Patents Assigned to Stepan Company
  • Patent number: 11919993
    Abstract: Polyester polyols for use in low-VOC polyurethane compositions are disclosed. The polyester polyols are the reaction product of at least one aliphatic polycarboxylic acid, at least one alkoxylated polyalcohol having a functionality of 2.0 or greater, and one or more polyalcohols other than an alkoxylated polyalcohol. The polyester polyols can be formulated into polyurethane compositions to obtain a polyurethane having a low VOC content. The polyurethane composition is particularly suitable for polyurethane coating applications.
    Type: Grant
    Filed: July 22, 2020
    Date of Patent: March 5, 2024
    Assignee: Stepan Company
    Inventors: Michael E. O'Brien, Jeffrey R. Janos
  • Patent number: 11898096
    Abstract: A hydraulic fracturing method for recovering oil from a low-temperature subterranean oil formation is disclosed. Before, during, or after inducing hydraulic fracturing within the formation, a particulate, degradable polyester diverting agent is introduced into the formation in an amount effective to improve oil production from the formation. The diverting agent is allowed to degrade, and oil is recovered. The diverting agent has a melting point greater than the average temperature of the formation and is selected from: (i) ethylene glycol succinates; (ii) acid-terminated ethylene glycol succinates; (iii) acid-terminated polyglycolic acids; (iv) acid-terminated polylactic acids; (v) mixtures of any of (i) through (iv) with a half acid ester; and (vi) mixtures of polylactic acids or polyglycolic acids with a half acid ester.
    Type: Grant
    Filed: June 15, 2020
    Date of Patent: February 13, 2024
    Assignee: Stepan Company
    Inventors: Douglas Kip Hillshafer, Sarah Wolek
  • Patent number: 11879093
    Abstract: A method for inhibiting corrosion of pipelines and other metal surfaces, particularly those used in the oil-and-gas industry, is disclosed. The method comprises treating a brine-exposed metal surface with a film-forming composition. The composition comprises a quaternary surfactant, which is made by reacting a polyalkylene glycol (PAG), a haloalkanoic acid, and a tertiary fatty amine that optionally incorporates amide or ester functionality. The surfactant comprises a PAG monoester quat and a PAG diester diquat and may have other components. The quaternary surfactants provide good corrosion protection and can partition effectively from an oily phase into a brine phase in the absence of agitation. The surfactants are easy to synthesize economically and have structures that can be tailored to meet local HLB requirements.
    Type: Grant
    Filed: July 29, 2020
    Date of Patent: January 23, 2024
    Assignee: STEPAN COMPANY
    Inventors: Maxime Feche, Mathieu Pepin, Elodie Shaw, Laure Canal, José Santiago, Milan Bartos, Alla Crabtree
  • Patent number: 11827544
    Abstract: A method of degrading 1,4-dioxane in the wastewater produced during the manufacture of alkyl ether sulfates is disclosed. The method includes the steps of (a) mixing from 100 to 10,000 ppm, preferably 1,000 to 4,000 ppm of ozone with the wastewater; (b) introducing H2O2 into the wastewater in an amount of 0.01 to 10, preferably 0.1 to 0.5 molar equivalents of H2O2 to ozone, and (c) mixing the ozone, H2O2, and wastewater to generate hydroxyl radicals reactive with the 1,4-dioxane, without the addition of a metal catalyst. The hydroxyl radicals react with the 1,4-dioxane and degrade it into carbon dioxide, water and/or carbonate. The method is effective to reduce a concentration of 1,4-dioxane in the wastewater from a range of about 10 ppm to about 1000 ppm of dioxane down to less than 5 ppb of 1,4-dioxane after treatment. The method is also effective for removing hydrocarbon species that may be present in the wastewater.
    Type: Grant
    Filed: December 9, 2022
    Date of Patent: November 28, 2023
    Assignee: Stepan Company
    Inventors: Matthew V. Vollmer, Donald E. Oulman, Aaron Brown, Dennis Smith, Doug Gustafson, Terry Applebury
  • Patent number: 11827836
    Abstract: A demulsified composition comprising a clear oil phase comprising hydrocarbons, a clear brine phase comprising up to 5 wt. % of a diethanolamine-based C8-C18 alkanolamide demulsifying agent, and a water-wetted solid phase.
