# US 9,752,005 B2 · Integrated process for treating recycled streams of PET and PTT > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,752,005 B2 - Document ID: US9752005B2 - Status: Granted - Kind: B2 - Application number: 15/099,700 - Filed: 2016-04-15 - Published: 2016-08-11 - Granted: 2017-09-05 - Earliest claimed: 2015-01-30 - Assignees: Resinate Materials Group, Inc. - Applicants: Resinate Materials Group, Inc. - Inventors: Rick Tabor; Shakti L. Mukerjee; Kevin Rogers; Woo-Sung Bae; Adam W. Emerson; Brian Douglas Phillips - Web page: https://patentgrep.com/patent/US9752005B2 ## 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: (a) reacting a recycle stream selected from recycled PET carpet, PET carpet fiber, recycled PET containers, recycled PET textiles, other recycled PET articles, or mixtures thereof, with a glycol in a reactor, thereby forming a completely digested product stream comprising polyols, and at least one undigested stream comprising undigested materials selected from polyolefins, dyes, or inorganic fillers; (b) dispersing the undigested materials in the completely digested product stream with a mixer having a high speed, high shear impeller with a tip speed of 40 to 120 feet per second; (c) separating the at least one undigested stream from the completely digested product, thereby forming a separated digested product stream; and (d) reacting the separated digested product stream in the reactor 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-C18dicarboxylic 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, thereby forming a polyester polyol. ### Claim 2 (depends on 1) The process of claim 1 further comprising reacting in step (d) the digested product stream with a modifier selected from C3-C8 dicarboxylic acids, their mono or dialkyl esters, mono or dialkenyl esters, or anhydrides. ### Claim 3 (depends on 2) The process of claim 2 wherein the modifier is selected from glutaric acid, adipic acid, succinic acid, malonic acid, cyclohexane dicarboxylic acids, maleic acid, fumaric acid, itaconic acid, phthalic acid, 2,5-furandicarboxylic acid, isophthalic acid, the anhydrides thereof, or mixtures thereof. ### Claim 4 (depends on 1) The process of claim 1 wherein the recycle stream further comprises metals selected from magnetically susceptible material, non-magnetic metals, induction field detectable metals, or mixtures thereof. ### Claim 5 (depends on 4) The process of claim 4 further comprising separating the metals from the recycle stream in a metals separation step prior to step (a). ### Claim 6 (depends on 1) The process of claim 1 wherein the digested stream is separated from the at least one undigested stream in a solid-liquid separation. ### Claim 7 (depends on 6) The process of claim 6 wherein the solid-liquid separation is selected from filtration, centrifugation, decantation, flotation, flocculation and sedimentation or combinations thereof. ### Claim 8 (depends on 1) The process of claim 1 further comprising reacting the polyester polyol with a polyisocyanate to form a polyurethane or polyisocyanurate. ### Claim 9 (depends on 1) The process of claim 1 wherein the dispersed undigested material comprises polyolefins having a particle size range of from 100 nm to 11 cm. ### Claim 10 (depends on 1) The process of claim 1 wherein the recycle stream has been comminuted prior to step (a). ### Claim 11 (depends on 1) The process of claim 1 wherein the recycled PET containers comprise PET bottles, polyolefin caps, cap seals, label adhesives and labels. ### Claim 12 (depends on 1) The process of claim 1 wherein the recycle stream comprises recycled PET containers from unprocessed bottle bales. ### Claim 13 (depends on 1) The process of claim 1, further comprising reacting the polyester polyol with acrylic acid, methacrylic acid, acryloyl chloride or methacryloyl chloride, thereby forming an acrylate or methacrylate derivative. ### Claim 14 (depends on 1) The process of claim 1, further comprising reacting the polyester polyol with a polyisocyanate to form an isocyanate terminated prepolymer. ### Claim 15 (depends on 14) The process of claim 14 further comprising reacting the isocyanate terminated prepolymer with hydroxyethyl methacrylate or hydroxyethyl acrylate, thereby forming a urethane acrylate resin or a urethane methacrylate resin. ### Claim 16 (depends on 1) The process of claim 1 wherein the glycol is selected from ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butylene glycol, 1,3-butylene glycol, 1,4-butanediol, 2-methyl-1,3-propanediol, pentaerythritol, neopentyl glycol, glycerol, trimethylolpropane, 2,2,4,4-tetramethyl-1,3-cyclobutanediol, 3-methyl-1,5-pentanediol, 1,4-cyclohexane-dimethanol, 1,3-cyclohexanedimethanol, diethylene glycol, dipropylene glycol, triethylene glycol, 1,6-hexanediol, tripropylene glycol, tetraethylene glycol, polyethylene glycols having a number average molecular weight up to about 400 g/mol, block or random copolymers of ethylene oxide and propylene oxide, and mixtures thereof. ### Claim 17 (depends on 1) The process of claim 1 wherein the polyester polyol is reacted with a C4-C36 monocarboxylic acid, ester or anhydride, and diacid selected from succinic acid, glutaric acid, pimelic acid, suberic acid, succinic acid, pimelic acid azelaic acid, sebacic acid, adipic acid, fumaric acid, maleic acid, 1,2-cyclohexane dicarboxylic acid, 1,3-cyclohexane dicarboxylic acid, 1,4-cyclohexane dicarboxylic acid, 2,5-furan dicarboxylic acid, 1,9-nonanedioic acid, 1,9-nonenedioic acid, 1,10-decanedioic acid, 1,10-decenedioic acid, 1,11-undecanedioic acid, 1,11-undecenedioic acid, 1,18-octadecanedioic acid, 1,18-octadecenedioic acid, 1,12-dodecanedioic acid, 1,12-dodecenedioic acid, 1,14-tetradecanedioic acid, 1,14-tetradecenedioic acid, 1,16-hexadecanedioic acid, 1,16-hexadecenedioic acid, eicosenedioic acid, eicosanedioic acid, docosanedioic acid, tetracosanedioic acid, tetracosendioic acid, and combinations thereof, thereby forming a polymeric plasticizer. ### Claim 18 (depends on 1) The process of claim 1, wherein the recycle stream comprises PET containers and at least one of recycled PET carpet and recycled PET textiles.