OXYGEN SCAVENGING COPOLYMERS MADE FROM CYCLIC ALIPHATIC MONOMERS

• US 20150105486A1
• Filed: 05/22/2013
• Published: 04/16/2015
• Est. Priority Date: 05/25/2012
• Status: Active Grant

• Current Assignee: Avient Corp.
• Original Assignee: Polyone Corporation (Avient Corp.)
• Inventors: Hu, Ling, Avakian, Roger W.
• Granted Patent: US 9,617,375 B2
• Time in Patent Office: Days
• US Class Current: 521/140
• CPC Class Codes: B65D 81/266 for absorbing gases, e.g. oxygen absorbers or desiccants B65D51/244, B65D51/30 take precedence
• CPC Class Codes: B65D 81/28 Applications of food preservatives, fungicides, pesticides or animal repellants
• CPC Class Codes: B65D 85/70 for materials not otherwise provided for
• CPC Class Codes: C08G 2390/00 Containers
• CPC Class Codes: C08G 63/08 Lactones or lactides
• CPC Class Codes: C08L 2201/08 Stabilised against heat, light or radiation or oxydation
• CPC Class Codes: C08L 2203/10 used for bottles
• CPC Class Codes: C08L 67/06 Unsaturated polyesters

Abstract

A method and system for oxygen molecule scavenging is disclosed. The system employs as a novel copolymer as the reducing agent for oxygen molecules. The copolymer is the polymerization product of cyclic aliphatic monomer and unsaturated functional polymer.

Claims

1. A copolymer having carbon-carbon unsaturated bonds susceptible to reaction with oxygen molecules, comprising:

a polymerization product of cyclic aliphatic monomer and unsaturated functional polymer.

2. The copolymer of claim 1, wherein the cyclic aliphatic monomer is selected from the group consisting of lactide, glycolide, propriolactone, butyrolactone, valerolactone, caprolactone, cyclic carbonates, lactams, azlactones, and combinations thereof.

3. The copolymer of claim 1, wherein the unsaturated functional polymer is selected from the group consisting of hydroxyl-functional polyalkenes, hydroxyl-functional polyalkynes, glycidyl-functional polyalkenes or glycidyl-functional polyalkynes, and combinations thereof.

4. The copolymer of claim 1, wherein the cyclic aliphatic monomer is selected from the group consisting of lactide and epsilon-caprolactone.

5. The copolymer of claim 1, wherein the cyclic aliphatic monomer is present in the copolymer in a weight percent ranging from about 30 to about 70 of the copolymer and wherein the unsaturated functional polymer is present in the copolymer in a weight percent ranging from about 30 to about 70 of the copolymer.

6. The copolymer of claim 1, wherein the cyclic aliphatic monomer is present in the copolymer in a weight percent ranging from about 35 to about 65 of the copolymer and wherein the unsaturated functional polymer is present in the copolymer in a weight percent ranging from about 35 to about 65 of the copolymer.

7. The copolymer of claim 1, wherein the cyclic aliphatic monomer is present in the copolymer in a weight percent ranging from about 40% to about 60% of the copolymer and wherein the unsaturated functional polymer is present in the copolymer in a weight percent ranging from about 40% to about 60% of the copolymer.

8. The copolymer of claim 7, wherein the copolymer has a weight average molecular weight (Mw) of about 15,000-20,000, a number average molecular weight (Mn) of about 8,500-10,000, and a polydispersity of from about 1.8 to about 2.2, all as measured via Gel Permeation Chromatography (GPC) using polystyrene as a test reference.

9. The copolymer of claim 8, wherein the unsaturated functional polymer is hydroxyl-terminated functionalized polybutadiene.

10. A thermoplastic compound, comprising:

(a) a thermoplastic polymer matrix; and

(b) a copolymer of claim 1.

11. The compound of claim 10, further comprising a catalyst for the copolymer functioning as a reducing agent for oxygen molecules.

12. The compound of claim 10, further comprising a functional additive selected from the group consisting of adhesion promoters;

biocides (antibacterials, fungicides, and mildewcides), anti-fogging agents;

anti-static agents;

bonding, blowing and foaming agents;

dispersants;

fillers and extenders;

fire and flame retardants and smoke suppresants;

impact modifiers;

initiators;

lubricants;

micas;

pigments, colorants and dyes;

plasticizers;

processing aids;

release agents;

silanes, titanates and zirconates;

slip and anti-blocking agents;

stabilizers;

stearates;

ultraviolet light absorbers;

viscosity regulators;

waxes; and

combinations of them.

13. The compound of claim 10, wherein the copolymer comprises from about 0.1 to about 3 percent by weight of the compound.

14. The compound of claim 10, wherein the compound is in the form of a thermoplastic article.

15. The compound of claim 14, wherein the article is a bottle pre-form.

16. The compound of claim 14, wherein the article is a blow-molded bottle.

17. The compound of claim 16, wherein the bottle contains a perishable food or beverage susceptible to oxidation.

18. A method for scavenging for oxygen within a thermoplastic article, comprising:

(a) mixing a reducing agent for oxygen molecules into a thermoplastic compound and

(b) forming an article from the thermoplastic compound,

wherein the reducing agent is a copolymer of claim 1, and

wherein the copolymer has carbon-carbon unsaturated bonds susceptible to reaction with oxygen molecules.

19. The method of claim 18, wherein step (a) also includes mixing a catalyst into the thermoplastic compound.

20. The method of claim 18, wherein the copolymer reduces an oxygen molecule by reaction with a carbon-carbon unsaturated bond, thereby scavenging the oxygen molecule from the article.