IP Library Granted Patent US 11,713,388
Granted Patent B2
US 11,713,388 · App. 17/082,722 · Granted Aug 1, 2023

Titanium dioxide catalyzed butadiene polymer based oxygen scavenging system

Inventors: Zahra Kordjazi (Montreal, CA); Abdellah Ajji (Mont-Royal, CA)
Assignee: POLYVALOR, LIMITED PARTNERSHIP
C08L1/28B32B27/08B32B27/18B65D65/40B65D81/266C08L23/06C08L67/04B32B2250/24B32B2270/00B32B2307/7242B32B2307/7265B32B2307/74B32B2553/00C08L2207/066
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Quick Facts
Patent No.
US 11,713,388
App. No.
17/082,722
Granted
Aug 1, 2023
Kind
B2
Abstract

A composition of matter having oxygen scavenging properties comprises a blend of a base polymer, a butadiene polymer, and titanium dioxide in an amount sufficient to catalyze reaction of oxygen with the butadiene polymer. In further aspects, methods for making the compositions herein and packaging film structures comprising the compositions herein, and packaging articles formed of the same, are also provided.

Claims (41)

1. A composition of matter having oxygen scavenging properties, comprising a blend of:

a base polymer;

a hydroxyl terminated polybutadiene having a number average molecular weight (M n ) in the range of from about 500 to about 10,000; and

titanium dioxide in an amount sufficient to catalyze reaction of oxygen with the hydroxyl terminated polybutadiene, wherein the titanium dioxide is selected from the group consisting of titanium dioxide having an average particle size of 10 nanometers to 20 microns, titanium dioxide which has been subject to doping, heterogeneous systems comprising titanium dioxide in combination with other semiconductors, titanium dioxide in combination with inorganic metal nanoparticles or organic material, dye-sensitized titanium dioxide, and any combination thereof.

2. The composition of claim 1 , wherein the hydroxyl terminated polybutadiene is present in an amount of from 5 to 20 percent by weight based on the weight of the composition.

3. The composition of claim 1 , wherein the titanium dioxide is present in an amount selected from the group consisting of:

1 to 5 percent by weight based on the weight of the composition; and

1 to 5 percent by weight based on the weight of the hydroxyl terminated polybutadiene.

4. The composition of claim 1 , wherein the composition does not include a curing agent.

5. The composition of claim 1 , wherein the hydroxyl terminated polybutadiene is a liquid at room temperature.

6. The composition of claim 1 , wherein the hydroxyl terminated polybutadiene has a number average molecular weight (M n ) in the range of from 500 to 8,000.

7. The composition of claim 1 , wherein the hydroxyl terminated polybutadiene has one or both of a relatively high trans content and a relatively low vinyl content.

8. The composition of claim 7 , wherein the hydroxyl terminated polybutadiene has a trans content of about 60%, a cis content of about 20%, and a vinyl content of about 20%.

9. The composition of claim 1 , wherein the titanium dioxide is present in an amount sufficient to catalyze reaction of oxygen with the hydroxyl terminated polybutadiene wherein moisture is not necessary to activate the reaction.

10. The composition of claim 1 , wherein the titanium dioxide is present in an amount sufficient to catalyze reaction of oxygen with the hydroxyl terminated polybutadiene in the absence of direct ultraviolet radiation.

11. The composition of claim 1 , wherein the hydroxyl terminated polybutadiene has a number average molecular weight (M n ) in the range of from about 500 to about 5,000.

12. The composition of claim 1 , wherein the hydroxyl terminated polybutadiene has a number average molecular weight (M n ) in the range of from about 1,000 to about 3,000.

13. The composition of claim 1 , further comprising a UV or visible light photoinitiator.

14. The composition of claim 13 , wherein the UV or visible light photoinitiator is selected from the group consisting of benzophenone, acetophenone, valerophenone, and titanocene.

15. The composition of claim 1 , wherein the titanium dioxide is doped with a doping agent selected from the group consisting of noble metal, a transition metal, and a non-metal.

16. The composition of claim 1 , wherein the titanium dioxide is titanium dioxide having an average particle size of 10 nanometers to 20 microns.

17. The composition of claim 1 , wherein the base polymer is ethyl cellulose.

18. The composition of claim 17 , wherein the composition is in a form selected from the group consisting of a solution cast film and a fibrous mat.

19. The composition of claim 18 , wherein the composition is prepared from a solvent mixture comprising the base polymer, the hydroxyl terminated polybutadiene, the titanium dioxide, and a solvent system, wherein the solvent system is selected from the group consisting of a toluene/ethanol solvent system and an ethanol/water solvent system.

20. The composition of claim 17 , wherein the composition is prepared by a technique selected from the group consisting of solution casting and electrospinning.

21. The composition of claim 17 , wherein the composition is in the form of a fibrous mat having fibers with a diameter in the range of from about 0.3±0.1 microns to about 0.6±0.2 microns.

22. The composition of claim 17 , wherein the composition does not include a curing agent.

23. The composition of claim 1 , wherein the base polymer is a polyester.

24. The composition of claim 23 , wherein the polyester is polylactic acid (PLA).

25. The composition of claim 23 , wherein the composition is prepared by reactive melt extrusion of the polyester with the hydroxyl terminated polybutadiene and the titanium dioxide.

