Resinate Materials Group, Inc.

Resinate Technologies, Inc.

Eric David Vrabel

Rick Tabor

Matthew James Beatty

Kevin Anthony Rogers

Shakti L Mukerjee

Jack Rogers Kovsky

Adam William Emerson

Matthew Thomas Brown

Michael Robert Christy

Michael D Kellerman

Gary E Spilman

Woo-Sung Bae

Brian Douglas Phillips

Daniel James Seyer

Kristopher M Felice

Kyle Harris McGrath

Gage Fryz

Mickey Kellerman

Brian T Comstock-Reid

Brian Chermside

Mickey Kellermann

Rick L Tabor

Matthew J Beatty

Polyester polyols, processes for making them, and applications for the polyols are disclosed. Some of the polyols comprise recurring units from a digested thermoplastic polyester (e.g., recycled polyethylene terephthalate), a diol, an optional hydrophobe, and a clarifier. The clarifier, which in some cases is a bisphenol, bisphenol alkoxylate, bisphenol polycarbonate, sulfonyl diphenol, or sulfonyl diphenol alkoxylate, helps the polyol remain clear for weeks or months after its preparation. In some aspects, the clarifier is a monophenol, bisphenol, or poly-phenol having two or more phenylene rings wherein at least two of the phenylene rings lack a common molecular axis. The clarifier may also be an alkylated phenol, an epoxy resin, an epoxy novolac resin, a diphenylmethane, or a tris(aryloxy)phosphate. The polyols are valuable for formulating a variety of polyurethanes and related products&#x2014;including polyurethane dispersions, flexible and rigid foams, coatings, adhesives, sealants, and elastomers&#x2014;and they provide a sustainable alternative to bio- or petrochemical-based polyols.

Polyester polyols with increased clarity

The present invention relates to coatings, particularly high performance coatings, containing a polyester polyol comprising recurring units derived from a polyacid source, poly(bisphenol-A carbonate) (PBAC), and a glycol. The PBAC is preferably recycled poly(bisphenol-A carbonate) (rPBAC). These coatings provide improved salt spray and stain resistance along with a variety of other coating performance attributes. The polyols can contain a significant recycle and biobased content, making them sustainable alternatives to petroleum based polyols.

High performance coatings

Polyester polyols made from thermoplastic polyesters are disclosed. The polyols can be made by heating a thermoplastic polyester such as virgin PET, recycled PET, or mixtures thereof, with a glycol to give a digested intermediate, which is then condensed with a dimer fatty acid to give the polyol. The invention includes a polyester polyol comprising recurring units of a glycol-digested thermoplastic polyester and a dimer fatty acid. The polyester polyol can also be made in a single step by reacting the thermoplastic polyester, glycol, and dimer acid under conditions effective to produce the polyol. High-recycle-content polyols having desirable properties and attributes for formulating polyurethane products, including aqueous polyurethane dispersions, can be made. The polyols provide a sustainable alternative to bio- or petrochemical-based polyols.

Polyester polyols from thermoplastic polyesters and dimer fatty acids

Polyester polyols made from thermoplastic polyesters are disclosed. The polyols are reaction products of a thermoplastic polyester, a glycol, and a hydrophobe selected from ricinoleic acid, ethoxylated castor oil, saturated or unsaturated C-Cdicarboxylic acids, tung oil, soybean oil, sunflower oil, cardanol-based products, recycled cooking oil, isostearyl alcohol, hydroxy-functional materials derived from epoxidized, ozonized, or hydroformylated fatty esters or fatty acids, and mixtures thereof. In one process, the polyols are made by reacting the thermoplastic polyester with a glycol to give a digested intermediate, which is then reacted with the hydrophobe. In another process, the thermoplastic polyester, glycol, and hydrophobe are combined and reacted in a single step. These hydrophobes facilitate the production from recycled thermoplastics of polyols that have good transparency and little or no particulate settling or phase separation. High-recycle-content polyols having desirable properties and attributes for formulating polyurethane products, including aqueous polyurethane dispersions, can be made. The polyols provide a sustainable alternative to bio- or petrochemical-based polyols.

