US 7,754,798 B2Granted

Oxygen scavenger block copolymers and compositions

AssigneeCryovac, Inc.

InventorsCynthia L. Ebner, Arthur L. Berrier

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Abstract

An oxygen scavenger composition includes a block co-polymer having at least one block including a polyester condensation polymer segment having cycloalkenyl group(s) or functionality directly or indirectly bonded to the polymer chain of said block, and having at least one second block including a polymer segment of a thermoplastic, film forming material. The block copolymer has been found to act as an oxygen scavenger agent under both ambient and refrigerated conditions, to be compatible with conventional film forming packaging materials, and to provide compositions exhibiting low tack which can be readily formed and processed using conventional film forming equipment. A packaging material, such as a film or laminated product suitable for packaging applications, can include the oxygen scavenger composition.

Claims28

Dependent claims

A film comprising at least one layer, the layer comprising an oxygen scavenger composition consisting essentially of a transition metal salt, compound or complex and a block copolymer, wherein said block copolymer comprises:

(A) at least one first prepolymer (PA) block segment composed of 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 CqH2q+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 groups, Y groups and mixtures thereof;
X and Y each independently or together represents functional groups capable of being part of a heteroatom containing linkage forming a covalent bond linkage between the cycloalkenyl containing group and other mer groups forming the first polymer block segment;
and
Z being selected from a —(CtH2t)— hydrocarbylene group with t being an integer in the range from 1-4;
and
(b) 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 mer groups forming the first prepolymer block segment;
and
x is at least 1:
and
(B) at least one second prepolymer (PB) block segment derived from a monofunctional or polyfunctional polymers represented by the formula
P-(J)p
wherein
P represents a polymer capable of forming a film and being thermoplastic at temperatures higher than room temperature;
and
J represents functional group capable of being part of a heteroatom containing linkage forming a covalent bond linkage between the first prepolymer (PA) and the second prepolymer (PB) and p is 1 or 2;
wherein at least one functional group of prepolymer (PA) is capable of forming heteroatom containing linkage with functional group J of prepolymer (PB), polymer block segment (PA) is present in from 20 to 80 weight percent and polymer block segment (PB) is present in from 80 to 20 weight percent of said block copolymer and said prepolymer (PA) has a Tg of lower than about minus 20° C. and said prepolymer (PB) has a Tm of higher than +30° C.

21 more elements

A laminated product comprising a plurality of layers, including

i) at least one layer, the layer comprising an oxygen scavenger composition consisting essentially of a transition metal salt, compound or complex and a block copolymer, wherein said block copolymer comprises:
(A) at least one first prepolymer (PA) block segment composed of 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 CqH2q+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 groups, Y groups and mixtures thereof;
X and Y each independently or together represents functional groups capable of being part of a heteroatom containing linkage forming a covalent bond linkage between the cycloalkenyl containing group and other mer groups forming the first polymer block segment;
and
Z being selected from a —(CtH2t)— hydrocarbylene group with t being an integer in the range from 1-4;
and
(b) 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 mer groups forming the first prepolymer block segment;
and x is at least 1:
and
(B) at least one second prepolymer (PB) block segment derived from a monofunctional or polyfunctional polymers represented by the formula
P-(J)p
wherein
P represents a polymer capable of forming a film and being thermoplastic at temperatures higher than room temperature;
and
J represents functional group capable of being part of a heteroatom containing linkage forming a covalent bond linkage between the first prepolymer (PA) and the second prepolymer (PB) and p is 1 or 2;
wherein at least one functional group of prepolymer (PA) is capable of forming heteroatom containing linkage with functional group J of prepolymer (PB), polymer block segment (PA) is present in from 20 to 80 weight percent and polymer block segment (PB) is present in from 80 to 20 weight percent of said block copolymer and said prepolymer (PA) has a Tg of lower than about minus 20° C. and said prepolymer (PB) has a Tm of higher than +30° C.;
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.

26 more elements

An oxygen scavenger composition consisting essentially of a transition metal salt, compound or complex and a block copolymer, wherein said block copolymer comprises:

(A) at least one first prepolymer (PA) block segment composed of 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 CqH2q+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 groups, Y groups and mixtures thereof;
X and Y each independently or together represents functional groups capable of being part of a heteroatom containing linkage forming a covalent bond linkage between the cycloalkenyl containing group and other mer groups forming the first polymer block segment;
and
Z being selected from a —(CtH2t)— hydrocarbylene group with t being an integer in the range from 1-4;
and
(b) 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 mer groups forming the first prepolymer block segment;
and x is at least 1:
and
(B) at least one second prepolymer (PB) block segment derived from a monofunctional or polyfunctional polymers represented by the formula
P-(J)p
wherein
P represents a polymer capable of forming a film and being thermoplastic at temperatures higher than room temperature;
and
J represents functional group capable of being part of a heteroatom containing linkage forming a covalent bond linkage between the first prepolymer (PA) and the second prepolymer)(PB) and p is 1or 2;
wherein at least one functional group of prepolymer (PA) is capable of forming heteroatom containing linkage with functional group J of prepolymer (PB), polymer block segment (PA) is present in from 20 to 80 weight percent and polymer block segment (PB) is present in from 80 to 20 weight percent of said block copolymer percent of said block copolymer and said prepolymer (PA) has a Tg of lower than about minus 20° C. and said prepolymer (PB) has a Tm of higher than +30° C.

20 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/649,747Filed 28 Aug 2003
Published: US 2005/0048287 A13 Mar 2005
Granted: 13 Jul 2010
Term ends: Not estimatedThe source records don’t support an estimate.

Classification15 codes

B32B 27/18
Layered products comprising a layer of synthetic resin: characterised by the use of special additives
B01J 20/26
Comprising organic material: synthetic macromolecular compounds
B01J 20/262
Synthetic macromolecular compounds: obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by…
B01J 20/264
Synthetic macromolecular compounds: derived from different types of monomers, e.g. linear or branched copolymers, block copolymers, graft copolymers