# US 10,119,006 B2 · Integrated process for treating recycled streams of PET and PTT

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- Number: US 10,119,006 B2
- Document ID: US10119006B2
- Status: Granted
- Kind: B2
- Application number: 15/099,794
- Filed: 2016-04-15
- Published: 2016-08-11
- Granted: 2018-11-06
- Earliest claimed: 2015-01-30
- Applicants: Resinate Materials Group, Inc.
- Inventors: Rick Tabor; Shakti L. Mukerjee; Kevin Rogers; Adam W. Emerson; Brian Douglas Phillips
- Web page: https://patentgrep.com/patent/US10119006B2

## 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 polyester polyol produced by a process comprising:
(i) forming a digested intermediate comprising a completely digested product stream and an undigested stream comprising a polyolefin by reacting a recycled PET polymer source selected from recycled PET carpet, recycled carpet fiber, recycled PET bottle bales, recycled PET textiles, other recycled PET articles or mixtures thereof with a glycol, wherein the ratio of moles glycol/moles PET is from 1.0 to 6.0;
(ii) separating the completely digested product stream from the undigested stream, thereby forming a separated digested product stream and a separated undigested product stream comprising the polyolefin component;
(iii) reacting the separated digested product stream with a hydrophobe at a ratio of moles hydrophobe/moles PET of from 0.1 to 3.0, the hydrophobe being 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, 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,
wherein the amount of the hydrophobe in the polyester polyol is 5 to 55 wt %, and the polyester polyol has a hydroxyl number of from 40 to 400 mg KOH/g.

### Claim 2 (depends on 1)

The composition of claim 1 wherein the polyester polyol has a viscosity at 50° C. greater than 10,000 cps.

### Claim 3 (depends on 1)

The polyester polyol of claim 1, wherein the undigested stream further comprises a component selected from adhesive, calcium carbonate or mixtures thereof.

### Claim 4 (depends on 1)

The polyester polyol of claim 1 wherein the ratio of moles glycol/moles PET is from 2.5 to 4.5.

### Claim 5 (depends on 1)

The polyester polyol of claim 1 further comprising a moles hydrophobe/moles PET of from 0.1 to 1.0.

### Claim 6 (depends on 1)

The polyester polyol of claim 1 wherein the hydrophobe is 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, alkoxylated castor oil, saturated or unsaturated C9-C18 dicarboxylic acids, 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 7 (depends on 1)

The polyester polyol of claim 1 further comprising:
(iv) treating the polyolefin component of step (ii) to form a processed polyolefin.

### Claim 8 (depends on 7)

The polyester polyol of claim 7 wherein the treatment of the polyolefin component comprises rinsing, drying and extrusion into fibers or pellets.

### Claim 9 (depends on 6)

The polyester polyol of claim 6 wherein the hydrophobe is selected from C9-C18 dicarboxylic acids or mixtures thereof.