CA2536268A1 - Ionomeric oxygen scavenger compositions - Google Patents
Ionomeric oxygen scavenger compositions Download PDFInfo
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- CA2536268A1 CA2536268A1 CA 2536268 CA2536268A CA2536268A1 CA 2536268 A1 CA2536268 A1 CA 2536268A1 CA 2536268 CA2536268 CA 2536268 CA 2536268 A CA2536268 A CA 2536268A CA 2536268 A1 CA2536268 A1 CA 2536268A1
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D81/00—Containers, packaging elements, or packages, for contents presenting particular transport or storage problems, or adapted to be used for non-packaging purposes after removal of contents
- B65D81/24—Adaptations for preventing deterioration or decay of contents; Applications to the container or packaging material of food preservatives, fungicides, pesticides or animal repellants
- B65D81/26—Adaptations for preventing deterioration or decay of contents; Applications to the container or packaging material of food preservatives, fungicides, pesticides or animal repellants with provision for draining away, or absorbing, or removing by ventilation, fluids, e.g. exuded by contents; Applications of corrosion inhibitors or desiccators
- B65D81/266—Adaptations for preventing deterioration or decay of contents; Applications to the container or packaging material of food preservatives, fungicides, pesticides or animal repellants with provision for draining away, or absorbing, or removing by ventilation, fluids, e.g. exuded by contents; Applications of corrosion inhibitors or desiccators for absorbing gases, e.g. oxygen absorbers or desiccants
- B65D81/268—Adaptations for preventing deterioration or decay of contents; Applications to the container or packaging material of food preservatives, fungicides, pesticides or animal repellants with provision for draining away, or absorbing, or removing by ventilation, fluids, e.g. exuded by contents; Applications of corrosion inhibitors or desiccators for absorbing gases, e.g. oxygen absorbers or desiccants the absorber being enclosed in a small pack, e.g. bag, included in the package
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6888—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/06—Polyethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/70—Other properties
- B32B2307/74—Oxygen absorber
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2439/00—Containers; Receptacles
- B32B2439/70—Food packaging
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31971—Of carbohydrate
- Y10T428/31993—Of paper
Abstract
A film, laminated product, and other packaging materials are disclosed, each including an oxygen scavenger composition including mer units derived from a substituted alicyclic compound having non-aromatic, ethylenic functionality, mer units including an ionomeric group, and mer units of a di- or polyfunctional hydrocarbon compound. Certain oxygen scavenger compositions have been found to act as an oxygen scavenger under both ambient and refrigeration conditions, to be compatible with conventional film forming packaging materials, to inhibit undesirable oligomer formation and oxidation by-product formation, and to be readily formable and processable using conventional film forming equipment.
Claims (22)
1. ~A film comprising at least one layer, the layer comprising an oxygen scavenger composition comprising a condensation,polymer and a transition metal salt, compound or complex, wherein said polymer comprises mer units derived from (A) ~at least one or a mixture of substituted alicyclic compounds having non-aromatic, ethylenic functionality according to the following representation:
wherein A, B, C1, C2, C3, C4 each independently represents hydrogen or a C q H2q+1 hydrocarbyl group with q being an integer in the range of from 0 to 20, provided that either A or B and at least one of C1, C2, C3, C4 are hydrogen atoms and each carbon atom of the alicyclic ring is fully substituted by groups selected from hydrogen, hydrocarbyl X or Y groups or mixtures thereof to fill its valence state;
X and Y each independently or together represents functional groups that is capable of being part of a heteroatom containing linkage forming a covalent bond linkage between the cycloalkenyl containing group and other monomeric groups forming the condensation polymer; and Z being selected from a -(C t H2t-2) hydrocarbyl group with t being an integer in the range from 1-4;
(B) ~at least one or a mixture of substituted non-aromatic or aromatic hydrocarbyl compounds having ionomeric functionality according to the~
following representation:
wherein R represents a non-aromatic or aromatic hydrocarbon group;
each F independently or two F groups together represent a functional group capable of being part of a heteroatam containing linkage between the hydrocarbon group R and other monomeric groups forming the condensation polymer;
E represents an anionic group selected from sulfonyl or carboxyl group;
M represents a cationic alkali metal ion or cationic alkaline earth metal ion; and "a" represents an integer having the value equal to the numerical value of the valence of M; and (C) ~at least one or a mixture of di- or polyfunctional hydrocarbon compounds according to the following representation:
G-R' (-G) x wherein R' represents a non-aromatic or aromatic hydrocarbon group; and each G independently represents a functional group capable of being part of a heteroatom containing linkage between the hydrocarbon group R' and the other monomeric groups forming the condensation polymer, and x is at least 1.