    Type: Grant
    Filed: September 21, 2022
    Date of Patent: November 28, 2023
    Assignee: STEPAN COMPANY
    Inventors: Yongling Ginger Ren, Aaron Sanders, Jonathan Mohandessi
  • Publication number: 20230303443
    Abstract: A surfactant composition is disclosed comprising a first alkyl sulfate surfactant, optionally a second alkyl sulfate surfactant, and optionally an alkyl ether sulfate. The first and second alkyl sulfate surfactants have Formula (1): and the alkyl ether sulfate has Formula (2): in which R1 and R2 are independently selected linear or branched alkyl or a combination thereof having from 6 to 14 carbon atoms, y has an average value from 0.1 to 5, and M1 and M2 are cations independently selected from sodium, calcium, ammonium, or a combination of two or all of these. Use of the composition as a foaming agent for gypsum slurries, and of the gypsum slurries for formation of gypsum boards, are disclosed.
    Type: Application
    Filed: May 19, 2023
    Publication date: September 28, 2023
    Applicants: STEPAN COMPANY, SAINT-GOBAIN PLACO
    Inventors: Brian K. MIROUS, Hamouda Jaffel
  • Patent number: 11760889
    Abstract: Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives. Microscopy studies indicate that the unsaturated sodium sulfates in particular have a lamellar phase that should enable formulation at high actives levels. Sulfate compositions comprising 40 to 60 wt. % of a monounsaturated fatty primary alcohol sulfate and 40 to 60 wt. % of a secondary hydroxyalkyl primary alcohol sulfate are also disclosed.
    Type: Grant
    Filed: July 15, 2020
    Date of Patent: September 19, 2023
    Assignee: Stepan Company
    Inventors: David R. Allen, Marcos Alonso, Mary Beddaoui, Randal J. Bernhardt, Aaron Brown, Scott Dillavou, Xue Min Dong, Wilma Gorman, John C. Hutchison, Gary Luebke, Renee Luka, Franz Luxem, Andrew D. Malec, Ronald A. Masters, Dennis S. Murphy, Nicholas Pendleton, Irma Ryklin, Patti Skelton, Brian Sook, Chris Spaulding, Krista Turpin, Gregory Wallace, Michael Wiester, Patrick Shane Wolfe
  • Patent number: 11725132
    Abstract: Compositions may include those of the formula: (I) wherein R1 is an alkyl chain having a carbon number in the range of greater than 40 to 200, R2 is a multiester, R3 is hydrogen, an ion, or an alkyl chain having a carbon number in the range of 1 to 200, m is an integer selected from 0 to 4, and n is an integer selected from the range of 0 to 4, wherein the sum of m and n is 1 or greater. Compositions may include a reaction product of a polyisobutylene-substituted succinic anhydride and a hydroxy-functional dendrimer, wherein the molar ratio of polyisobutylene-substituted succinic anhydride to hydroxy-functional dendrimer is within the range of 10:1 to 30:1.
    Type: Grant
    Filed: October 14, 2021
    Date of Patent: August 15, 2023
    Assignee: STEPAN COMPANY
    Inventors: Rachael Anne Cole, Pradyumna Avinash Deshpande, Chandrashekhar Yeshwant Khandekar, Tore Nordvik, Loic Regnault De La Mothe, Elodie Shaw, Laure Canal, Marine Dugand, José Santiago
  • Patent number: 11686575
    Abstract: Methods and systems for determining the integrity of a manufactured board are disclosed. An example system includes a testing platform configured to secure the manufactured board, a sensor configured to measure a parameter corresponding to a flatness of a surface of the board, and a controller. The controller is configured to identify regions on the surface corresponding to one of a peak or a valley based on the parameter, and calculate a score representing the integrity of the manufactured board based on the identified peaks and valleys. The controller adjusts a flow rate, a pressure, a temperature, and position of a deposited substance in a manufacturing process based on a comparison with a height of the peak and/or a depth of the valley to stored peak heights and/or valley depths. In some examples, a mechanical tester determines a compressive strength and a density of the board at the identified regions.
    Type: Grant
    Filed: May 17, 2021
    Date of Patent: June 27, 2023
    Assignee: Stepan Company
    Inventors: Thomas K. Johnson, David J. Norberg, Daniel Yocius
  • Patent number: 11667821
    Abstract: One-component (1K) adhesive compositions (“PEEP” compositions) and a process for making them are disclosed. A polyepoxide is reacted with a polyether polyol composition, a polyester polyol composition, or both in the presence of a heat-activated Lewis acid catalyst at a temperature within the range of 100° C. to 220° C. for a time effective to cure the adhesive. The compositions are storage-stable under ambient conditions. Compared with conventional epoxy compositions, the 1K PEEP compositions offer improved room temperature lap shear strength, better resilience, and higher elongation. The 1K PEEP systems deliver a desirable balance of physical and mechanical properties while avoiding polyisocyanates and polyamine crosslinkers.
