Patents Assigned to Resinate Materials Group, Inc.
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Patent number: 10934390Abstract: 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.Type: GrantFiled: October 11, 2017Date of Patent: March 2, 2021Assignee: RESINATE MATERIALS GROUP, INC.Inventors: Rick Tabor, Eric D. Vrabel
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Patent number: 10745585Abstract: 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.Type: GrantFiled: September 29, 2016Date of Patent: August 18, 2020Assignee: RESINATE MATERIALS GROUP, INC.Inventors: Gary Spilman, Michael Christy, Eric Vrabel, Gage Fryz, Rick Tabor, Brian T. Comstock-Reid
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Patent number: 10662364Abstract: A drilling fluid comprising a carrier fluid, an aromatic polyester polyol and an additive selected from a thickener, a wetting agent, an emulsifier, a weighting agent, a pH control agent, a lubricant or mixtures thereof.Type: GrantFiled: March 16, 2016Date of Patent: May 26, 2020Assignee: RESINATE MATERIALS GROUP, INC.Inventors: Shakti L. Mukerjee, Kevin Anthony Rogers, Rick Tabor
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Patent number: 10611879Abstract: 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.Type: GrantFiled: April 15, 2019Date of Patent: April 7, 2020Assignee: RESINATE MATERIALS GROUP, INC.Inventors: Shakti L. Mukerjee, Rick Tabor, Adam William Emerson, Kevin Anthony Rogers, Eric D. Vrabel, Matthew T. Brown, Matthew J. Beatty, Jack Rogers Kovsky, Michael D. Kellerman, Michael Robert Christy
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Patent number: 10414859Abstract: 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 C9-C18 dicarboxylic 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.Type: GrantFiled: October 19, 2015Date of Patent: September 17, 2019Assignee: RESINATE MATERIALS GROUP, INC.Inventors: Rick Tabor, Kevin Anthony Rogers, Eric D Vrabel, Matthew James Beatty, Woo-Sung Bae, Shakti L Mukerjee
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Patent number: 10344121Abstract: 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.Type: GrantFiled: November 7, 2017Date of Patent: July 9, 2019Assignee: RESINATE MATERIALS GROUP, INC.Inventors: Shakti L. Mukerjee, Rick Tabor, Adam William Emerson, Kevin Anthony Rogers, Eric D. Vrabel, Matthew T. Brown, Matthew J. Beatty, Jack Rogers Kovsky, Michael D. Kellerman, Michael Robert Christy
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Patent number: 10336958Abstract: Sustainable lubricant compositions made from recycled thermoplastic polyesters and other reclaimed or biorenewable reactants and a method of formulating them are disclosed. The lubricant compositions comprise a polyester base oil, which incorporates recurring units from a digested thermoplastic polyester, a low-molecular-weight polyol, and C8-C24 fatty acid. The base oil has a number-average molecular weight within the range of 300 to 5000 g/mol, a hydroxyl value less than 50 mg KOH/g, and a viscosity at 40° C. less than 5000 cSt. Some of the lubricant compositions comprise the polyester base oil and one or more additives including anti-wear agents, corrosion inhibitors, antioxidants, thickeners, detergents, and the like.Type: GrantFiled: August 25, 2017Date of Patent: July 2, 2019Assignee: RESINATE MATERIALS GROUP, INC.Inventors: Woo-Sung Bae, Jack R. Kovsky, Rick Tabor
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Patent number: 10336925Abstract: Semi-crystalline polyester polyols and their use in reactive hot-melt adhesives are disclosed. The polyols comprise recurring units of a C2-C10 aliphatic diol, a C8-C24 aliphatic dicarboxylic acid, and 1 to 20 wt. % of an aromatic dicarboxylic acid source, a polycarbonate, or a combination thereof. The polyols have a hydroxyl number within the range of 14 to 112 mg KOH/g. Reactive hot-melt adhesives from the polyols and composite structures produced using the adhesives are also disclosed. A minor proportion of aromatic dicarboxylic acid, polycarbonate content in the polyester polyol surprisingly improves the properties of reactive hot-melt adhesives when compared with a commercial hot-melt adhesive or an adhesive formulated using an all-aliphatic polyester polyol. The adhesives are useful for bonding a wide variety of substrates, including paper, wood, glass, ceramics, plastics, and metals.Type: GrantFiled: September 6, 2016Date of Patent: July 2, 2019Assignee: RESINATE MATERIALS GROUP, INC.Inventors: Woo-Sung Bae, Kevin Rogers, Michael Christy, Rick Tabor
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Patent number: 10308785Abstract: 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.Type: GrantFiled: April 26, 2017Date of Patent: June 4, 2019Assignee: RESINATE MATERIALS GROUP, INC.Inventors: Rick Tabor, Shakti L. Mukerjee, Kevin Anthony Rogers, Eric David Vrabel, Brian Chermside, Adam W. Emerson, Brian Douglas Phillips
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Patent number: 10280277Abstract: 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.Type: GrantFiled: May 23, 2017Date of Patent: May 7, 2019Assignee: RESINATE MATERIALS GROUP, INC.Inventors: Rick Tabor, Shakti L. Mukerjee, Kevin Anthony Rogers, Adam W. Emerson, Eric David Vrabel, Brian Douglas Phillips
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Patent number: 10273332Abstract: Polyester polyols made from recycled polyethylene terephthalate (rPET) and processes for making them are disclosed. The rPET is heated with a C3-C10 glycol 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.Type: GrantFiled: April 30, 2015Date of Patent: April 30, 2019Assignee: RESINATE MATERIALS GROUP, INC.Inventors: Rick Tabor, Eric D. Vrabel, Kevin Anthony Rogers, Shakti L. Mukerjee, Matthew J. Beatty, Adam William Emerson, Matthew T. Brown, Jack Rogers Kovsky, Michael D. Kellerman, Michael Robert Christy