wherein A, B, C1, C2, C3, C4 each independently represents hydrogen or a C q H2q+1 hydrocarbyl group with q being an integer in the range of from 0 to 20, provided that either A or B and at least one of C1, C2, C3, C4 are hydrogen atoms and each carbon atom of the alicyclic ring is fully substituted by groups selected from hydrogen, hydrocarbyl X or Y groups or mixtures thereof to fill its valence state;
X and Y each independently or together represents functional groups that is capable of being part of a heteroatom containing linkage forming a covalent bond linkage between the cycloalkenyl containing group and other monomeric groups forming the condensation polymer; and Z being selected from a -(C t H2t-2) hydrocarbyl group with t being an integer in the range from 1-4;
(B) ~at least one or a mixture of substituted non-aromatic or aromatic hydrocarbyl compounds having ionomeric functionality according to the~
following representation:
wherein R represents a non-aromatic or aromatic hydrocarbon group;
each F independently or two F groups together represent a functional group capable of being part of a heteroatam containing linkage between the hydrocarbon group R and other monomeric groups forming the condensation polymer;
E represents an anionic group selected from sulfonyl or carboxyl group;
M represents a cationic alkali metal ion or cationic alkaline earth metal ion; and "a" represents an integer having the value equal to the numerical value of the valence of M; and (C) ~at least one or a mixture of di- or polyfunctional hydrocarbon compounds according to the following representation:
G-R' (-G) x wherein R' represents a non-aromatic or aromatic hydrocarbon group; and each G independently represents a functional group capable of being part of a heteroatom containing linkage between the hydrocarbon group R' and the other monomeric groups forming the condensation polymer, and x is at least 1.
2. ~The film of claim 1 wherein (A) comprises a monomer selected from 3-cycohexene-1,1- dimethanol, tetrahydrophthalic acid, dimethyl tetrahydrophthalate, tetrahydrophthalic anhydride, and mixtures thereof.
3. ~The film of claim 1 wherein (B) is selected from dimethyl-5-sulfoisophthalate, alkali metal salt or 5-sulfoisophthalic acid, alkali metal salt.
4. ~The film of claim 1 wherein (C) is selected from aliphatic or aromatic diacids, diols, diamines, diisocyanates or polyols selected from C2-C20 alkylene glycol or polyalkylene glycol.
5. ~The film of claim 1 wherein the functional groups of each of the monomers (A), (B) and (C) are selected from carboxylic acid, acid ester, acid anhydride, acid halide, isocyano, hydroxyl or amino groups; said groups are present in a molar ratio of carboxylic acid, acid ester, acid anhydride, acid halide and isocyano groups to hydroxyl and amino groups of from 0.9:1 to 1.1:1; and said mer units derived from (B) are present in from 0.25 to 20 molar percent of said codensation polymer.
