified polyethylene, polypropylene or a poly(ethylene-co-propylene) resin comprises a maleic anhydride modified polyolefin wherein the maleic anhydride modified polyolefin comprises about 0.05 to 5 weight percent maleic anhydride and wherein the modified polyethylene, polypropylene or a polyethylene-co-propylene) resin comprises a melt index of about 1 to 75 g-10 min.⁻

1 and is derived from a polyolefin having a melt index of about 1 to 100 g-10 min.<sup>−

1</sup>

4. The thermoplastic polymer composition of claim 1 wherein the modified resin comprises a cyclodextrin bonded to a maleic anhydride modified polyolefin resin, and wherein the modified polyethylene, polypropylene or a poly(ethylene-co-propylene) resin comprises about 0.1 to 2 weight percent maleic anhydride.

5. The thermoplastic polymer composition of claim 1 wherein the modified polyethylene comprises a low-density polyethylene.

6. The thermoplastic polymer composition of claim 1 wherein the modified polyethylene comprises a linear low-density polyethylene.

7. The thermoplastic polymer composition of claim 1 wherein the modified polyethylene comprises a high-density polyethylene.

8. The thermoplastic polymer composition of claim 1 wherein the modified polyethylene, polypropylene or a poly(ethylene-co-propylene) resin comprises a cyclodextrin bonded to an epoxy modified polyolefin.

9. The thermoplastic polymer composition of claim 1 wherein the substituent comprises azido, amino, acetylamino, alkylamino, hydroxyalkyl, heterocyclyl, alkylsulfonate, hydroxyalkylthio, or aminoalkylthio.

10. The thermoplastic composition of claim 1 wherein the modified resin comprises a packaging grade vinyl polymer.

11. The thermoplastic composition of claim 1 wherein the composition has a higher percent of crystallinity than the polyolefin without cyclodextrin.

12. The thermoplastic composition of claim 1 wherein the composition has a higher polarity and a lower equilibrium partition coefficient than the polyolefin without cyclodextrin.

13. The thermoplastic composition of claim 1 wherein the composition has selective barrier properties.

14. The thermoplastic composition of claim 1 further comprising a thermoplastic resin comprising a poly(ethylene-co-vinyl acetate), polyvinyl chloride, polyvinylidene chloride, butyl rubber, styrene-butadiene rubber, or acrylic rubber.

15. The thermoplastic composition of claim 1 further comprising a lubricant, an antistatic agent, a plasticizer, a heat stabilizer, an antioxidant, or a pigment.