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Patent number: 10155837Abstract: Polyester polyol compositions are disclosed. The polyol compositions, which comprise recurring units of a digested thermoplastic polyester, a glycol, and castor oil, ricinoleic acid, or a mixture of castor oil and ricinoleic acid, have hydroxyl numbers within the range of 20 to 150 mg KOH/g and average hydroxyl functionalities within the range of 2.5 to 3.5. The invention includes flexible polyurethane foams that incorporate the polyester polyols. Sustainable polyester polyols made completely or in substantial part from recycled, post-industrial, and/or biorenewable materials such as polyethylene terephthalate, glycols, and castor oil are provided. The polyols have desirable properties for formulating flexible polyurethane foams and other products.Type: GrantFiled: August 1, 2017Date of Patent: December 18, 2018Assignee: RESINATE MATERIALS GROUP, INC.Inventors: Matt Brown, Michelle Samson, Jack R. Kovsky, Woo-Sung Bae, Shakti L. Mukerjee, Rick Tabor
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Patent number: 10040899Abstract: 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.Type: GrantFiled: November 10, 2016Date of Patent: August 7, 2018Assignee: Resinate Materials Group, Inc.Inventors: Rick Tabor, Eric David Vrabel, Matthew Beatty
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Patent number: 10030099Abstract: 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.Type: GrantFiled: March 30, 2016Date of Patent: July 24, 2018Assignee: Resinate Materials Group, Inc.Inventors: Rick Tabor, Eric David Vrabel, Matthew J Beatty, Jack Rogers Kovsky
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Patent number: 9988489Abstract: Polyester polyols, processes for making them, and applications for the polyols are disclosed. In some aspects, the polyols comprise recurring units from a thermoplastic polyester or an aromatic polyacid source, a glycol, and a lignin, tannin, or mixture thereof. Optionally, the polyols incorporate recurring units of a hydrophobe. The polyols are made in one or multiple steps; in some aspects, the thermoplastic polyester or aromatic polyacid source and the glycol are reacted first, followed by reaction with the lignin, tannin, or mixture thereof. High-recycle-content polyols having desirable properties and attributes for formulating polyurethane products, including two-component polyurethane coatings, can be made. The polyols provide a sustainable alternative to bio- or petrochemical-based polyols.Type: GrantFiled: July 31, 2017Date of Patent: June 5, 2018Assignee: Resinate Materials Group, Inc.Inventors: Shakti Mukerjee, Kevin Anthony Rogers, Matthew James Beatty, Gary E. Spilman
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Patent number: 9951171Abstract: 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.Type: GrantFiled: October 14, 2015Date of Patent: April 24, 2018Assignee: Resinate Materials Group, Inc.Inventors: Rick Tabor, Eric David Vrabel, Matthew J Beatty, Gary E. Spilman, Kevin Anthony Rogers, Michael Robert Christy, Matthew Thomas Brown, Jack Rogers Kovsky, Woo-Sung Bae, Shakti L Mukerjee
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Patent number: 9896540Abstract: 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.Type: GrantFiled: July 8, 2016Date of Patent: February 20, 2018Assignee: Resinate Materials Group, Inc.Inventors: Rick Tabor, Eric David Vrabel, Matthew J Beatty, Gary E. Spilman, Kevin Anthony Rogers, Michael Robert Christy, Matthew Thomas Brown, Jack Rogers Kovsky, Woo-Sung Bae, Shakti L Mukerjee
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Patent number: 9890243Abstract: The present invention relates to polymeric plasticizer compositions made from an aromatic acid source, a glycol, and a C4-C36 monocarboxylic acid, or ester or anhydride thereof. The aromatic acid source can include polymeric materials such as recycled polyethylene terephthalate (PET). The present invention also relates to methods for making the polymeric plasticizer compositions, to methods of plasticizing polymeric materials, and to plasticized polymeric compositions. The polymeric plasticizers are useful for plasticizing various polymers, such as thermoplastic polymers, including, for example, polyvinyl chloride (PVC). The polymeric plasticizers provide a sustainable alternative to conventional phthalate ester plasticizers, such as diisooctyl phthalate (DOP).Type: GrantFiled: January 6, 2017Date of Patent: February 13, 2018Assignee: Resinate Materials Group, Inc.Inventors: Woo-Sung Bae, Rick Tabor, Kevin Anthony Rogers, Shakti L. Mukerjee
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Patent number: 9884938Abstract: The present invention relates to polymeric plasticizer compositions made from an aromatic acid source, a glycol, and a C4-C36 monocarboxylic acid, or ester or anhydride thereof. The aromatic acid source can include polymeric materials such as recycled polyethylene terephthalate (PET). The present invention also relates to methods for making the polymeric plasticizer compositions, to methods of plasticizing polymeric materials, and to plasticized polymeric compositions. The polymeric plasticizers are useful for plasticizing various polymers, such as thermoplastic polymers, including, for example, polyvinyl chloride (PVC). The polymeric plasticizers provide a sustainable alternative to conventional phthalate ester plasticizers, such as diisooctyl phthalate (DOP).Type: GrantFiled: January 17, 2017Date of Patent: February 6, 2018Assignee: Resinate Materials Group, Inc.Inventors: Woo-Sung Bae, Rick Tabor, Kevin Anthony Rogers, Shakti L. Mukerjee
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Patent number: 9850400Abstract: 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.Type: GrantFiled: October 14, 2015Date of Patent: December 26, 2017Assignee: Resinate Materials Group, Inc.Inventors: Rick Tabor, Eric David Vrabel, Matthew J Beatty, Jack Rogers Kovsky