High recycle content polyester polyols

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 C-Cfatty acid units, saturated or unsaturated C-Cfatty acids, alkoxylated castor oil, saturated or unsaturated C-Cdicarboxylic acids or diols, cardanol-based products, recycled cooking oil, branched or linear C-Cfatty alcohols, hydroxy-functional materials derived from epoxidized, ozonized, or hydroformylated fatty esters or acids, or mixtures thereof.

Integrated process for treating recycled streams of PET and PTT

Polyester polyols made from recycled polyethylene terephthalate (rPET) and processes for making them are disclosed. The rPET is heated with a C-Cglycol reactant to give a digested intermediate comprising glycols and a terephthalate component, which comprises 45 to 70 wt. % of bis(hydroxyalkyl)terephthalates, and preferably lesser amounts of terephthalate dimers and trimers. Treatment of the digested intermediate with activated carbon gives a polyester polyol having a color index less than 20. The polyols have desirable hydroxyl numbers, viscosities, appearance, and other attributes for formulating polyurethane products and are a sustainable alternative to bio- or petrochemical-based polyols.

Recycle-content polyester polyols

Cycloaliphatic polyester polyols and processes for making them from thermoplastic polyesters are disclosed. One process comprises heating a thermoplastic polyester with a glycol to give a digested intermediate and hydrogenating aromatic rings in the digested intermediate to produce the cycloaliphatic polyester polyol. Optionally, the digested intermediate is reacted with a hydrophobe to give a modified polyol prior to hydrogenation, and the modified polyol is hydrogenated to give the cycloaliphatic polyester polyol. The high-recycle-content cycloaliphatic polyester polyols have desirable attributes for formulating polyurethane dispersions, two-component polyurethane coatings, mono- or poly(meth)acrylates, polyisocyanurates, flexible and rigid foams, coatings, adhesives, sealants, and elastomers, and they provide a sustainable alternative to petrochemical-based polyols.

Cycloaliphatic polyester polyols from thermoplastic polyesters

The present invention relates to the chemical digestion of keratin, such as avian feathers and wool. The digestion product is made by heating the feathers or wool with a solvent selected from glycols, alkanolamines, polyamines, and combinations thereof. The resulting digested keratin product is a keratin-derived polyol useful for making polymeric materials such as polyurethanes. The digestion products provide a sustainable alternative to petrochemical based intermediates.

Digestion of keratin

The present invention relates to polyester polyols made from aromatic polyacid sources such as thermoplastic polyesters. The polyols can be made by heating a thermoplastic polyester such as virgin polyethylene terephthalate, recycled polyethylene terephthalate, or mixtures thereof, with a glycol to give a digested intermediate which is then reacted with a digestible polymer, which can be obtained from various recycle waste streams. The polyester polyols comprise a glycol-digested polyacid source and a further digestible polymer. The polyester polyols provide a sustainable alternative to petrochemical or biochemical based polyester polyols.

Polyester polyols from recycled polymers and waste streams

The presently disclosed and/or claimed inventive concept(s) relates generally to oligomeric reaction products formed by the depolymerization of polyethylene terephthalate polymers and methods thereof. More specifically, the presently disclosed and/or claimed inventive concept(s) relates to oligomeric reaction products formed by the depolymerization of polyethylene terephthalate polymer obtained from, for example but not by way of limitation, waste products, such as beverage containers made from polyethylene terephthalate (PET). The oligomeric reaction products can, in one embodiment, be used as a starting material for polyurethanes. The presently disclosed and/or claimed inventive concept(s) also relates to processes for producing oligomeric reaction products from the depolymerization of polyethylene terephthalate. More particularly, the presently disclosed and/or claimed inventive concept(s) relates to a process of producing oligomeric reaction products of polyethylene terephthalate capable of controlling the removal of byproducts during the reaction. The presently disclosed and/or claimed inventive concept(s) also relates to ultraviolet curable urethane acrylate and polyethylene terephthalate compositions and methods of making and uses thereof.

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Ferndale, MI, United States of America

Eric David Vrabel