Patents by Inventor Karl W. Haider
Karl W. Haider has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Publication number: 20230416444Abstract: An aspartate-terminated prepolymer can be a reaction product of a reaction mixture including an aliphatic NCO-terminated prepolymer having an NCO content of from 0.5% to 15% and a number average NCO functionality of <2, and a compound according to formula (I) wherein, X represents a linear or branched aliphatic group obtained by removing amino groups from a linear or branched aliphatic polyamine, R1 and R2 are identical or different and represent organic groups which are inert towards isocyanate groups at a temperature of 100° C. or less, R3 and R4 are identical or different and represent hydrogen or organic groups which are inert towards isocyanate groups at a temperature of 100° C. or less, n represents an integer with a value of at least 2. The aliphatic NCO-terminated prepolymer can the compound according to formula I can be combined at an NCO:NH equivalent ratio of 1:1.5 to 1:5.Type: ApplicationFiled: June 23, 2022Publication date: December 28, 2023Inventors: Raymond Zeliznik, Charles A. Gambino, Karl W. Haider, Frank C. Rossitto
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Publication number: 20230356508Abstract: Provided is an adhesive comprising a reaction product of (A1) an aliphatic isocyanate having an NCO group content of 18 to 64 and (A2) a polyol or polyamine having a molecular weight of from 400 to 4000; and (B) a polyaspartate compound, wherein viscosity of the adhesive, as measured @ 23° C. according to ASTM D4212-16, remains below 60 seconds for after four hours, and wherein the adhesive develops an acceptable bond strength to a substrate, defined as having a minimum of 150 g/in. measured @ 23° C. according to ASTM D 1876-01 or substrate tear, in less than or equal to five days after the substrate is laminated with the adhesive. The adhesives are free of aromatic amines and may find use in multi-layered laminated films for the production of flexible packaging useful in a variety of industries, including the food processing, cosmetics, and detergents industries.Type: ApplicationFiled: June 27, 2023Publication date: November 9, 2023Inventors: Karl W. Haider, Raymond Zeliznik, Philip Jones, Tina Kasardo
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Publication number: 20230323169Abstract: Provided is an adhesive comprising a reaction product of (A) an aliphatic polyisocyanate having a molecular weight of from 132 to 700; and (B) a polyaspartate comprising a reaction product of (B1) a polyamine having a molecular weight of at least 240, and (B2) a Michael addition receptor, wherein viscosity @ 23° C. according to ASTM D1084-16, remains below 150 cps after four hours, and wherein the adhesive develops an acceptable bond strength to a substrate, defined as having a minimum of 150 g/in. measured @ 23° C. according to ASTM D 1876-01 or substrate tear, in less than five days after the substrate is laminated with the adhesive. The inventive flexible packaging adhesives are free of aromatic amines and may find use in multilayer laminates for a variety of industries, including the food processing, cosmetics, and detergents industries.Type: ApplicationFiled: June 15, 2023Publication date: October 12, 2023Inventors: Karl W. Haider, Raymond Zeliznik, Philip Jones
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Patent number: 11225543Abstract: In one or more embodiments, the present invention provides a novel approach to the addition of plasticizers for softening TPUs, i.e., lowering the durometer and the melt viscosity. This approach involves incorporating bonded sulfonate groups with quaternary ammonium counterions into the TPU. In one or more embodiments of the present invention, the softening of TPU is achieved by incorporating an ionic diol, such as N,N-bis (2-hydroxyethyl)-2-aminoethane-sulfonic acid (BES), coupled with various bulky alkyl ammonium cations, during the chain extension step of the TPU synthesis. It is believed that that steric hindrance of the bulky quaternary ammonium groups weakens the dipole-dipole interactions of the sulfonate groups and/or lowers the crystallinity of the hard block, thereby creating additional free volume that softens the polymer and lowers the melt viscosity.Type: GrantFiled: February 26, 2019Date of Patent: January 18, 2022Assignee: The University of AkronInventors: Matthew Becker, Robert A. Weiss, Zachary Kurtiss Zander, Don S. Wardius, Karl W. Haider, Bruce D. Lawrey