6. ~A laminated product comprising a plurality of layers, including i) at least one layer, the layer comprising an oxygen scavenger composition comprising a condensation polymer and a transition metal salt, compound or complex, wherein said polymer comprises mer units derived from (A) at least one or a mixture of substituted alicyclic compounds having non-aromatic, ethylenic functionality according to the following representation:
wherein A, B, C1, C2, C3, C4 each independently represents hydrogen or a C q H2q+1 hydrocarbyl group with q being an integer in the range of from 0 to 20, provided that either A or B and at least one of C1, C2, C3, C4 are hydrogen atoms and each carbon atom of the alicyclic ring is fully substituted by groups selected from hydrogen, hydrocarbyl X or Y groups or mixtures thereof;
X and Y each independently or together represents functional groups that is capable of being part of a heteroatom containing linkage forming a covalent bond linkage between the cycloalkenyl containing group and other monomeric groups forming the condensation polymer; and Z being selected from a -(C t H2t-2) hydrocarbyl group with t being an integer in the range from 1-4;
(B) ~at least one or a mixture of substituted non-aromatic or aromatic hydrocarbyl compounds having ionomeric functionality according to the following representation:
wherein R represents a non-aromatic or aromatic hydrocarbon group;
each F independently or two F groups together represent a functional group capable of being part of a heteroatam containing linkage between the hydrocarbon group R and other monomeric groups forming the condensation polymer;
E represents an anionic group selected from sulfonyl or carboxyl group;
M represents a cationic alkali metal ion or cationic alkaline earth metal ion; and "a" represents an integer having the value equal to the numerical value of the valence of M; and (C) ~at least one or a mixture of di- or polyfunctional hydrocarbon compounds according to the following representation:
G-R'(-G) x wherein R' represents a non-aromatic or aromatic hydrocarbon group; and each G independently represents a functional group capable of being part of a heteroatom containing linkage between the hydrocarbon group R' and the other monomeric groups forming the condensation polymer, and x is at least 1; and ii) ~at least one layer comprising a material selected from the group consisting of a) ~a polymeric article, b) ~a paper article, and c) ~a metal article.
wherein A, B, C1, C2, C3, C4 each independently represents hydrogen or a C q H2q+1 hydrocarbyl group with q being an integer in the range of from 0 to 20, provided that either A or B and at least one of C1, C2, C3, C4 are hydrogen atoms and each carbon atom of the alicyclic ring is fully substituted by groups selected from hydrogen, hydrocarbyl X or Y groups or mixtures thereof;
X and Y each independently or together represents functional groups that is capable of being part of a heteroatom containing linkage forming a covalent bond linkage between the cycloalkenyl containing group and other monomeric groups forming the condensation polymer; and Z being selected from a -(C t H2t-2) hydrocarbyl group with t being an integer in the range from 1-4;
(B) ~at least one or a mixture of substituted non-aromatic or aromatic hydrocarbyl compounds having ionomeric functionality according to the following representation:
wherein R represents a non-aromatic or aromatic hydrocarbon group;
each F independently or two F groups together represent a functional group capable of being part of a heteroatam containing linkage between the hydrocarbon group R and other monomeric groups forming the condensation polymer;
E represents an anionic group selected from sulfonyl or carboxyl group;
M represents a cationic alkali metal ion or cationic alkaline earth metal ion; and "a" represents an integer having the value equal to the numerical value of the valence of M; and (C) ~at least one or a mixture of di- or polyfunctional hydrocarbon compounds according to the following representation:
G-R'(-G) x wherein R' represents a non-aromatic or aromatic hydrocarbon group; and each G independently represents a functional group capable of being part of a heteroatom containing linkage between the hydrocarbon group R' and the other monomeric groups forming the condensation polymer, and x is at least 1; and ii) ~at least one layer comprising a material selected from the group consisting of a) ~a polymeric article, b) ~a paper article, and c) ~a metal article.
7. ~The laminated product of claim 6 wherein (A) comprises a monomer selected from 3-cycohexene-1,1- dimethanol, tetrahydrophthalic acid, dimethyl tetrahydrophthalate, tetrahydrophthalic anhydride, and mixtures thereof.
8. The laminated product of claim 6wherein (B) is selected from dimethyl-5-sulfoisophthalate, alkali metal salt or 5-sulfoisophthalic acid, alkali metal salt.
