IP Library Granted Patent US 10,174,155
Granted Patent B2
US 10,174,155 · App. 15/443,189 · Granted Jan 8, 2019

Oxygen scavenging copolymers made from cyclic aliphatic monomers

Inventors: Ling Hu (Westlake, OH); Roger W. Avakian (Solon, OH)
Assignee: PolyOne Corporation
C08G63/08B65D81/266B65D81/28B65D85/70C08L67/06C08G2390/00C08L2201/08C08L2203/10
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Quick Facts
Patent No.
US 10,174,155
App. No.
15/443,189
Granted
Jan 8, 2019
Kind
B2
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 (25)

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

a reactive extrusion polymerization product of cyclic aliphatic monomer and unsaturated functional polymer wherein the cyclic aliphatic monomer is selected from the group consisting of propriolactone, butyrolactone, valerolactone, caprolactone, cyclic carbonates, lactams, azlactones, and combinations thereof; 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;

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.

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

5. The copolymer of claim 1 , wherein the unsaturated functional polymer is hydroxyl-terminated functionalized polybutadiene.

6. A thermoplastic compound, comprising: (a) a thermoplastic polymer matrix; and (b) a copolymer having carbon-carbon unsaturated bonds susceptible to reaction with oxygen molecules, wherein the copolymer comprises a reactive extrusion polymerization product of cyclic aliphatic monomer and unsaturated functional polymer wherein the cyclic aliphatic monomer is selected from the group consisting of propriolactone, butyrolactone, valerolactone, caprolactone, cyclic carbonates, lactams, azlactones, and combinations thereof;

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;

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.

7. The compound of claim 6 , further comprising a catalyst for the copolymer functioning as a reducing agent for oxygen molecules.

8. The compound of claim 6 , 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 suppressants; 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.

9. The compound of claim 6 , wherein the copolymer is present in an amount from about 0.1 to about 3 percent by weight of the compound.

10. The compound of claim 6 , wherein the compound is in the form of a thermoplastic article.

11. The compound of claim 10 , wherein the article is a bottle pre-form.

12. The compound of claim 10 , wherein the article is a blow-molded bottle.

13. The compound of claim 12 , wherein the bottle contains a perishable food or beverage susceptible to oxidation.

14. 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 having carbon-carbon unsaturated bonds susceptible to reaction with oxygen molecules, wherein the copolymer comprises a reactive extrusion polymerization product of cyclic aliphatic monomer and unsaturated functional polymer wherein the cyclic aliphatic monomer is selected from the group consisting of propriolactone, butyrolactone, valerolactone, caprolactone, cyclic carbonates, lactams, azlactones, and combinations thereof;

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;

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.

15. The method of claim 14 , wherein step (a) also includes mixing a catalyst into the thermoplastic compound.

16. The method of claim 14 , wherein the copolymer reduces an oxygen molecule by reaction with a carbon-carbon unsaturated bond, thereby scavenging the oxygen molecule from the article.

Assignments (1)
CHANGE OF NAME Recorded Jul 13, 2020
From: POLYONE CORPORATION
To: AVIENT CORPORATION
Reel/Frame 053197/0141 →
Continuity (3)
Continuation 14403554
Provisional Application 61651755 · May 25, 2012
Related Publication 20170166692A1 · Jun 15, 2017