Patents Assigned to Stepan Company
  • Patent number: 12129434
    Abstract: A hydraulic fracturing method is disclosed. A small proportion of a nonionic surfactant is used in combination with an acrylamide polymer emulsion friction reducer, the proppant, and the base water to boost the viscosity of the fracturing fluid. The nonionic surfactant has a calculated HLB within the range of 10 to 17. The nonionic surfactants include selected aralkylated phenol ethoxylates, amine or amidoamine ethoxylates, mixed EO/PO alcohol alkoxylates, ethoxylated alcohols, ethoxylated amides, and alkylphenol ethoxylates. The nonionic surfactant boosts the viscosity of the fracturing fluid, promotes proppant transfer, and enables more-efficient hydrocarbon production.
    Type: Grant
    Filed: June 24, 2021
    Date of Patent: October 29, 2024
    Assignee: STEPAN COMPANY
    Inventors: Alhad Phatak, Yonglin Ren, Brian Seymour-Loya, Aaron Sanders
  • Patent number: 12104008
    Abstract: Polyether- or polyester-epoxide polymer (PEEP) compositions are disclosed. The compositions comprise reaction products of a polyepoxide compound and a polyol composition. The polyol composition has a melting point within the range of 20° C. to 100° C. and a hydroxyl number less than 35 mg KOH/g. The PEEP composition is a solid-solid phase-change material. As measured by differential scanning calorimetry (DSC) at a heating/cooling rate of 10° C./minute, the PEEP composition has a transition temperature within the range of ?10° C. to 70° C., a latent heat at the transition temperature within the range of 30 to 200 J/g, and little or no detectable hysteresis or supercooling upon thermal cycling over at least five heating/cooling cycles that encompass the transition temperature.
    Type: Grant
    Filed: August 14, 2020
    Date of Patent: October 1, 2024
    Assignee: STEPAN COMPANY
    Inventors: Zhenhua Cui, Warren A. Kaplan, Sarah Wolek
  • Patent number: 12043857
    Abstract: Provided is a method for improving the yield of rhamnolipids comprising culturing in medium containing a triglyceride containing oil and sweetener as a carbon source.
    Type: Grant
    Filed: September 13, 2021
    Date of Patent: July 23, 2024
    Assignee: Stepan Company
    Inventor: Nattaporn Lohitharn
  • Patent number: 12037489
    Abstract: A rigid PU or PU-PIR foam comprising a reaction product of water, a catalyst, a foam-stabilizing surfactant, a polyisocyanate, a blowing agent and a blend comprising: (a) 90 to 99 wt. % of an aromatic polyester polyol having a hydroxyl number within the range of 150 to 400 mg KOH/g; and (b) 1 to 10 wt. % of a fatty acid derivative selected from the group consisting of C8 to C18 fatty acid esters and C8 to C18 fatty acid amides.
    Type: Grant
    Filed: May 8, 2023
    Date of Patent: July 16, 2024
    Assignee: STEPAN COMPANY
    Inventors: Warren A. Kaplan, Zhenhua Cui, Sarah Wolek
  • Patent number: 11993708
    Abstract: Blends comprising an aromatic polyester polyol and a 1 to 10 wt. % of a fatty acid derivative are disclosed. The fatty acid derivative is a C8 to C18 fatty acid ester or a C8 to C18 fatty acid amide. Also disclosed are rigid PU or PU-PIR foams that comprise a reaction product of water, a catalyst, a foam-stabilizing surfactant, a polyisocyanate, a blowing agent, and the polyester polyol/fatty acid derivative blends. Surprisingly, low-temperature R-values of rigid foams based on pentane blowing agents can be improved significantly by using blends of aromatic polyester polyols and a minor proportion of readily available fatty acid derivatives. In some aspects, the difference between initial R-values of the foam measured at 75° F. and 40° F. is at least 5% greater than that of a similar foam prepared in the absence of the fatty acid derivative.
    Type: Grant
    Filed: October 9, 2020
    Date of Patent: May 28, 2024
    Assignee: STEPAN COMPANY
    Inventors: Warren A. Kaplan, Zhenhua Cui, Sarah Wolek
  • Patent number: 11981879
    Abstract: Dilutable concentrates useful for hard surface cleaners with improved film/streak performance on high-energy surfaces are disclosed. The concentrates comprise a nonionic alkoxylated surfactant and a polyetheramine. A relatively minor proportion of a polyetheramine can resolve film/streak issues that characterize hard surface cleaners formulated with nonionic surfactants. The efficacy of polyetheramines for improving film/streak performance of hard surface cleaners formulated with nonionic alkoxylated surfactants far exceeds the benefits available from known improvements, such as the use of hydrotropes. Other inventive dilutable concentrates and hard surface cleaners comprise an amine-functional hydrophobe and an auxiliary surfactant. Still other dilutable concentrates or hard surface cleaners comprise a nonionic alkoxylated surfactant and lactic acid. An improved method for measuring film/streak properties of hard surface cleaners is also disclosed.
    Type: Grant
    Filed: January 18, 2021
    Date of Patent: May 14, 2024
    Assignee: STEPAN COMPANY
    Inventors: Ronald A. Masters, Mona Marie Knock, Patrick Shane Wolfe, Timothy A. Boebel, Xue Min Dong, Dennis S. Murphy
  • Patent number: 11970571
    Abstract: Noise, vibration, or harshness (NVH) properties of an industrial or consumer product are reduced by incorporating therein an effective amount of a polyether- or polyester-epoxide polymer (PEEP) composition. The PEEP compositions are one-component or two-component reaction products of a polyepoxide compound and a polyol composition. The PEEP compositions have a glass-transition temperature within the range of ?50° C. to 50° C. and a loss factor of at least 0.5 by ASTM D5992 over a temperature range of at least 15 Celsius degrees at one or more frequencies within the range of 0.1 to 10,000 Hz. The PEEP compositions provide NVH damping over a broad temperature range, have improved flexibility compared with conventional epoxy technologies, avoid amine and isocyanate reactants, and can be tailored to meet target specifications.
    Type: Grant
    Filed: October 26, 2021
    Date of Patent: April 30, 2024
    Assignee: STEPAN COMPANY
    Inventors: Michael E. O'Brien, Warren A. Kaplan, Sarah Wolek, Jennifer S. Westfall, Calvin Gang
  • Patent number: 11939434
    Abstract: Copolymers comprising recurring units of a phenyl glycidyl ether and alkylene oxides are disclosed. Some of the copolymers comprise a di- or polyfunctional nucleophilic initiator and recurring units of the phenyl glycidyl ether and an alkylene oxide. The di- or polyfunctional nucleophilic initiator is an alcohol, phenol, amine, thiol, thiophenol, sulfinic acid, or deprotonated species thereof. Other copolymers comprise a monofunctional nucleophilic initiator selected from thiols, thiophenols, aralkylated phenols, sulfinic acids, secondary amines, C10-C20 terpene alcohols, and deprotonated species thereof. Pigments dispersions comprising the copolymers are also disclosed. The copolymers meet the growing needs of the industry with their ease of manufacture, diverse structures, and desirable performance attributes for dispersing a wide range of organic and inorganic pigments. Agricultural applications for the copolymers are also disclosed.
    Type: Grant
    Filed: March 31, 2020
    Date of Patent: March 26, 2024
    Assignee: STEPAN COMPANY
    Inventors: Timothy A. Boebel, Xue Min Dong, E. Carolina Rojas, Renee Luka, Gary Luebke, Paul W. Knox
  • 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: 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
  • 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
  • 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