9. The laminated product of claim 6 wherein (C) is selected from aliphatic or aromatic diacids, diols, diamines, diisocyanates or polyols selected from C2-C20 alkylene glycol or polyalkylene glycol.
10. The laminated product of claim 6 wherein the functional groups of each of the monomers (A), (B) and (C) are selected from carboxylic acid, acid ester, acid anhydride, acid halide, isocyano, hydroxyl or amino groups;
said groups are present in a molar ratio of carboxylic acid, acid ester, acid anhydride, acid halide and isocyano groups to hydroxyl and amino groups of from 0.9:1 to 1.1:1; and said mer units derived from (B) are present in from 0.25 to 20 molar percent of said codensation polymer.
said groups are present in a molar ratio of carboxylic acid, acid ester, acid anhydride, acid halide and isocyano groups to hydroxyl and amino groups of from 0.9:1 to 1.1:1; and said mer units derived from (B) are present in from 0.25 to 20 molar percent of said codensation polymer.
11. An oxygen scavenger composition comprising a condensation polymer and a transition metal salt, compound or complex, wherein said polymer comprises mer units derived from (A) at least one or a mixture of substituted alicyclic compounds having non-aromatic, ethylenic functionality according to the following representation:
wherein A, B, C1, C2, C3, C4 each independently represents hydrogen or a C q H2a+1 hydrocarbyl group with q being an integer in the range of from 0 to 20, provided that either A or B and at least one of C1, C2, C3, C4 are hydrogen atoms and each carbon atom of the alicyclic ring is fully substituted by groups selected from hydrogen, hydrocarbyl X or Y groups or mixtures thereof;
X and Y each independently or together represents functional groups that is capable of being part of a heteroatom containing linkage forming a covalent bond linkage between the cycloalkenyl containing group and other monomeric groups forming the condensation polymer; and Z being selected from a -(C t H2t-2) hydrocarbyl group with t being an integer in the range from 1-4;
(B) at least one or a mixture of substituted non-aromatic or aromatic hydrocarbyl compounds having ionomeric functionality according to the following representation:
wherein R represents a non-aromatic or aromatic hydrocarbon group;
each F independently or two F groups together represent a functional group capable of being part of a heteroatam containing linkage between the hydrocarbon group R and other monomeric groups forming the condensation polymer;
E represents an anionic group selected from sulfonyl or carboxyl group;
M represents a cationic alkali metal ion or cationic alkaline earth metal ion; and "a" represents an integer having the value equal to the numerical value of the valence of M; and (C) at least one or a mixture of di- or polyfunctional hydrocarbon compounds according to the following representation:
G-R' (-G)x wherein R' represents a non-aromatic or aromatic hydrocarbon group; and each G independently represents a functional group capable of being part of a heteroatom containing linkage between the hydrocarbon group R' and the other monomeric groups forming the condensation polymer, and x is at least 1.
wherein A, B, C1, C2, C3, C4 each independently represents hydrogen or a C q H2a+1 hydrocarbyl group with q being an integer in the range of from 0 to 20, provided that either A or B and at least one of C1, C2, C3, C4 are hydrogen atoms and each carbon atom of the alicyclic ring is fully substituted by groups selected from hydrogen, hydrocarbyl X or Y groups or mixtures thereof;
X and Y each independently or together represents functional groups that is capable of being part of a heteroatom containing linkage forming a covalent bond linkage between the cycloalkenyl containing group and other monomeric groups forming the condensation polymer; and Z being selected from a -(C t H2t-2) hydrocarbyl group with t being an integer in the range from 1-4;
(B) at least one or a mixture of substituted non-aromatic or aromatic hydrocarbyl compounds having ionomeric functionality according to the following representation:
wherein R represents a non-aromatic or aromatic hydrocarbon group;
each F independently or two F groups together represent a functional group capable of being part of a heteroatam containing linkage between the hydrocarbon group R and other monomeric groups forming the condensation polymer;
E represents an anionic group selected from sulfonyl or carboxyl group;
M represents a cationic alkali metal ion or cationic alkaline earth metal ion; and "a" represents an integer having the value equal to the numerical value of the valence of M; and (C) at least one or a mixture of di- or polyfunctional hydrocarbon compounds according to the following representation:
G-R' (-G)x wherein R' represents a non-aromatic or aromatic hydrocarbon group; and each G independently represents a functional group capable of being part of a heteroatom containing linkage between the hydrocarbon group R' and the other monomeric groups forming the condensation polymer, and x is at least 1.
