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Polyester Compositions Containing Metathesis Polymers with Reduced Recycle Color

a polymer and composition technology, applied in the field of aromatic polyester compositions, can solve the problems of compositions not desirable for recycling, limited packaging life of resins, and difficulty in recycling, and achieve the effect of reducing color formation, reducing leaching or migration of rubber polymers

Inactive Publication Date: 2009-12-10
FIRESTONE POLYMERS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0081]The compositions of one or more embodiments of this invention are advantageously recyclable where formation of color is reduced. A further advantage would be expected by the reaction and attachment of the functional metathesis polymer to the aromatic polyester substantially reducing the leaching or migration of the rubber polymer away from the polyester.
[0082]In order to demonstrate the practice of the present invention, the following examples have been prepared and tested. The examples should not, however, be viewed as limiting the scope of the invention. The claims will serve to define the invention.

Problems solved by technology

These resins, however, have limited packaging life, especially in the packaging of food and beverages that are sensitive to or degrade in the presence of oxygen.
Unfortunately, the presence of these unsaturated polymers within the polyester composition leads to recycling difficulty.
Namely, these compositions are not desirable for recycling because of the formation of color during the drying cycle.
In particular, these compositions have suffered from the formation of red and yellow discoloration.

Method used

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  • Polyester Compositions Containing Metathesis Polymers with Reduced Recycle Color
  • Polyester Compositions Containing Metathesis Polymers with Reduced Recycle Color
  • Polyester Compositions Containing Metathesis Polymers with Reduced Recycle Color

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Low Molecular Weight, Telechelic Acetate-Terminated Polypentenamer

[0083]A batch mixture comprised of 1.51 kg nitrogen-purged cyclopentene and 0.087 kg of 1,4-diacetoxy-2-butene were charged into a 1-gallon volume reactor, heated to 25° C., and stirred. A solution of 0.4 g of Grubbs' 2nd generation metathesis catalyst [Aldrich] in 100 mL dry, degassed toluene (0.45 mmol, 50,000:1 olefin:Ru) was charged into the vessel. Within 25 minutes, polymerization of the monomer began to occur, and a reaction temperature increase to 78° C. was observed. The resulting cement was then stirred at a constant 40° C. temperature for an additional 1 hour. At this time, a solution of 5 mL ethyl vinyl ether in 50 mL toluene was added to the polymer solution and stirred at 40° C. in order to deactivate any residual metathesis catalyst. The resulting polymer had the following characteristics: Mn=6.3 kg / mol; Mw / Mn=1.8; trans olefin content=78%; vinyl olefin content=0%; >95% acetate terminated e...

example 2

Synthesis of Telechelic, Low Molecular Weight Cyclooctene-1,5-Cyclooctadiene Copolymer

[0086]In a 1-gallon volume stainless steel reactor, a batch mixture was charged consisting of 1185 mL (996 g, 9.0 mol) of degassed cyclooctene, 560 mL (497 g, 4.6 mol) degassed 1,5-cyclooctadiene, and 60 mL (65.5 g, 0.38 mol) degassed cis-1,4-diacetoxy-2-butene. The mixture was stirred and heated to 50° C. A solution of 0.42 g (0.50 mmol) Grubbs' 2nd generation ruthenium metathesis catalyst in 10 mL dry, degassed toluene was prepared under inert atmosphere and added to the monomer mixture. Withing 1 minute, an increase in reaction temperature began to occur, with the peak temperature reaching 114° C. within 15 minutes. The reaction was stirred for 2 hours, after which a solution of 10 mL ethyl vinyl ether in hexanes was added to deactivate the metathesis catalyst. After stirring for 30 minutes, the polymer was dropped into bottles for storage and analyzed. The product polymer was an amber colored ...

example 3

Depolymerization of High Molecular Weight Polyoctenamer to Low Molecular Weight, Telechelic Cyclooctene-1,5-Cyclooctadiene Copolymer

[0087]In a 1-gallon volume stainless steel reactor, 830 g of polyoctenamer (Degussa Vestenamer 8012) pellets (Mn=65 kg / mol; Mw / Mn=1.8; 100% octenyl unit compositioni), 470 mL (417 g, 3.85 mol)degassed 1,5-cyclooctadiene, 40 mL (43.4 g, 0.25 mol) of degassed cis-1,4-diacetoxy-2-butene, and 700 mL of degassed hexanes were charged. The heterogeneous mixture was stirred and heated to 57° C. in order to melt the solid Vestenamer polymer. A solution of 0.22 g (0.26 mmol) Grubbs' 2nd generation ruthenium catalyst in 10 mL dry, degassed toluene was prepared under an inert atmosphere and added to the contents of the reactor. The reaction was stirred for 2 hours at a constant 57° C. temperature. After this period, a solution of 5 mL ethyl vinyl ether in 100 mL hexanes was added to deactivate the metathesis catalyst. After stirring for 30 minutes, the polymer was ...

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Abstract

The present disclosure relates to aromatic polyester compositions, such as PET, comprising an unsaturated polymer prepared by metathesis polymerization having at least one or more specified terminal functional groups.

Description

[0001]This application claims the benefit of U.S. Provisional application No. 60 / 777,970, filed Mar. 1, 2006, and PCT Application No. PCT / US2007 / 005332, filed Mar. 1, 2007, which are incorporated herein by reference in their entirety.FIELD OF THE INVENTION[0002]This invention relates to aromatic polyester compositions that include unsaturated polymers prepared by metathesis polymerization.BACKGROUND OF THE INVENTION[0003]Polyester resins, such as poly(ethylene terephthalate) are commonly used to fabricate containers that are useful in food and beverage packaging. These resins, however, have limited packaging life, especially in the packaging of food and beverages that are sensitive to or degrade in the presence of oxygen.[0004]To overcome these shortcomings, these resins have been blended or reacted with unsaturated polymers such as polybutadiene.[0005]Unfortunately, the presence of these unsaturated polymers within the polyester composition leads to recycling difficulty. Namely, th...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08K3/10C08L67/00
CPCC08G61/08C08L19/006C08L23/18C08L67/06C08L2666/18C08L23/00C08F232/04C08F232/06
Inventor PAWLOW, JAMESHERGENROTHER, WILLIAMGRAVES, DAN
Owner FIRESTONE POLYMERS LLC
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