# US 10,479,890 B2 · Oxygen scavenging polyester compositions for containers

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- Number: US 10,479,890 B2
- Document ID: US10479890B2
- Status: Granted
- Kind: B2
- Application number: 15/735,631
- Filed: 2016-06-10
- Published: 2018-10-25
- Granted: 2019-11-19
- Earliest claimed: 2015-06-12
- Assignees: APG Polytech, LLC
- Applicants: M&G USA Corporation
- Inventors: Gianluca Ferrari; D. Jeffrey Black
- Web page: https://patentgrep.com/patent/US10479890B2

## CPC

- C08L 91/00: Compositions of oils, fats or waxes; Compositions of derivatives thereof
- B29C 49/0005: {characterised by the material}
- C08K 3/22: of metals
- C08K 5/098: Metal salts of carboxylic acids
- C08K 5/103: with polyalcohols
- C08K 5/20: Carboxylic acid amides
- C08K 5/3445: Five-membered rings
- C08K 11/00: Use of ingredients of unknown constitution, e.g. undefined reaction products
- C08L 67/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence)
- C08L 67/03: the dicarboxylic acids and dihydroxy compounds having the carboxyl- and the hydroxy groups directly linked to aromatic rings
- C08L 77/06: Polyamides derived from polyamines and polycarboxylic acids (C08L77/10 takes precedence)
- B29C 49/06: Injection blow-moulding
- B29C 2949/0715: the preform having one end closed
- B29K 2067/003: {PET, i.e. poylethylene terephthalate}
- B29K 2105/0014: {Catalysts}
- B29K 2995/0053: bi-axially
- B29L 2031/7158: {Bottles}
- C08K 2003/2241: {Titanium dioxide}
- C08K 2201/012: Additives improving oxygen scavenging properties
- C08L 2201/08: Stabilised against heat, light or radiation or oxydation
- C08L 2203/10: used for bottles
- C08L 2203/16: used for films
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29L: INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES

## Abstract

Disclosed herein is an oxygen scavenging composition for containers. The oxygen scavenging composition for containers may comprise at least one polyester component, a transition metal catalyst, an oxygen scavenger, and a vegetable oil. The vegetable oil preferably comprises at least one molecule having a double allylic structure. The polyester component preferably comprises at least one acid unit and at least one diol unit. The concentration of double allylic structures of the vegetable oil in the composition may be greater than 5.0 meq/kg of all of the polyester components. The oxygen scavenger is preferably present in the composition at a level less than 1.0% by weight of the total composition. The vegetable oil is preferably present in the composition at a level greater than 0.3% by weight relative to the total weight of the polyester components, the transition metal catalyst and the vegetable oil.

## Claims

### Claim 1

An oxygen scavenging composition for containers comprising:
at least one polyester component,
a transition metal catalyst,
an oxygen scavenger, and
a vegetable oil comprising at least one molecule having a double allylic structure,
wherein the at least one polyester component comprises at least one acid unit and at least one diol unit, the concentration of the double allylic structures of the vegetable oil in the composition is greater than 5.0 meq/kg of all of the polyester components, the oxygen scavenger is present in the composition in a traditionally inert amount, and the vegetable oil is present in the composition at a level greater than 0.3% by weight relative to the total weight of the polyester components, the transition metal catalyst and the vegetable oil.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the at least one polyester component is a copolyester containing a metal sulfonate salt group.

### Claim 3 (depends on 2)

The composition of claim 2, wherein the metal sulfonate salt group is a metal sulfoisophthalate derived from a metal salt of 5-sulfoisophthalic acid, its dimethyl ester or its glycol ester.

### Claim 4 (depends on 3)

The composition of claim 3, wherein the metal salt of 5-sulfoisophthalic acid, its dimethyl ester or its glycol ester comprises a metal ion selected from the group consisting of Na+, Li+, K+, Zn2+, Mn2+, Co2+ and Ca2+.

### Claim 5 (depends on 2)

The composition of claim 2, wherein the metal sulfonate salt group is in a range selected from the group consisting of 0.01 to 10.0 mole percent, 0.01 to 2.0 mole percent, 0.05 to 1.1 mole percent, 0.10 to 0.74 mole percent and 0.10 to 0.6 mole percent based upon the total moles of acid units in all of the polyester components.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the transition metal catalyst is a compound containing at least one cobalt atom in a positive oxidation state.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the transition metal catalyst is a salt containing at least one cobalt atom in a positive oxidation state.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the transition metal catalyst is added to the composition at a level in a range selected from the group of between 10 and 600 ppm, between 20 and 400 ppm and between 40 and 200 ppm of metal relative to the total amount of the polyester components and vegetable oil present in the composition.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the vegetable oil is selected from the group consisting of flax seed oil, linseed oil, evening primrose oil, borage oil, sunflower oil, soybean oil, grapeseed oil, corn oil, cotton seed oil, rice bran oil, canola oil and peanut oil.

### Claim 10 (depends on 1)

The composition of claim 1, wherein the oxygen scavenger is a polyamide.

### Claim 11 (depends on 10)

The composition of claim 10, wherein the oxygen scavenger is present in the composition at a level in a range selected from the group consisting of between 0.1 and 0.9% by weight of the total composition, between 0.1 and 0.8% by weight of the total composition, between 0.1 and 0.7% by weight of the total composition and between 0.1 and 0.6% by weight of the total composition.

### Claim 12 (depends on 1)

The composition of claim 1, wherein the oxygen scavenger is poly-metaxylylene adipamide.

### Claim 13 (depends on 1)

The composition of claim 1, wherein the oxygen scavenger is selected from the group consisting of m-xylylenediamine-bis(phthalamide), N,N-bis(phenylmethyl)hexanediamide, N-allylic amide compounds, oligomer or polymers, N-benzylic amide compounds, oligomers or polymers and combinations thereof.

### Claim 14 (depends on 13)

The composition of claim 13, wherein the oxygen scavenger is present in the composition at a level in a range selected from the group consisting of between 0.1 and 5.0% by weight of the total composition, between 0.1 and 2.0% by weight of the total composition, between 0.1 and 1.5% by weight of the total composition, between 0.1 and 1.0% by weight of the total composition and 0.1 and 0.5% by weight of the total composition.

### Claim 15 (depends on 1)

The composition of claim 1, wherein the composition further comprises TiO2.

### Claim 16 (depends on 15)

The composition of claim 15, wherein the TiO2 is present in the composition at a level in a range selected from the group consisting of between 0.1 and 15% by weight of the composition, between 0.1 and 10% by weight of the composition, between 0.1 and 5% by weight of the composition and between 0.1 and 2% by weight of the composition.

### Claim 17 (depends on 1)

A film manufactured from the composition of claim 1.

### Claim 18 (depends on 1)

A sheet manufactured from the composition of claim 1.

### Claim 19 (depends on 1)

A preform manufactured from the composition of claim 1.

### Claim 20 (depends on 19)

A biaxially oriented container manufactured from the preform of claim 19.