12. The composition of claim 11 wherein said condensation polymer comprises from 40 to 60 molar percent (A), from 0.25 to 20 molar percent (B), and from 40 to 60 molar percent (C).
13. The composition of claim 11 wherein functional groups X, Y, F, and G are each independently selected from the group consisting of -(CH2)n-OH, -(CH2)n-NH2, -(CH2)n-N=C=O and -(CH2)n-C=O)-D with n being an integer in the range from 0 to 20 and D being selected from a halide atom or an OR group wherein R is an -H or C1-C12 alkyl group, or X and Y together, two F groups together or two G groups together represent -((CH2)n-C=O)x-D with n being an integer in the range from 0 to 20, D is oxygen atom and x is 2.
14. The composition of claim 11 wherein (A), (B) and (C) have functional groups such that the molar ratio of hydroxyl and amino functional groups to carboxylic acid, carboxylic acid ester, carboxylic acid halide and isocyano functional groups is from 0.9:1 to 1.1:1.
15. The composition of claim 11 wherein (A) comprises alicyclic units selected from substituted cyclohexene; and Z being -(C t H2t-2) with t being 1.
16. The composition of claim 11 wherein (A) comprises a monomer selected from 3-cycohexene-1,1-dimethanol, tetrahydrophthalic acid, dimethyl tetrahydrophthalate, tetrahydrophthalic anhydride, and mixtures thereof.
17. The composition of claim 11 wherein (B) is selected from dimethyl-5-sulfoisophthalate, alkali metal salt or 5-sulfoisophthalic acid, alkali metal salt.
18. The composition of claim 11wherein (C) is selected from aliphatic or aromatic diacids, diols, diamines, diisocyanates or polyols selected from C2-C20 alkylene glycol or polyalkylene glycol.
19. The composition of claim 11 wherein (C) is selected from C2-C20 alkylene glycol, C4-C8 alkylene glycol, poly(C2-C4 alkylene) glycol, and 3-cyclohexene-1,1-dimethanol.
20.. The composition of claim 11 wherein the transition metal salt is selected from the group consisting of cobalt neodecanoate, cobalt 2-ethylhexanoate, cobalt oleate, cobalt acetylacetonate, and cobalt 2-ethylbutyrate.