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Patent number: 11041039Abstract: In one or more embodiments, the present invention provides a novel approach to the addition of plasticizers for softening TPUs, i.e., lowering the durometer and the melt viscosity. This approach involves incorporating bonded sulfonate groups with quaternary ammonium counterions into the TPU. In one or more embodiments of the present invention, the softening of TPU is achieved by incorporating an ionic diol, such as N,N-bis (2-hydroxyethyl)-2-aminoethane-sulfonic acid (BES), coupled with various bulky alkyl ammonium cations, during the chain extension step of the TPU synthesis. It is believed that that steric hindrance of the bulky quaternary ammonium groups weakens the dipole-dipole interactions of the sulfonate groups and/or lowers the crystallinity of the hard block, thereby creating additional free volume that softens the polymer and lowers the melt viscosity.Type: GrantFiled: February 6, 2019Date of Patent: June 22, 2021Assignees: Covestro LLC, The University of AkronInventors: Matthew Becker, Robert A. Weiss, Zachary Kurtiss Zander, Don S. Wardius, Karl W. Haider, Bruce D. Lawrey
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Publication number: 20210179903Abstract: Provided are adhesives comprising: (A) an aliphatic polyisocyanate; and (B) an aspartate-terminated prepolymer which is a reaction product of (B1) an aliphatic NCO-terminated prepolymer having a NCO content of from 0.5% to 35%, and (B2) a compound according to formula (I) wherein, X represents a linear or branched aliphatic group obtained by removing amino groups from a linear or branched aliphatic polyamine, R1 and R2 are identical or different and represent organic groups which are inert towards isocyanate groups at a temperature of 100° C. or less, R3 and R4 are identical or different and represent hydrogen or organic groups which are inert towards isocyanate groups at a temperature of 100° C. or less, n represents an integer with a value of at least 2, wherein the aspartate-terminated prepolymer (B) has a ratio of equivalents of NH groups to equivalents of NCO groups of 1.Type: ApplicationFiled: June 11, 2020Publication date: June 17, 2021Inventors: Raymond Zeliznik, Karl W. Haider, Francis C. Rossitto, Philip Jones, Matthew Stewart
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Publication number: 20210040362Abstract: Provided is an adhesive comprising a reaction product of (A) an aliphatic polyisocyanate having a molecular weight of from 132 to 700; and (B) a polyaspartate comprising a reaction product of (B1) a polyamine having a molecular weight of at least 240, and (B2) a Michael addition receptor, wherein viscosity @23° C. according to ASTM D1084-16, remains below 150 cps after four hours, and wherein the adhesive develops an acceptable bond strength to a substrate, defined as having a minimum of 150 g/in. measured @23° C. according to ASTM D 1876-01 or substrate tear, in less than five days after the substrate is laminated with the adhesive. The inventive flexible packaging adhesives are free of aromatic amines and may find use in multilayer laminates for a variety of industries, including the food processing, cosmetics, and detergents industries.Type: ApplicationFiled: August 7, 2020Publication date: February 11, 2021Inventors: Karl W. Haider, Raymond Zeliznik, Philip Jones
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Publication number: 20210039359Abstract: Provided is an adhesive comprising a reaction product of (A1) an aliphatic isocyanate having an NCO group content of 18 to 64 and (A2) a polyol or polyamine having a molecular weight of from 400 to 4000; and (B) a polyaspartate compound, wherein viscosity of the adhesive, as measured @ 23° C. according to ASTM D4212-16, remains below 60 seconds for after four hours, and wherein the adhesive develops an acceptable bond strength to a substrate, defined as having a minimum of 150 g/in. measured @ 23° C. according to ASTM D 1876-01 or substrate tear, in less than or equal to five days after the substrate is laminated with the adhesive. The adhesives are free of aromatic amines and may find use in multi-layered laminated films for the production of flexible packaging useful in a variety of industries, including the food processing, cosmetics, and detergents industries.Type: ApplicationFiled: August 6, 2020Publication date: February 11, 2021Inventors: Karl W. Haider, Raymond Zeliznik, Philip Jones
