# US 12,006,397 B2 · Composition comprising a polyester-polyether polymer, a transition metal catalyst, and an active material

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- Number: US 12,006,397 B2
- Document ID: US12006397B2
- Status: Granted
- Kind: B2
- Application number: 17/259,604
- Filed: 2019-07-08
- Published: 2021-10-14
- Granted: 2024-06-11
- Earliest claimed: 2018-07-13
- Assignees: Avient Switzerland GmbH
- Applicants: Clariant Plastics & Coatings Ltd
- Inventors: Bernardo Romeo; Sarah Boukobza
- Web page: https://patentgrep.com/patent/US12006397B2

## CPC

- C08G 63/672: Dicarboxylic acids and dihydroxy compounds
- C08L 67/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence)
- B01J 31/12: containing organo-metallic compounds or metal hydrides
- C08G 63/20: Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
- C08K 5/0091: {Complexes with metal-heteroatom-bonds}
- C08L 67/025: {containing polyether sequences}
- C08K 5/098: Metal salts of carboxylic acids
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

Polymer compositions with an end-capped polyether-polyester copolymer, a transition metal catalyst and an active material that acts on, interacts or reacts with moisture. The polyether-polyester copolymer has (i) polyether segments where at least one polyether segment contains at least one polytetramethylene oxide segment; (ii) polyester segments; (iii) bridging elements of the structure —CO—R2-CO—, where R2 represents an optionally substituted bivalent hydrocarbon residue consisting of 1 to 100 carbon atoms; and (iv) one or two end-caps R1-O—(C2-C4-O—)e-*, where R1 is an optionally substituted hydrocarbon residue and e is an integer of from 0 to 1000. The polymer composition is capable of scavenging oxygen and can be used in compositions and articles to remove oxygen or to function as an active oxygen barrier.

## Claims

### Claim 1

A polymer composition, comprising:
a polyether-polyester copolymer in a form of a powder having a mass median diameter D50 of less than 1000 μm,
a transition metal catalyst, and
a desiccant comprising one or more of a silica gel, a zeolite, a desiccant clay, an activated carbon, an alkali metal salt, an alkaline earth metal salt, and mixtures thereof in an amount of 0.1 wt.-% or more,
wherein the polyether-polyester copolymer comprises:
polyether segments wherein at least one polyether segment contains at least one polytetramethylene oxide segment;
(ii) polyester segments;
(iii) bridging elements of the structure —CO—R2-CO—, wherein R2 represents an optionally substituted bivalent hydrocarbon residue consisting of 1 to 100 carbon atoms; and
(iv) one or two end-caps having a formula selected from:
wherein the different monomers are distributed randomly, in blocks, or in a combination of random and block, and
R1 is an optionally substituted aliphatic hydrocarbon residue of 1 to 24 carbon atoms, an optionally substituted olefinic hydrocarbon residue of 2 to 24 carbon atoms, or an optionally substituted aromatic hydrocarbon residue of 6 to 14 carbon atoms;
said hydrocarbon residues are optionally substituted with one or more groups independently selected from the group consisting of C1-C5-alkoxy, nitro, cyano, sulfo, and combinations thereof;
b is an integer between 1 and 250;
a is an integer between 1 and 250; and
c is an integer between 1 and 70.

### Claim 2 (depends on 1)

The polymer composition of claim 1, wherein the polyether segments (i) further comprise ethylene oxide segments, propylene oxide segments or a combination thereof.

### Claim 3 (depends on 1)

The polymer composition of claim 1, wherein the polyester segments (ii) are represented by formula (II):
wherein
* represents a bond to a bridging element (iii),
R2 and R3 independently of each other represent an optionally substituted hydrocarbon residue consisting of 1 to 100 carbon atoms, and
u is an integer between 1 and 50;
wherein said hydrocarbon residues are optionally substituted with one or more groups independently selected from the group consisting of C1-5-alkoxy, nitro, cyano, sulfo, and combinations thereof.

### Claim 4 (depends on 1)

The polymer composition of claim 1, wherein bridging elements are described by formula (III)
wherein R2 represents an optionally substituted hydrocarbon residue consisting of 1 to 100 carbon atoms, and said hydrocarbon residue is optionally substituted with one or more groups independently selected from the group consisting of C1-5-alkoxy, nitro, cyano, sulfo, and combinations thereof.

### Claim 5 (depends on 1)

The polymer composition of claim 1, wherein R1 denotes methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, sec-pentyl, neo-pentyl, 1,2-dimethylpropyl, iso-amyl, n-hexyl, sec-hexyl, n-heptyl, n-octyl, 2-ethyl-hexyl, n-nonyl, n-decyl, tridecyl, isotridecyl, tetradecyl, hexadecyl, octadecyl, methylphenyl cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, or cyclodecyl.

### Claim 6 (depends on 1)

The polymer composition of claim 1, wherein the polyether-polyester copolymer has a number average of the molecular weight of between 2,000 and 1,000,000 g/mol.

### Claim 7 (depends on 1)

The polymer composition of claim 1, wherein the polyether-polyester copolymer has a mass ratio Q defined as the mass ratio between the poly(tetramethyleneoxide) content and the overall content of all dicarbonyl structure elements (ii) and (iii) of between 0.1 and 10.

### Claim 8 (depends on 1)

The polymer composition of claim 1, wherein the polyether-polyester copolymer has a mass ratio Θ defined as the mass ratio between the endcap content and the overall content of all dicarbonyl structure elements (ii) and (iii) of between 0.001 and 100.

### Claim 9 (depends on 1)

The polymer composition of claim 1, wherein the transition metal catalyst is a salt of a transition metal selected from the 1st, 2nd, or 3rd transition series of the periodic table of elements.

### Claim 10 (depends on 1)

The polymer composition of claim 1, wherein the transition metal catalyst is a salt of iron (II or III), nickel (II or III), manganese (II or III), or cobalt (II or III).

### Claim 11 (depends on 1)

The polymer composition of claim 1, wherein the transition metal catalyst is a salt selected from the group consisting of cobalt oleate, cobalt propionate, cobalt stearate, and cobalt neodecanoate.

### Claim 12 (depends on 1)

The polymer composition of claim 1, wherein the transition metal catalyst is present in an amount of 0.01 wt.-% to 5 wt.-%, based on the total weight of the polymer composition.

### Claim 13 (depends on 1)

The polymer composition of claim 1, wherein the polyether-polyester copolymer is present in amount of 5-50 wt.-%, the transition metal catalyst is present in an amount of 0.01-5 wt.-%, and the desiccant is present in an amount of 0.1-95 wt.-%, based on the total weight of the polymer composition.

### Claim 14 (depends on 1)

An active oxygen barrier composition comprising the polymer composition of claim 1.

### Claim 15 (depends on 1)

A plastic material comprising:
a thermoplastic polymer; and
the polymer composition of claim 1.

### Claim 16 (depends on 15)

A masterbatch comprising the plastic material of claim 15.

### Claim 17 (depends on 1)

An article of manufacture comprising the polymer composition of claim 1.

### Claim 18 (depends on 17)

The article of manufacture of claim 17, wherein the article of manufacture is a medical or pharmaceutical packaging element.

### Claim 19 (depends on 1)

The polymer composition of claim 1, wherein the transition metal catalyst is present in an amount of 0.07 wt.-% to 2.5 wt.-%, based on the total weight of the polymer composition.

### Claim 20 (depends on 1)

The polymer composition of claim 1, wherein the desiccant is present in an amount of 40-80 wt.-%.