21. The composition of claim 11 wherein the composition comprises an effective amount of a photoinitiator.
22. The composition of claim 11 wherein the composition comprises a diluent polymer selected from the group consisting of polyester, polyamides, polycarbonates, polyurethanes and polyethers, ethylene polymers or copolymers, acrylate polymers, ethylene-vinyl alcohol copolymer, polypropylene and polypropylene copolymers, styrene polymers and styrene copolymers, vinyl chloride polymer and vinyl chloride copolymers, polyvinylidene polymers and copolymers and mixtures thereof.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/649,739 | 2003-08-28 | ||
| US10/649,739 US6872451B2 (en) | 2003-08-28 | 2003-08-28 | Ionomeric oxygen scavenger compositions |
| PCT/US2004/025595 WO2005023674A2 (en) | 2003-08-28 | 2004-08-26 | Ionomeric oxygen scavenger compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2536268A1 true CA2536268A1 (en) | 2005-03-17 |
| CA2536268C CA2536268C (en) | 2011-08-16 |
Family
ID=34217001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2536268 Expired - Fee Related CA2536268C (en) | 2003-08-28 | 2004-08-26 | Ionomeric oxygen scavenger compositions |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6872451B2 (en) |
| EP (1) | EP1664152B1 (en) |
| AT (1) | ATE527299T1 (en) |
| AU (1) | AU2004270650B2 (en) |
| CA (1) | CA2536268C (en) |
| NZ (1) | NZ545399A (en) |
| WO (1) | WO2005023674A2 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8465818B2 (en) * | 2005-10-07 | 2013-06-18 | M & G Usa Corporation | Polyamides and polyesters blended with a lithium salt interfacial tension reducing agent |
| EP2021395A1 (en) * | 2006-06-01 | 2009-02-11 | E.I. Du Pont De Nemours And Company | Conductive polymer compositions |
| US20080161465A1 (en) * | 2006-12-28 | 2008-07-03 | Jason Christopher Jenkins | Oxygen-scavenging polyester compositions useful for packaging |
| US7521523B2 (en) * | 2006-12-28 | 2009-04-21 | Eastman Chemical Company | Oxygen-scavenging polyester compositions useful in packaging |
| US20080161529A1 (en) * | 2006-12-28 | 2008-07-03 | Jason Christopher Jenkins | Oxygen-scavenging polyesters useful for packaging |
| ATE466816T1 (en) * | 2007-02-20 | 2010-05-15 | Koninkl Philips Electronics Nv | BEVERAGE DISPENSING DEVICE WITH PUMPING LOW OXYGEN AIR INTO A BARREL |
| US8815360B2 (en) * | 2007-08-28 | 2014-08-26 | Cryovac, Inc. | Multilayer film having passive and active oxygen barrier layers |
| US9452592B2 (en) * | 2007-08-28 | 2016-09-27 | Cryovac, Inc. | Multilayer film having an active oxygen barrier layer with radiation enhanced active barrier properties |
| US8262952B2 (en) * | 2007-10-31 | 2012-09-11 | Bausch & Lomb Incorporated | Molds for production of ophthalmic devices |
| DE102014108530A1 (en) * | 2014-06-17 | 2015-12-17 | B. Braun Avitum Ag | Method for sterilizing a hollow fiber filter module, hollow fiber filter module with closure and oxygen absorbing closure |
| JP5862988B2 (en) * | 2014-10-22 | 2016-02-16 | 住友ベークライト株式会社 | Laminated film and package |
| CN110183780A (en) * | 2019-06-14 | 2019-08-30 | 国家能源投资集团有限责任公司 | Polypropylene wiredrawing material, its PP Pipe Compound and BOPP film product |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE1900181A1 (en) | 1968-02-05 | 1969-10-02 | Akademie Der Wissenschaften Be | Producing polyesters from dicarb acid anhydrides and |
| US4702966A (en) | 1981-01-23 | 1987-10-27 | American Can Company | Oxygen scavenger |
| US4536409A (en) | 1981-01-23 | 1985-08-20 | American Can Company | Oxygen scavenger |
| DE301719T1 (en) | 1987-07-27 | 1990-12-20 | Mb Group Plc, Reading, Berkshire, Gb | PACKAGING AGENTS. |
| US5281360A (en) | 1990-01-31 | 1994-01-25 | American National Can Company | Barrier composition and articles made therefrom |