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Publication number: 20190211131Abstract: In one or more embodiments, the present invention provides a novel approach to the addition of plasticizers for softening TPUs, i.e., lowering the durometer and the melt viscosity. This approach involves incorporating bonded sulfonate groups with quaternary ammonium counterions into the TPU. In one or more embodiments of the present invention, the softening of TPU is achieved by incorporating an ionic diol, such as N,N-bis (2-hydroxyethyl)-2-aminoethane-sulfonic acid (BES), coupled with various bulky alkyl ammonium cations, during the chain extension step of the TPU synthesis. It is believed that that steric hindrance of the bulky quaternary ammonium groups weakens the dipole-dipole interactions of the sulfonate groups and/or lowers the crystallinity of the hard block, thereby creating additional free volume that softens the polymer and lowers the melt viscosity.Type: ApplicationFiled: February 6, 2019Publication date: July 11, 2019Inventors: Matthew Becker, Robert A. Weiss, Zachary Kurtiss Zander, Don S. Wardius, Karl W. Haider, Bruce D. Lawrey
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Publication number: 20190185609Abstract: In one or more embodiments, the present invention provides a novel approach to the addition of plasticizers for softening TPUs, i.e., lowering the durometer and the melt viscosity. This approach involves incorporating bonded sulfonate groups with quaternary ammonium counterions into the TPU. In one or more embodiments of the present invention, the softening of TPU is achieved by incorporating an ionic diol, such as N,N-bis (2-hydroxyethyl)-2-aminoethane-sulfonic acid (BES), coupled with various bulky alkyl ammonium cations, during the chain extension step of the TPU synthesis. It is believed that that steric hindrance of the bulky quaternary ammonium groups weakens the dipole-dipole interactions of the sulfonate groups and/or lowers the crystallinity of the hard block, thereby creating additional free volume that softens the polymer and lowers the melt viscosity.Type: ApplicationFiled: February 26, 2019Publication date: June 20, 2019Inventors: Matthew BECKER, Robert A. WEISS, Zachary Kurtiss ZANDER, Don S. WARDIUS, Karl W. HAIDER, Bruce D. LAWREY
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Patent number: 10227440Abstract: In one or more embodiments, the present invention provides a novel approach to the addition of plasticizers for softening TPUs, i.e., lowering the durometer and the melt viscosity. This approach involves incorporating bonded sulfonate groups with quaternary ammonium counterions into the TPU. In one or more embodiments of the present invention, the softening of TPU is achieved by incorporating an ionic diol, such as N,N-bis (2-hydoxyethyl)-2-aminoethane-sulfonic acid (BES), coupled with various bulky alkyl ammonium cations, during the chain extension step of the TPU synthesis. It is believed that that steric hindrance of the bulky quaternary ammonium groups weakens the dipole-dipole interactions of the sulfonate groups and/or lowers the crystallinity of the hard block, thereby creating additional free volume that softens the polymer and lowers the melt viscosity.Type: GrantFiled: May 27, 2016Date of Patent: March 12, 2019Assignees: The University of Akron, Covestro, LLCInventors: Matthew Becker, Robert A. Weiss, Zachary Kurtiss Zander, Don S. Wardius, Karl W. Haider, Bruce D. Lawrey
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Patent number: 9994666Abstract: This invention relates to polyurethane/polyureas. These polyurethane/polyurea materials comprise the reaction product of (A) a polyisocyanate prepolymer having an NCO group content of about 4 to about 30% and an average functionality of 1.8 to 6, and (B) an isocyanate-reactive component comprising at least one aromatic diamine compound. The (A) polyisocyanate prepolymers herein comprise the reaction product of (1) at least one (cyclo)aliphatic polyisocyanate with (2) an organic compound having 1.8 to 5 hydroxyl groups and a hydroxyl equivalent weight of 150 to 2000 g/eq., and which is selected from the group consisting of OH-functional polybutadienes, OH-functional polyalkylene, OH-functional polyalkylene phthalates, OH-functional polyalkylene isophthalates, OH-functional polyalkylene terephthalates and mixtures thereof.Type: GrantFiled: December 17, 2013Date of Patent: June 12, 2018Assignee: COVESTRO LLCInventors: Karl W. Haider, Wendy Gustavich, Richard R. Roesler, Rick V. Starcher