    Type: Grant
    Filed: June 15, 2021
    Date of Patent: June 6, 2023
    Assignee: STEPAN COMPANY
    Inventors: Michael E. O'Brien, Warren A. Kaplan, Jennifer S. Westfall
  • Patent number: 11584872
    Abstract: A low-VOC, two-component polyurethane adhesive is provided. The polyurethane adhesive has an A-side that includes an isocyanate and a non-reactive plasticizer, and a B-side that includes an aliphatic polyester polyol, a non-polyester polyol, and a urethane catalyst. The A-side and the B-side are reacted at a volume ratio of 1:1 and formulated at an NCO/OH index within the range of 0.90 to 1.10. The polyurethane adhesive is solvent-free and is particularly suitable for adhering a polymeric membrane to a substrate.
    Type: Grant
    Filed: October 5, 2021
    Date of Patent: February 21, 2023
    Assignee: Stepan Company
    Inventors: Warren A. Kaplan, Sarah Wolek
  • Patent number: 11560530
    Abstract: Surfactant compositions comprising an alkoxylate, a sulfate, or ether sulfate of a C10-C12 monounsaturated alcohol are disclosed. The alkoxylate, sulfate, or ether sulfate may derive from undecylenic acid or undecylenic alcohol. Compared with their saturated analogs, the monounsaturated alkoxylates, sulfates, and ether sulfates are less irritating, making them valuable for personal care, laundry, cleaners, and other household applications. Microscopy studies show that the alkoxylates, sulfates, and ether sulfates have favorable phase behavior over a wide range of actives levels, expanding opportunities for products with greater compaction. When combined with cationic surfactants, the alkoxylates, sulfates, and ether sulfates exhibit synergy, and they have improved solubility compared with their saturated analogs. The surfactants find value for the personal care, laundry and cleaning, emulsion polymerization, agricultural products, oilfield applications, and specialty foams industries.
    Type: Grant
    Filed: April 4, 2019
    Date of Patent: January 24, 2023
    Assignee: Stepan Company
    Inventors: Randal J. Bernhardt, Wilma Gorman, Ronald Masters
  • Patent number: 11543810
    Abstract: Methods and systems for manufacturing a foam board system are disclosed. In some examples, a system includes an applicator to distribute one or more fluids onto a substrate. One or more sensors configured to measure one or more characteristics of the one or more fluids. A control circuitry is configured to compare the one or more measured characteristics to one or more threshold characteristics, and to adjust one or more operating parameters of the system in response to a characteristic of the one or more measured characteristics falling outside a threshold of the one or more threshold characteristics.
    Type: Grant
    Filed: December 3, 2021
    Date of Patent: January 3, 2023
    Assignee: Stepan Company
    Inventors: Daniel Yocius, David J. Norberg, Sean O'Cuanaigh
  • Patent number: 11472994
    Abstract: A method for demulsifying a recovered drilling fluid is disclosed. A recovered drilling fluid is first combined with dilution water and a diethanolamine-based C8-C18 alkanolamide demulsifying agent. The recovered drilling fluid comprises hydrocarbons, a brine having at least 25% total dissolved solids, an emulsifier, and undissolved oil-wetted solids. In a second step, the mixture is separated, or is allowed to separate, into three distinct phases, including a clear oil phase comprising the hydrocarbons, a clear brine phase, and a water-wetted solid phase. Compositions suitable for use as demulsifiers and demulsified compositions are also disclosed. The alkanolamide demulsifying agents enable rapid, clean separation of phases and efficient recovery of 80% or more of the oil phase from the recovered drilling fluid.
    Type: Grant
    Filed: December 23, 2020
    Date of Patent: October 18, 2022
    Assignee: STEPAN COMPANY
    Inventors: Yongling Ginger Ren, Aaron Sanders, Jonathan Mohandessi
  • Patent number: 11439145
    Abstract: Agricultural compositions that employ structured surfactant systems to suspend water-insoluble or sparingly soluble agricultural actives and/or adjuvants are disclosed. Also disclosed are agricultural compositions that combine structured surfactant systems with electrolytes to form structured electrolyte compositions. The structured surfactant systems, both with and without electrolyte, suspend one or more agricultural actives and/or crop oil and non-aqueous adjuvants to provide agricultural compositions that can combine combinations of actives in a single, stable composition.