| FR2673946B1 (en) | 1991-03-15 | 1993-05-28 | Atochem | POLYETHER BLOCK AMIDES, THEIR SYNTHESIS PROCESS. |
| CA2062083C (en) * | 1991-04-02 | 2002-03-26 | Drew Ve Speer | Compositions, articles and methods for scavenging oxygen |
| ZA921914B (en) | 1991-04-02 | 1993-09-16 | Grace W R & Co | Compositions, articles and methods for scavenging oxygen |
| US5211875A (en) | 1991-06-27 | 1993-05-18 | W. R. Grace & Co.-Conn. | Methods and compositions for oxygen scavenging |
| US5399289A (en) | 1992-10-01 | 1995-03-21 | W. R. Grace & Co.-Conn. | Compositions, articles and methods for scavenging oxygen which have improved physical properties |
| US5604043A (en) | 1993-09-20 | 1997-02-18 | W.R. Grace & Co.-Conn. | Heat shrinkable films containing single site catalyzed copolymers having long chain branching |
| US5736616A (en) | 1993-07-13 | 1998-04-07 | Chevron Chemical Company | Compositions having ethylenic backbone and benzylic allylic or ether-containing side-chains oxygen scavenging compositions containing same and process for making these compositions by esterification or transesterification of a polymer melt |
| WO1996040799A1 (en) | 1995-06-07 | 1996-12-19 | Chevron Chemical Company | Compositions having ethylenic backbone and benzylic, allylic, or ether-containing side-chains, oxygen scavenging compositions containing same, and process for making these compositions by esterification or transesterification of a polymer melt |
| US6083585A (en) * | 1996-09-23 | 2000-07-04 | Bp Amoco Corporation | Oxygen scavenging condensation copolymers for bottles and packaging articles |
| DK0932561T3 (en) | 1996-09-23 | 2000-08-28 | Bp Amoco Corp | Plastic bottle without oxygen penetration for beer and other uses |
| CA2325404C (en) | 1998-03-25 | 2007-07-10 | Chevron Phillips Chemical Company Lp | Oxygen scavengers with reduced oxidation products for use in plastic films and beverage and food containers |
| US6254803B1 (en) | 1998-03-25 | 2001-07-03 | Cryovac, Inc. | Oxygen scavengers with reduced oxidation products for use in plastic films |
| JP2001031759A (en) * | 1999-07-23 | 2001-02-06 | Showa Denko Kk | Polycondensation-based oxygen capturing polymer having unsaturated bond in barching chain |
| US6527976B1 (en) * | 2000-11-27 | 2003-03-04 | Chenron Phillips Chemical Company Lp | Epoxy-, melamine- and isocyanate cured oxygen scavenging compositions and methods of preparing the same |
| US20020142168A1 (en) * | 2000-12-22 | 2002-10-03 | Speer Drew V. | Process for pasteurizing an oxygen sensitive product and triggering an oxygen scavenger, and the resulting package |
| US6544611B2 (en) | 2001-08-01 | 2003-04-08 | Arteva North America S.A.R.L. | Oxygen scavenging PET based polymer |
-
2003
- 2003-08-28 US US10/649,739 patent/US6872451B2/en not_active Expired - Fee Related
-
2004
- 2004-08-26 CA CA 2536268 patent/CA2536268C/en not_active Expired - Fee Related
- 2004-08-26 AU AU2004270650A patent/AU2004270650B2/en not_active Ceased
- 2004-08-26 NZ NZ545399A patent/NZ545399A/en not_active IP Right Cessation
- 2004-08-26 EP EP20040780433 patent/EP1664152B1/en not_active Not-in-force
- 2004-08-26 WO PCT/US2004/025595 patent/WO2005023674A2/en active Application Filing
- 2004-08-26 AT AT04780433T patent/ATE527299T1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE527299T1 (en) | 2011-10-15 |
| NZ545399A (en) | 2009-12-24 |
| AU2004270650A1 (en) | 2005-03-17 |
| AU2004270650B2 (en) | 2010-06-10 |
| WO2005023674A3 (en) | 2005-05-26 |
| EP1664152A2 (en) | 2006-06-07 |
| US20050048286A1 (en) | 2005-03-03 |
| WO2005023674A2 (en) | 2005-03-17 |
| US6872451B2 (en) | 2005-03-29 |
| EP1664152B1 (en) | 2011-10-05 |
| CA2536268C (en) | 2011-08-16 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20220301 |
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| MKLA | Lapsed |
Effective date: 20200831 |