IP Library Granted Patent US 9,410,014
Granted Patent B2
US 9,410,014 · App. 13/931,106 · Granted Aug 9, 2016

Polymer manufacturing process

Inventor: Robert Keith Salsman (Hoschton, GA)
C08G63/916C08G18/30C08G18/4252C09D5/02C09D5/03C09D11/30C08G2101/0008C08G2101/0083
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Quick Facts
Patent No.
US 9,410,014
App. No.
13/931,106
Granted
Aug 9, 2016
Kind
B2
Abstract

Embodiments relate to a relatively rapid transesterification process including transesterifying condensation polymers such as polyethylene terephthalate (PET), or other polyesters used in commerce, with a modifying monomer mix containing other monomers to manufacture new polymers containing the pre-condensed moieties. The process preferably only involves transesterification as a reaction mechanism. The process preferably produces a rapid buildup of molecular weight and/or polymer uniformity by the high temperature transesterification of the condensation polymer with the modifying monomer mixture. The process can be performed in any suitable vessel including an extrusion line, and it has the advantage of greatly reduced cycle times over currently used condensation polymer utilization processes such as the recycling of PET into other materials.

Claims (37)

1. A method of making a polymer comprising:

providing a condensation polyester comprising a plurality of constituent monomers and having a first molecular weight;

providing a modifying monomer selected from the group consisting of butanol, hexanol, lauryl alcohol, decanol, glycerine, trimethylolpropane, neopentyl glycol, ethylene glycol, sorbitol, pentaerythritol, cyclohexane dimethanol, stearyl alcohol, adipic acid, lauric acid, palmitic acid, stearic acid, oleic acid, behenic acid, linolenic acid, succinic acid, maleic acid, maleic anhydride acid, butanoic acid, phthalic acid, phthalic anhydride acid, isophthalic acid, terephthalic acid, trimellitic anhydride acid, diethylene glycol, triethylene glycol, polyethylene glycol 200, polyethylene glycol 400, polyethylene glycol 600, polyethylene glycol 800, polyethylene glycol 1000, ethoxylate condensates comprising 1 to 25 moles of ethylene oxide thereof, esters thereof, di-esters thereof, tri-esters thereof, amines thereof, amides thereof, and combinations thereof; and

without depolymerizing the condensation polyester into its constituent monomers, transesterifying the modifying monomer with staged addition of a predetermined amount of the condensation polyester,

wherein the transesterifying produces a final polymer having a second molecular weight that is greater than the first molecular weight.

2. The method of claim 1 , wherein the modifying monomer comprises a hydroxyl group.

3. The method of claim 1 , wherein the modifying monomer comprises an ester group.

4. The method of claim 1 , wherein the condensation polyester is polyethylene terephthalate.

5. The method of claim 1 , wherein:

the final polymer is a polyol, and

the method further comprises reacting the polyol with an isocyanate to produce a polyurethane.

6. The method of claim 1 , further comprising applying a vacuum during the transesterifying.

7. The method of claim 1 , further comprising removing ethylene glycol during the transesterifying.

8. The method of claim 1 , further comprising reacting the final polymer with an anhydride to produce an acid-terminated polymer.

9. The method of claim 1 , wherein the transesterifying is carried out at a temperature of about 150° C. to about 350° C.

10. The method of claim 1 , wherein the transesterifying is carried out at a temperature of about 200° C. to about 290° C.

11. The method of claim 1 , wherein the transesterifying is carried out for a period of less than 5 hours.

12. The method of claim 1 , wherein the condensation polyester is provided in an amount of about 30 to about 96 percent by weight of the final polymer.

13. The method of claim 1 , wherein the condensation polyester is provided in an amount of about 60 to about 80 percent by weight of the final polymer.

14. The method of claim 1 , wherein the modifying monomer is not one of the constituent monomers.

15. The method of claim 1 , further comprising:

applying the final polymer to a back of a carpet to form a carpet backing.

16. A method of making a polymer comprising:

providing polyethylene terephthalate comprising a plurality of constituent monomers and having a first molecular weight;

providing trimethylol propane; and

without depolymerizing the polyethylene terephthalate into its constituent monomers, providing a plurality of staged additions of the polyethylene terephthalate and transesterifying the trimethylol propane to produce a final polymer having a second molecular weight that is greater than the first molecular weight,

wherein the transesterifying is carried out at a temperature of about 200° C. to about 290° C. and for a period of less than 5 hours.

17. A method of making a polymer comprising:

providing a condensation polyester comprising a plurality of constituent monomers and having a first molecular weight;

providing a modifying monomer selected from the group consisting of butanol, hexanol, lauryl alcohol, decanol, glycerine, trimethylolpropane, neopentyl glycol, ethylene glycol, sorbitol, pentaerythritol, cyclohexane dimethanol, stearyl alcohol, adipic acid, lauric acid, palmitic acid, stearic acid, oleic acid, behenic acid, linolenic acid, succinic acid, maleic acid, maleic anhydride acid, butanoic acid, phthalic acid, phthalic anhydride acid, isophthalic acid, terephthalic acid, trimellitic anhydride acid, diethylene glycol, triethylene glycol, polyethylene glycol 200, polyethylene glycol 400, polyethylene glycol 600, polyethylene glycol 800, polyethylene glycol 1000, ethoxylate condensates comprising 1 to 25 moles of ethylene oxide thereof, esters thereof, di-esters thereof, tri-esters thereof, amines thereof, amides thereof, and combinations thereof; and having a molecular weight of less than 1500 Daltons; and

without depolymerizing the condensation polyester into its constituent monomers, transesterifying the modifying monomer with a predetermined amount of the condensation polyester,

wherein the transesterifying produces a final polymer having a second molecular weight that is greater than the first molecular weight.

18. A method of making a polymer consisting of:

providing a condensation polyester comprising a plurality of constituent monomers and having a first molecular weight;

providing a modifying monomer comprising more than two reactive groups; and

without depolymerizing the condensation polyester into its constituent monomers, transesterifying the modifying monomer with a predetermined amount of the condensation polyester,

wherein the transesterifying produces a final polymer having a second molecular weight that is greater than the first molecular weight.

Assignments (4)
SECURITY INTEREST Recorded Dec 22, 2017
From: ENGINEERED FLOORS, LLC
To: BRANCH BANKING AND TRUST COMPANY, AS ADMINISTRATIVE AGENT
Reel/Frame 044949/0684 →
RELEASE OF SECURITY INTEREST Recorded Nov 21, 2017
From: BANK OF AMERICA, N.A.
To: BEAULIEU GROUP, LLC
Reel/Frame 044495/0302 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2017
From: BEAULIEU GROUP, LLC
To: ENGINEERED FLOORS, LLC
Reel/Frame 044074/0091 →
SECURITY INTEREST Recorded Dec 9, 2016
From: BEAULIEU GROUP, LLC
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 040699/0372 →
Continuity (2)
Continuation 11693185 · Mar 29, 2007
Related Publication 20130289222A1 · Oct 31, 2013