    Type: Grant
    Filed: February 13, 2020
    Date of Patent: September 13, 2022
    Assignee: STEPAN COMPANY
    Inventors: Kelly Buchek, Eric M. Weber, Elodie Shaw, Krista L. Turpin, Andrea B. E. Brayton, Julien Guillan, Dave R. Allen
  • Patent number: 11274242
    Abstract: Compositions comprising an acrylamide polymer emulsion and a nonionic surfactant suitable for use as friction reducers for hydraulic fracturing are disclosed. The nonionic surfactants include aralkylated phenol ethoxylates, amine ethoxylates, amidoamine ethoxylates, linear or branched alcohol EO/PO alkoxylates, ethoxylated alcohols, alkylphenol ethoxylates, and EO-capped poly(oxypropylene) block copolymers. Improved hydraulic fracturing processes in which an acrylamide polymer emulsion is used as a friction reducer are also described. In these processes, the surfactant is included in the composition with the acrylamide polymer friction reducer, or it is introduced separately into the process. The performance of low-cost polyacrylamide friction reducers can be boosted with a small proportion of certain readily available nonionic surfactants.
    Type: Grant
    Filed: February 24, 2020
    Date of Patent: March 15, 2022
    Assignee: STEPAN COMPANY
    Inventors: Brian Seymour-Loya, Aaron Sanders, Dawn Friesen, Gregory P. Dado
  • Patent number: 11208522
    Abstract: Lactide-based random polyester polyols for use in polyurethane compositions are disclosed. The polyester polyols have an OH value in the range of greater than 400 mg KOH/g up to 1100 mg KOH/g and are the reaction product of at least one polycarboxylic acid, at least one lactide, and one or more polyalcohols. The polyester polyols can be formulated into the B-side of a two part polyurethane composition to obtain a polyurethane having improved hardness and solvent resistance and a low VOC content. The polyurethane composition is particularly suitable for polyurethane coating applications.
    Type: Grant
    Filed: January 6, 2020
    Date of Patent: December 28, 2021
    Assignee: Stepan Company
    Inventors: Michael Edward O'Brien, Jeffrey R. Janos, Scott Yin
  • Patent number: 11203811
    Abstract: A corrosion inhibitor active and method for reducing corrosion of a metal surface in contact with a corrosive environment is disclosed. The corrosion inhibitor active is an organic sulfonated compound that is derived from the sulfonation of one or more carboxylic acids, internal olefins, or alpha-olefins having a carbon chain length of 15 to 26 carbon atoms. The method of reducing corrosion includes contacting the metal surface with an effective amount of the corrosion inhibitor active. The corrosion inhibitor active is useful in high temperature corrosive environments, such as those found in oil and gas operations.
    Type: Grant
    Filed: March 3, 2020
    Date of Patent: December 21, 2021
    Assignee: Stepan Company
    Inventors: Alla Crabtree, Laura Lee Whitlock
  • Patent number: 11180588
    Abstract: Compositions may include those of the formula: (I) wherein R1 is an alkyl chain having a carbon number in the range of greater than 40 to 200, R2 is a multiester, R3 is hydrogen, an ion, or an alkyl chain having a carbon number in the range of 1 to 200, m is an integer selected from 0 to 4, and n is an integer selected from the range of 0 to 4, wherein the sum of m and n is 1 or greater. Compositions may include a reaction product of a polyisobutylene-substituted succinic anhydride and a hydroxy-functional dendrimer, wherein the molar ratio of polyisobutylene-substituted succinic anhydride to hydroxy-functional dendrimer is within the range of 10:1 to 30:1.
    Type: Grant
    Filed: December 30, 2016
    Date of Patent: November 23, 2021
    Assignee: Stepan Company
    Inventors: Rachael Anne Cole, Pradyumna Avinash Deshpande, Chandrashekhar Yeshwant Khandekar, Tore Nordvik, Loic Regnault De La Mothe, Elodie Shaw, Laure Canal, Marine Dugand, José Santiago
  • Patent number: 11168238
    Abstract: A low-VOC, two-component polyurethane adhesive is provided. The polyurethane adhesive has an A-side that includes an isocyanate and a non-reactive plasticizer, and a B-side that includes an aliphatic polyester polyol, a non-polyester polyol, and a urethane catalyst. The A-side and the B-side are reacted at a volume ratio of 1:1 and formulated at an NCO/OH index within the range of 0.90 to 1.10. The polyurethane adhesive is solvent-free and is particularly suitable for adhering a polymeric membrane to a substrate.
    Type: Grant
    Filed: September 23, 2019
    Date of Patent: November 9, 2021
    Assignee: Stepan Company
    Inventors: Warren A. Kaplan, Sarah Wolek