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Publication number: 20160347900Abstract: In one or more embodiments, the present invention provides a novel approach to the addition of plasticizers for softening TPUs, i.e., lowering the durometer and the melt viscosity. This approach involves incorporating bonded sulfonate groups with quaternary ammonium counterions into the TPU. In one or more embodiments of the present invention, the softening of TPU is achieved by incorporating an ionic diol, such as N,N-bis (2-hydoxyethyl)-2-aminoethane-sulfonic acid (BES), coupled with various bulky alkyl ammonium cations, during the chain extension step of the TPU synthesis. It is believed that that steric hindrance of the bulky quaternary ammonium groups weakens the dipole-dipole interactions of the sulfonate groups and/or lowers the crystallinity of the hard block, thereby creating additional free volume that softens the polymer and lowers the melt viscosity.Type: ApplicationFiled: May 27, 2016Publication date: December 1, 2016Inventors: Matthew BECKER, Robert A. Weiss, Zachary Kurtiss Zander, Don S. Wardius, Karl W. Haider, Bruce D. Lawrey
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Patent number: 9133297Abstract: Provided are ultraviolet (UV)-curable polyols and polyurethane compositions made by reacting the inventive polyol with an isocyanate. The inventive ultraviolet (UV)-curable polyol is made by co-polymerizing an alkylene oxide, an unsaturated carboxylic acid or anhydride and a hydroxy functional compound in the presence of a double metal cyanide (DMC) complex catalyst such that the polyol has an ultra-low level of unsaturation. The inventive polyols may be used to produce prepolymers, which in turn may be useful in making thin films which in turn may provide such items as medical examination gloves and scientific gloves. The inventive ultraviolet (UV)-curable polyurethane compositions may also find use in or as coatings, adhesives, sealants, elastomers and the like.Type: GrantFiled: May 15, 2006Date of Patent: September 15, 2015Assignee: ALLNEX IP S.à.r.L.Inventors: Bi Le-Khac, Karl W. Haider, Ramesh Subramanian, Charles A. Gambino, James Edward Kassner, Hu Xiaowei, William J. Sim
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Publication number: 20150166712Abstract: This invention relates to polyurethane/polyureas. These polyurethane/polyurea materials comprise the reaction product of (A) a polyisocyanate prepolymer having an NCO group content of about 4 to about 30% and an average functionality of 1.8 to 6, and (B) an isocyanate-reactive component comprising at least one aromatic diamine compound. The (A) polyisocyanate prepolymers herein comprise the reaction product of (1) at least one (cyclo)aliphatic polyisocyanate with (2) an organic compound having 1.8 to 5 hydroxyl groups and a hydroxyl equivalent weight of 150 to 2000 g/eq., and which is selected from the group consisting of OH-functional polybutadienes, OH-functional polyalkylene, OH-functional polyalkylene phthalates, OH-functional polyalkylene isophthalates, OH-functional polyalkylene terephthalates and mixtures thereof.Type: ApplicationFiled: December 17, 2013Publication date: June 18, 2015Applicant: Bayer MaterialScience LLCInventors: KARL W. HAIDER, Wendy Gustavich, Richard R. Roesler, Rick V. Starcher
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Publication number: 20150166717Abstract: This invention relates to polyurethane/polyureas with improved catalysis and to a process for the preparation of these polyurethane/polyureas. These materials comprise the reaction product of (A) a (cyclo)aliphatic polyisocyanate or (cyclo)aliphatic polyisocyanate prepolymer, with (B) an isocyanate-reactive component comprising at least one aromatic diamine compound containing from 1 to 8 thiomethyl groups, in the presence of (C) one or more catalysts selected from the group consisting of tin (II) catalysts, bismuth (III) catalysts and mixtures thereof. Preferably, the materials are optically clear.Type: ApplicationFiled: December 17, 2013Publication date: June 18, 2015Inventors: Karl W. Haider, Julie Operchal, Richard R. Roesler, Rick Starcher, Stephanie Strazisar
