# US 8,148,466 B2 · Amphoteric grafted barrier materials > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,148,466 B2 - Document ID: US8148466B2 - Status: Granted - Kind: B2 - Application number: 11/136,084 - Filed: 2005-05-23 - Published: 2005-11-24 - Granted: 2012-04-03 - Earliest claimed: 2004-05-24 - Assignees: Cellresin Technologies, LLC - Inventors: Willard E. Wood; Neil J. Beaverson - Web page: https://patentgrep.com/patent/US8148466B2 ## CPC - C08F 255/00: Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 - C08F 255/02: on to polymers of olefins having two or three carbon atoms - C08F 291/00: Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00 - C08L 51/06: grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract Thermoplastic polymer compositions, films, containers, laminates and fibers can comprise a modified polymer. The said modified polymer having a moiety comprising a half-ester reaction product of cyclodextrin and metal and/or organic group covalently bonded to some portion of the half-acid moieties. The cyclodextrin compound, grafted to the polymer structure, can scavenge impurities, permeants, or other undesirable volatile contaminants. The cooperation between the modified polymer's carboxylic acidic groups, basic groups and grafted cyclodextrin can provide active barrier properties to a film, web, fiber or other polymer structure. A permeant or a contaminant can be complexed or trapped within the polymer and held within the film, web or fiber preventing the permeant from passing into the interior of a container, or the contaminant can be scavenged from the enclosed headspace or surrounding environment. ## Claims ### Claim 1 A thermoplastic polymer composition, the composition capable of formation into thermoplastic fiber, film, fabric or web, consisting essentially of: (a) a blend of a polyolefin resin and an anhydride-modified polyolefin resin, (b) a stoichiometric reaction product of a cyclodextrin and the anhydride-modified polyolefin resin, and (c) an alkaline earth metal on the anhydride-modified polyolefin resin; wherein the polymer composition has a tri-functional trapping mechanism, the trapping mechanism consisting of carboxylic acid groups corresponding to the anhydride, the anhydride half-ester product of cyclodextrin, and a metal or organic group bonded to some portion of the anhydride half-acid groups; wherein the cyclodextrin is substantially free of an inclusion complex including residual polymer contaminant. ### Claim 2 (depends on 1) The thermoplastic polymer composition of claim 1, wherein the modified polyolefin resin comprises a polymethylene backbone comprising randomly substituted covalently bonded maleic groups comprising a cyclodextrin compound. ### Claim 3 (depends on 1) The thermoplastic polymer composition of claim 1 wherein the modified polyolefin resin comprises polyethylene or copolymers of polyethylene. ### Claim 4 (depends on 1) The thermoplastic polymer composition of claim 1 wherein the modified polyolefin resin comprises polypropylene or copolymers of polypropylene. ### Claim 5 (depends on 1) The thermoplastic polymer composition of claim 1 wherein the anhydride group is derived from maleic anhydride, citraconic anhydride, itaconic anhydride or their corresponding acids including fumaric acid. ### Claim 6 (depends on 1) The thermoplastic polymer composition of claim 1, wherein the modified polyolefin resin comprises an alpha, beta or gamma cyclodextrin or mixture thereof bonded to a backbone carbon of the polymer through a maleic moiety or to a carbon in a pendent group through a maleic moiety. ### Claim 7 (depends on 6) The thermoplastic polymer composition of claim 6 wherein the modified polyolefin resin comprises polyethylene or copolymers of polyethylene. ### Claim 8 (depends on 6) The thermoplastic polymer composition of claim 6 wherein the modified polyolefin resin comprises polypropylene or copolymers of polypropylene. ### Claim 9 (depends on 1) A thermoplastic polymer composition of claim 1, wherein the modified polyolefin resin comprises a cyclodextrin derivative having at least one substituent group on the cyclodextrin ring. ### Claim 10 (depends on 9) The thermoplastic polymer composition of claim 9 wherein the modified polyolefin resin comprises polyethylene or copolymers of polyethylene. ### Claim 11 (depends on 9) The thermoplastic polymer composition of claim 9 wherein the modified polyolefin resin comprises polypropylene or copolymers of polypropylene. ### Claim 12 A thermoplastic film consisting essentially of: (a) a blend of a polyolefin resin and an anhydride-modified polyolefin