26. The composition of claim 1 , wherein the base polymer is a polyolefin.

27. The composition of claim 26 , wherein the polyolefin is low density polyethylene (LDPE).

28. The composition of claim 27 , further comprising a hydrocarbon wax for improving dispersion of the hydroxyl terminated polybutadiene in the low density polyethylene.

29. The composition of claim 26 , wherein the composition is prepared by melt blending.

30. The composition of claim 26 , wherein the polyolefin is linear low density polyethylene (LLDPE).

31. A packaging film structure, comprising:

an oxygen scavenging layer comprising a blend of a base polymer, a hydroxyl terminated polybutadiene having a number average molecular weight (M n ) in the range of from about 500 to about 10,000, and titanium dioxide in an amount sufficient to catalyze reaction of oxygen with the hydroxyl terminated polybutadiene, wherein the titanium dioxide is selected from the group consisting of titanium dioxide having an average particle size of 10 nanometers to 20 microns, titanium dioxide which has been subject to doping, heterogeneous systems comprising titanium dioxide in combination with other semiconductors, titanium dioxide in combination with inorganic metal nanoparticles or organic material, dye-sensitized titanium dioxide, and any combination thereof.

32. The packaging film structure of claim 31 , further comprising one or both of an outer layer and a heat sealant layer.

33. The packaging film structure of claim 32 , wherein one or both of the outer layer and a heat sealant layer comprises the base polymer.

34. The packaging film structure of claim 31 , further comprising a barrier layer selected from a gas barrier layer and a moisture barrier layer.

35. The packaging film structure of claim 31 , wherein the titanium dioxide is titanium dioxide having an average particle size of 10 nanometers to 20 microns.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Mar 6, 2026
From: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION (AS SUCCESSOR IN INTEREST TO U.S. BANK NATIONAL ASSOCIATION), AS COLLATERAL AGENT
To: AMPAC FLEXIBLES, LLC; AMPAC FLEXICON, LLC; AMPAC HOLDCO, INC.; AMPAC HOLDINGS, LLC; AMPAC MOBILE HOLDINGS, LLC; AMPAC PACKAGING, LLC; AMPAC PAPER, LLC; AMPAC PLASTICS, LLC; BONITA PACKAGING PRODUCTS, INC.; CEI HOLDINGS, LLC; COATING EXCELLENCE INTERNATIONAL, LLC; GATEWAY PACKAGING COMPANY LLC; JEN-COAT, INC.; MOHAWK NORTHERN PLASTICS, LLC; POLYFIRST PACKAGING, INC.; PROAMPAC HOLDINGS INC.; PROAMPAC ORLANDO INC.; PROAMPAC PG BORROWER LLC; PROAMPAC PG INTERMEDIATE LLC; PROAMPAC REAL ESTATE HOLDINGS LLC; PROAMPAC ROCHESTER LLC; PROLAMINA CORPORATION; PROLAMINA MIDWEST CORPORATION; TRINITY PACKAGING CORPORATION; TULSACK LLC; TWISTED PAPER PRODUCTS, INC.; VITEX PACKAGING, INC.; PAC WORLDWIDE CORPORATION
Reel/Frame 075021/0794 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 9, 2022
From: AJJI, ABDELLAH; KORDJAZI, ZAHRA
To: CORPORATION DE L'ÉCOLE POLYTECHNIQUE DE MONTRÉAL
Reel/Frame 061353/0432 →
SECURITY INTEREST Recorded Jan 27, 2021
From: AMPAC FLEXIBLES, LLC; AMPAC FLEXICON, LLC; AMPAC HOLDCO, INC.; AMPAC HOLDINGS, LLC; AMPAC MOBILE HOLDINGS, LLC; AMPAC PACKAGING, LLC; AMPAC PAPER, LLC; AMPAC PLASTICS, LLC; BONITA PACKAGING PRODUCTS, INC.; CEI HOLDINGS, LLC; COATING EXCELLENCE INTERNATIONAL, LLC; GATEWAY PACKAGING COMPANY LLC; JEN-COAT, INC.; MOHAWK NORTHERN PLASTICS, LLC; POLYFIRST PACKAGING, INC.; PROAMPAC HOLDINGS INC.; PROAMPAC ORLANDO INC.; PROAMPAC PG BORROWER LLC; PROAMPAC PG INTERMEDIATE LLC; PROAMPAC REAL ESTATE HOLDINGS LLC; PROAMPAC ROCHESTER LLC; PROLAMINA CORPORATION; PROLAMINA MIDWEST CORPORATION; TRINITY PACKAGING CORPORATION; TULSACK LLC; TWISTED PAPER PRODUCTS, INC.; VITEX PACKAGING, INC.
To: U.S. BANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 055139/0731 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 8, 2020
From: CORPORATION DE L'ÉCOLE POLYTECHNIQUE DE MONTRÉAL
To: POLYVALOR, LIMITED PARTNERSHIP
Reel/Frame 054578/0215 →