IP Library Granted Patent US 9,617,375
Granted Patent B2
US 9,617,375 · App. 14/403,554 · Granted Apr 11, 2017

Oxygen scavenging copolymers made from cyclic aliphatic monomers

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Quick Facts
Patent No.
US 9,617,375
App. No.
14/403,554
Granted
Apr 11, 2017
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 (19)

1. A thermoplastic compound, comprising: (a) polyethylene terephthalate matrix; and (b) a copolymer of lactide monomer and hydroxyl-terminated functionalized polybutadiene;

wherein the lactide monomer is present in the copolymer in a weight percent ranging from about 30% to about 70% of the copolymer and wherein the hydroxyl-terminated functionalized polybutadiene is present in the copolymer in a weight percent ranging from about 30% to about 70% of the copolymer; and

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 compound of claim 1 , further comprising a catalyst for the copolymer functioning as a reducing agent for oxygen molecules.

3. The compound of claim 1 , further comprising a functional additive selected from the group consisting of adhesion promoters; biocides, 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.

4. The compound of claim 1 , wherein the copolymer comprises from about 0.1 to about 3 percent by weight of the compound.

5. The compound of claim 1 , wherein the compound is in the form of a thermoplastic article.

6. The compound of claim 5 , wherein the article is a bottle pre-form.

7. The compound of claim 5 , wherein the article is a blow-molded bottle.

8. The compound of claim 7 , wherein the bottle contains a perishable food or beverage susceptible to oxidation.

9. 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 lactide monomer and hydroxyl-terminated functionalized polybutadiene, and

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

wherein the lactide monomer is present in the copolymer in a weight percent ranging from about 30% to about 70% of the copolymer and wherein the hydroxyl-terminated functionalized polybutadiene is present in the copolymer in a weight percent ranging from about 30% to about 70% of the copolymer; and

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.

10. The method of claim 9 , wherein step (a) also includes mixing a catalyst into the thermoplastic compound.

11. The method of claim 9 , wherein the copolymer reduces an oxygen molecule by reaction with a carbon-carbon unsaturated bond, thereby scavenging the oxygen molecule from the article.

Assignments (8)
RELEASE OF SECURITY INTERESTS IN PATENTS RECORDED AT REEL 037101, FRAME 0448. Recorded Jun 24, 2025
From: WELLS FARGO CAPITAL FINANCE, LLC, AS ADMINISTRATIVE AGENT
To: AVIENT CORPORATION (F/K/A POLYONE CORPORATION); COLORMATRIX HOLDINGS, INC.
Reel/Frame 071730/0746 →
CHANGE OF NAME Recorded Jul 13, 2020
From: POLYONE CORPORATION
To: AVIENT CORPORATION
Reel/Frame 053197/0141 →
RELEASE OF SECURITY INTEREST IN PATENTS AT REEL/FRAME 037113/0144 Recorded Mar 23, 2018
From: U.S. BANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: POLYONE CORPORATION; COLORMATRIX HOLDINGS, INC.
Reel/Frame 045680/0342 →
CORRECTIVE ASSIGNMENT TO CORRECT THE INCORRECT APPLICATION NUMBER 14/501,050 PREVIOUSLY RECORDED ON REEL 037101 FRAME 0448. ASSIGNOR(S) HEREBY CONFIRMS THE PATENT SECURITY AGREEMENT. Recorded Jan 27, 2016
From: POLYONE CORPORATION; COLORMATRIX HOLDINGS, INC.; POLYONE DESIGNED STRUCTURES AND SOLUTIONS LLC
To: WELLS FARGO CAPITAL FINANCE, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 037603/0208 →
CORRECTIVE ASSIGNMENT TO CORRECT THE INCORRECT APPL. NO. 14/501,050 PREVIOUSLY RECORDED AT REEL: 037113 FRAME: 0144. ASSIGNOR(S) HEREBY CONFIRMS THE SECURITY AGREEMENT. Recorded Jan 7, 2016
From: POLYONE CORPORATION; COLORMATRIX HOLDINGS, INC.; POLYONE DESIGNED STRUCTURES AND SOLUTIONS LLC
To: U.S. BANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 037508/0012 →
SECURITY AGREEMENT Recorded Nov 19, 2015
From: POLYONE CORPORATION; COLORMATRIX GROUP, INC.; COLORMATRIX HOLDINGS, INC.; THE COLORMATRIX CORPORATION; GAYSON SILICONE DISPERSIONS, INC.; POLYONE DESIGNED STRUCTURES AND SOLUTIONS LLC
To: CITIBANK, N.A,, AS ADMINISTRATIVE AGENT
Reel/Frame 037146/0724 →
PATENT SECURITY AGREEMENT Recorded Nov 16, 2015
From: POLYONE CORPORATION; COLORMATRIX HOLDINGS, INC.; POLYONE DESIGNED STRUCTURES AND SOLUTIONS LLC
To: U.S. BANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 037113/0144 →
SECURITY INTEREST Recorded Nov 12, 2015
From: POLYONE CORPORATION; COLORMATRIX HOLDINGS, INC.; POLYONE DESIGNED STRUCTURES AND SOLUTIONS LLC
To: WELLS FARGO CAPITAL FINANCE, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 037101/0448 →