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Publication number: 20140272375Abstract: This invention relates to coated polyurethane foams and to a process for preparing coated polyurethane foams. More specifically, these coated polyurethane foams comprise (a) a polyurethane foam substrate, and (b) at least one bilayer of a coating composition on the foam substrate which comprises (1) a layer of a positively or negatively charged carbon allotrope, and (2) a layer of a positively or negatively charged polymer. When the carbon allotrope is positively charged, the other material is negatively charged, and vice versa. The final product (i.e. coated polyurethane foam) contains at least 1% by weight of the coating composition, based on 100% by weight of the coated polyurethane foam. The foams described herein have a surface resistivity of less than or equal to 1012 ohms per square.Type: ApplicationFiled: July 8, 2013Publication date: September 18, 2014Inventors: Karl W. Haider, Stanley L. Hager, Jaime C. Grunlan, Yong Tae Park
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Publication number: 20130101540Abstract: The present disclosure is directed to aqueous dispersions comprising polyurethane and nanoparticles, and processes for preparing the aqueous dispersions. The dispersions comprise aqueous polyurethane dispersions having nanoparticles covalently incorporated into the polymer matrix. The dispersions are prepared by reacting isocyanate groups present on the polyurethane chain ends with free amine groups on a hydroxy- or amino-functionalized nanoparticle to covalently attach the polyurethane and the nanoparticle through urethane or urea linkages, respectively.Type: ApplicationFiled: October 21, 2011Publication date: April 25, 2013Applicant: Bayer MaterialScience LLCInventors: Serkan Unal, Yuliya Berezkin, Peter D. Schmitt, Karl W. Haider
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Publication number: 20130023599Abstract: The present invention provides polyurethane foams and elastomers made with an alkoxylated vegetable oil hydroxylate replacing at least a portion of the typically used petroleum-based polyol(s). Also provided are processes for making the inventive foams and elastomers and for making alkoxylated vegetable oil hydroxylates. The alkoxylated vegetable oil hydroxylates are environmentally-friendly, bio-based polyols which advantageously also offer the potential of improved hydrophobicity in polyurethane foams and elastomers. The inventive polyurethane foams and elastomers may find use in a wide variety of products such as automobile interior parts, polyurethane structural foams, floor coatings and athletic running tracks.Type: ApplicationFiled: September 26, 2012Publication date: January 24, 2013Applicant: Bayer MaterialScience LLCInventors: Yu-Ling Hsiao, Richard G. Skorpenske, Bryan D. Kaushiva, Kenneth G. McDaniel, Jose F. Pazos, Stanley L. Hager, Karl W. Haider
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Patent number: 8134022Abstract: The present invention relates to a polyether carbonate polyol made by copolymerizing a starter molecule with carbon dioxide, at a pressure ranging from about 10 psia to about 2,000 psia, and an alkylene oxide, at a temperature ranging from about 50° C. to about 190° C. and in the presence of from about 0.001 wt. % to about 0.2 wt. % of a substantially non-crystalline double metal cyanide (DMC) catalyst, wherein the polyol has an incorporated carbon dioxide content of from about 1 wt. % to about 40 wt. %, wherein the ratio of cyclic carbonate by-product to total carbonate is less than about 0.3 and wherein the weight percentages are based on the weight of the polyol. The inventive polyether carbonate polyols may find use in producing polyurethane foams, elastomers, coatings, sealants and adhesives with improved properties.Type: GrantFiled: September 13, 2010Date of Patent: March 13, 2012Assignee: Bayer MaterialScience LLCInventors: Karl W. Haider, Kenneth G. McDaniel, Sr., John E. Hayes, Jianzhong Shen