Composition comprising a polyester-polyether polymer, a transition metal catalyst, and an active material

Patent metadata

Field	Value
Publication number	US-12006397-B2
Application number	US-201917259604-A
Country	US
Kind code	B2
Filing date	Jul 8, 2019
Priority date	Jul 13, 2018
Publication date	Jun 11, 2024
Grant date	Jun 11, 2024

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.

First claim

The invention claimed is:

1. A polymer composition, comprising:
a polyether-polyester copolymer in a form of a powder having a mass median diameter D 50 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 C 1 -C 5 -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.

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

3. 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 C 1-5 -alkoxy, nitro, cyano, sulfo, and combinations thereof.

4. 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 C 1-5 -alkoxy, nitro, cyano, sulfo, and combinations thereof.

5. 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.

6. 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.

7. 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.

8. 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.

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

10. 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).

11. 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.

12. 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.

13. 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.

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

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

16. A masterbatch comprising the plastic material of claim 15 .

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

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

19. 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.

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

Assignees

• Clariant Plastics & Coatings Ltd
• Avient Switzerland Gmbh

Inventors

• Romeo Bernardo
• Boukobza Sarah

Classifications

• C08L67/025

  containing polyether sequences · CPC title

• C08G63/20

  Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups · CPC title

• B01J31/12

  containing organo-metallic compounds or metal hydrides · CPC title

• C08J3/226

  using a polymer as a carrier · CPC title

• C08G63/672 Primary

  Dicarboxylic acids and dihydroxy compounds · CPC title