resin, (b) a stoichiometric reaction product of a anhydride-modified polyolefin resin, and (c) an alkaline earth metal on the anhydride-modified polyolefin resin to scavenge acidic molecules; wherein the polymer composition has a tri-functional trapping mechanism, the trapping mechanism consisting of carboxylic acid groups corresponding to the anhydride, the anhydride half-ester product of cyclodextrin, and a metal or organic group bonded to some portion of the anhydride half-acid groups; wherein the cyclodextrin is substantially free of an inclusion complex including residual polymer contaminant and can retain the ability to trap or complex diffusing permeant in the central pore of the cyclodextrin. ### Claim 13 (depends on 12) The film of claim 12, wherein the modified polyolefin resin comprises a polymethylene backbone comprising randomly substituted covalently bonded groups maleic anhydride comprising a cyclodextrin compound. ### Claim 14 (depends on 12) The film of claim 12 wherein the modified polyolefin resin comprises polyethylene or copolymers of polyethylene. ### Claim 15 (depends on 12) The film of claim 12 wherein the modified polyolefin resin comprises polypropylene or copolymers of polypropylene. ### Claim 16 (depends on 12) The film of claim 12 wherein the anhydride group is derived from maleic acid, citraconic acid, itaconic acid or fumaric acid. ### Claim 17 (depends on 12) The film of claim 12, wherein the modified polyolefin resin comprises an alpha, beta or gamma cyclodextrin or mixtures thereof bonded to a backbone carbon of the polymer through a maleic moiety or to a carbon in a pendent group through a maleic moiety. ### Claim 18 (depends on 12) A film of claim 12, wherein the modified polyolefin resin comprises a cyclodextrin derivative having at least one substituent group on the cyclodextrin ring. ### Claim 19 (depends on 18) The film of claim 18 wherein the modified polyolefin resin comprises polyethylene. ### Claim 20 (depends on 18) The film of claim 18 wherein the modified polyolefin resin comprises polypropylene. ### Claim 21 A thermoplastic fiber consisting essentially of: (a) a blend of a polyolefin resin and an anhydride-modified polyolefin resin, (b) a stoichiometric reaction product of a cyclodextrin and the anhydride-modified polyolefin resin, and (c) an alkaline earth metal on the anhydride-modified polyolefin resin to scavenge acidic molecules; wherein the polymer composition has a tri-functional trapping mechanism, the trapping mechanism consisting of carboxylic acid groups corresponding to the anhydride, the anhydride half-ester product of cyclodextrin, and a metal or organic group bonded to some portion of the anhydride half-acid groups; wherein the cyclodextrin is substantially free of an inclusion complex including residual polymer contaminant. ### Claim 22 (depends on 21) The fiber of claim 21, wherein the modified polyolefin resin comprises a polymethylene backbone comprising substituted covalently bonded groups comprising a cyclodextrin compound. ### Claim 23 (depends on 21) The fiber of claim 21 wherein the modified polyolefin resin comprises polyethylene. ### Claim 24 (depends on 21) The fiber of claim 21 wherein the modified polyolefin resin comprises polypropylene. ### Claim 25 (depends on 21) The fiber of claim 21 wherein the anhydride group is derived from maleic acid or fumaric acid. ### Claim 26 (depends on 21) The fiber of claim 21, wherein the modified polyolefin resin comprises an alpha, beta or gamma cyclodextrin or mixtures thereof bonded to a backbone carbon of the polymer through a maleic moiety or to a carbon in a pendent group through a maleic moiety. ### Claim 27 (depends on 26) The fiber of claim 26 wherein the modified polyolefin resin comprises polyethylene. ### Claim 28 (depends on 27) The fiber of claim 27 wherein the modified polyolefin resin comprises polypropylene. ### Claim 29 (depends on 1) A multi-layered fabric comprising fibers comprising the polymer of claim 1. ### Claim 30 (depends on 1) A nonwoven fabric comprising fibers comprising the polymer of claim 1. ### Claim 31 (depends on 1) The polymer composition of claim 1 wherein some portion of the carboxylic acid groups corresponding to the anhydride are neutralized with a metal cation. ### Claim 32 (depends on 12) The polymer composition of claim 12 wherein some portion of the carboxylic acid groups corresponding to the anhydride are neutralized with a metal cation. ### Claim 33 (depends on 21) The polymer composition of claim 21 wherein some portion of the carboxylic acid groups corresponding to the anhydride are neutralized with a metal cation.