# US 10,308,785 B2 · Integrated process for treating recycled streams of PET and PTT

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- Number: US 10,308,785 B2
- Document ID: US10308785B2
- Status: Granted
- Kind: B2
- Application number: 15/497,288
- Filed: 2017-04-26
- Published: 2017-08-10
- Granted: 2019-06-04
- Earliest claimed: 2015-01-30
- Assignees: Resinate Materials Group, Inc.
- Applicants: Resinate Materials Group, Inc.
- Inventors: Rick Tabor; Shakti L. Mukerjee; Kevin Anthony Rogers; Eric David Vrabel; Brian Chermside; Adam W. Emerson; Brian Douglas Phillips
- Web page: https://patentgrep.com/patent/US10308785B2

## CPC

- C08J 11/24: containing hydroxyl groups
- C08G 18/0823: {containing carboxylate salt groups or groups forming them}
- C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G 18/36: Hydroxylated esters of higher fatty acids
- C08G 18/42: Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G 18/4288: {modified by higher fatty oils or their acids or by resin acids}
- C08G 18/7664: {containing alkylene polyphenyl groups}
- C08G 63/00: Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule (polyester-amides C08G69/44; polyester-imides C08G73/16)
- C08G 63/16: Dicarboxylic acids and dihydroxy compounds
- C08G 63/916: {Dicarboxylic acids and dihydroxy compounds}
- C08K 5/12: of cyclic polycarboxylic acids
- C08J 2367/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds; (C08J2367/06 takes precedence)
- C08J 2375/04: Polyurethanes
- C08J 2375/06: from polyesters
- C08J 2423/02: not modified by chemical after treatment
- C08J 2467/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08J2467/06 takes precedence)
- C08J 2475/04: Polyurethanes
- Y02P 20/10: Process efficiency
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A process for producing a polyester polyol comprising reacting a recycle stream selected from recycled PET carpet, carpet fiber, containers, textiles, articles or mixtures thereof, with a glycol in a reactor, thereby forming a digested product stream comprising polyols, and an undigested stream; and then reacting the digested product stream with a hydrophobe selected from dimer fatty acids, trimer fatty acids, oleic acid, ricinoleic acid, tung oil, corn oil, canola oil, soybean oil, sunflower oil, bacterial oil, yeast oil, algae oil, castor oil, triglycerides or alkyl carboxylate esters having saturated or unsaturated C6-C36 fatty acid units, saturated or unsaturated C6-C36 fatty acids, alkoxylated castor oil, saturated or unsaturated C9-C18 dicarboxylic acids or diols, cardanol-based products, recycled cooking oil, branched or linear C6-C36 fatty alcohols, hydroxy-functional materials derived from epoxidized, ozonized, or hydroformylated fatty esters or acids, or mixtures thereof.

## Claims

### Claim 1

A process comprising reacting
(a.) polyethylene terephthalate or polytrimethylene terephthalate;
(b.) polyurethane flexible foam; and
(c.) a glycol
in a reactor comprising a mixer, thereby forming a completely digested intermediate stream comprising a polyol and an undigested stream comprising contaminants;
separating the undigested stream from the completely digested intermediate, thereby forming a separated digested intermediate stream; and
reacting the digested intermediate stream with a hydrophobe selected from oleic acid, ricinoleic acid, tung oil, corn oil, canola oil, soybean oil, sunflower oil, bacterial oil, yeast oil, algae oil, castor oil, triglycerides or alkyl carboxylate esters having saturated or unsaturated C6-C36 fatty acid units, saturated or unsaturated C6-C36 fatty acids, alkoxylated castor oil, saturated or unsaturated C9-C18 dicarboxylic acids or diols, cardanol-based products, recycled cooking oil, branched or linear C6-C36 fatty alcohols, hydroxy-functional materials derived from epoxidized, ozonized, or hydroformylated fatty esters or acids, or mixtures thereof.

### Claim 2 (depends on 1)

The process of claim 1, wherein the polyethylene terephthalate or polytrimethylene terephthalate are selected from recycled PET or PTT-based carpet fibers, recycled PET bottle bale material, recycled PET or PTT fabric or fibers, or mixtures thereof.

### Claim 3 (depends on 1)

The process of claim 1, wherein the PET or PTT-based carpet fibers or mixtures thereof have been densified.

### Claim 4 (depends on 1)

The process of claim 1, wherein the digested product stream is further reacted with a C3-C8 dicarboxylic acids, their mono or dialkyl esters, mono or dialkenyl esters, or anhydrides, thereby forming a polyester polyol.

### Claim 5 (depends on 1)

The process of claim 1, wherein the digested product stream is further reacted with an amine scavenger such as a glycidyl ether, epoxide or isocyanate.

### Claim 6 (depends on 1)

The process of claim 1, wherein the flexible polyurethane foam comprises recycled flexible polyurethane foam rebond carpet underlay or recycled flexible polyurethane foam carpet underlay.
