Compound Which Includes Phenolic Hydroxy Or Oxygen Containing Hetero Ring Reacted With A Lignin Or Lignin Containing Substance, Or Product Thereof Patents (Class 530/502)
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Patent number: 12203215Abstract: The present invention relates to a process for producing a lignin composition, which process comprises: providing a lignin slurry comprising water and a water miscible organic solvent; subjecting the lignin slurry to extraction at an extraction temperature of less than 100° C. for an extraction time of at least 1 minute to provide an extracted slurry; removing liquid from the extracted slurry to provide an extracted lignin; and suspending the extracted lignin in a polar organic solvent to provide a lignin composition having a dry matter content of at least 30% by weight. The present invention also relates to a lignin composition comprising hardwood Kraft lignin and a polar organic solvent, which composition has a dry matter content of at least 30% by weight. The present invention also relates to use of the lignin composition as a fuel.Type: GrantFiled: May 31, 2023Date of Patent: January 21, 2025Assignee: KØBENHAVNS UNIVERSITETInventor: Yohanna Cabrera Orozco
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Patent number: 12195491Abstract: The present invention relates to a process to manufacture lignin-based polyols (LBP) by ring opening polymerization (ROP) of oxiranes in the presence of lignin and in an organic solvent or mixture thereof using acidic catalysts. The LBP are suitable to manufacture polyurethanes, polycarbonates and polyesters.Type: GrantFiled: November 28, 2019Date of Patent: January 14, 2025Assignee: FUNDACION TECNALIA RESEARCH & INNOVATIONInventors: José Ramón Ochoa Gómez, Jonatan Pérez Arce, Belén Maestro Madurga, Eduardo José García Suárez
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Patent number: 12012514Abstract: This disclosure relates to extraction methods for compatibilizing lignocellulosic biomass and residues thereof with polymers to produce value-added composites therefrom and other value-added products generated during the extraction methods.Type: GrantFiled: December 5, 2023Date of Patent: June 18, 2024Assignee: PLANTOON TECHNOLOGIES KFT.Inventors: Krisztina Lévay, Noémi Petrovics, Soma Bedő, Tímea Borosné Stumphauser
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Patent number: 11802201Abstract: A curable green epoxy resin composition is described. More particularly, the curable green epoxy resin composition includes a biobinder isolated from bio-oil produced from animal waste, such as from swine manure. The biobinder can act as a curing agent for an epoxy resin component in the resin composition. Cured green epoxy resins, prepregs containing the curable green epoxy resin, and related composite materials are described. In addition, methods of preparing the curable green epoxy resin composition and of curing the curable green epoxy resin.Type: GrantFiled: November 8, 2021Date of Patent: October 31, 2023Assignee: North Carolina Agricultural and Technical State UniversityInventors: Lifeng Zhang, Elham H. Fini, Sidharth Reddy Karnati
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Patent number: 11691881Abstract: It is disclosed purifies industrial lignin, performs Mannich reaction on purified industrial lignin, aldehyde and amino acid, simultaneously dopes nitrogen and sulfur elements into lignin, and performs high-temperature activation to obtain the carbonized amino acid modified lignin in accordance with a principle of green chemistry; a porous carbon material is prepared from the carbonized amino acid modified lignin by means of a two-step activation method, and an electrochemical workstation is applied to investigate electrochemical performance of the carbonized amino acid modified lignin as a supercapacitor; layered porous carbon having high specific surface area is prepared, the layered porous carbon has high specific heat capacity and stable cycle performance without attenuation when the supercapacitor is prepared from the layered porous carbon, and the method used has a wide application prospect in the aspect of preparing a porous carbon material for the supercapacitor.Type: GrantFiled: November 11, 2022Date of Patent: July 4, 2023Assignee: JIANGNAN UNIVERSITYInventors: Ying Li, Gang Shi
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Patent number: 11650744Abstract: An electronic device may implement a virtual elastic queue in memory, where, as needed, the virtual elastic queue grows in size to accommodate more queue elements, or shrinks in size to free up queue-element capacity and space in the memory. The virtual elastic queue may include a virtual queue and one or more physical queues, where the virtual queue provides a mapping to the one or more physical queues, and where a data structure may represent queue elements in the one or more physical queues. Notably, the virtual queue may point to the one or more physical queues, and the one or more physical queues may point to physical queue memory where data elements are enqueued and dequeued. Note that the virtual elastic queue may not have a predefined memory size and, up to a size of the memory, may not be constrained.Type: GrantFiled: June 21, 2021Date of Patent: May 16, 2023Assignee: ARRIS Enterprises LLCInventor: Rakesh G. Hansalia
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Patent number: 11168207Abstract: A curable green epoxy resin composition is described. More particularly, the curable green epoxy resin composition includes a biobinder isolated from bio-oil produced from animal waste, such as from swine manure. The biobinder can act as a curing agent for an epoxy resin component in the resin composition. Cured green epoxy resins, prepregs containing the curable green epoxy resin, and related composite materials are described. In addition, methods of preparing the curable green epoxy resin composition and of curing the curable green epoxy resin.Type: GrantFiled: January 28, 2019Date of Patent: November 9, 2021Assignee: North Carolina Agricultural and Technical State UniversityInventors: Lifeng Zhang, Elham H. Fini, Sidharth Reddy Karnati
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Patent number: 10800891Abstract: A process for valorization of lignin includes the steps of mixing lignin; a MOF catalyst metalated with a metal atom selected from the group consisting of Fe, Mn, Co, Cu, or Ni, and combinations thereof; an oxidizing agent; and an aqueous solvent. The product of this process, a charged polyacid-containing species derived from lignin, may be included in a dispersion with a dispersible particulate material, and an aqueous dispersing medium.Type: GrantFiled: March 7, 2017Date of Patent: October 13, 2020Assignee: National Technology & Engineering Solutions of Sandia, LLCInventors: Michael S. Kent, Mark D. Allendorf, Vitalie Stavila
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Patent number: 10676688Abstract: The present invention relates to a composition comprising lignin and a solvent where the lignin is functionalized with an ether group.Type: GrantFiled: June 15, 2016Date of Patent: June 9, 2020Assignee: REN FUEL K2B ABInventors: Christian Dahlstrand, Alexander Orebom, Joseph Samec, Supaporn Sawadjoon, Joakim Löfstedt
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Patent number: 10604615Abstract: A rigid polyurethane foam which is a polymerization product of a composition including a concentrated acid hydrolytic lignin, a polyol, and an isocyanate, and a method of preparing the rigid polyurethane foam.Type: GrantFiled: November 5, 2015Date of Patent: March 31, 2020Assignee: CJ CHEILJEDANG CORPORATIONInventors: Sun Joo Moon, Da Eun Kim, Jeung Yil Park, Sang Mok Lee, Min Ho Jung, Young Ran Kim, Jung Min Kim, Jin Hwa Chang
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Patent number: 10239904Abstract: Lignin-rich starting material is suspended in a first medium, which is acidic and aqueous, to form a aqueous acidic suspension, which is heated and allowed to form two continuous phases, a thermoplastic lignin phase and an aqueous phase. The thermoplastic lignin phase is separated from the aqueous phase and passed through a shape giving process into a second medium which is at a temperature lower than that of the thermoplastic lignin phase and in which the thermoplastic lignin phase is essentially insoluble. Solid lignin formed in the second medium is recovered.Type: GrantFiled: October 12, 2016Date of Patent: March 26, 2019Assignee: VALMET TECHNOLOGIES OYInventors: Eric Enqvist, Ville Tarvo, Panu Tikka, Tobias Wittmann, Henrik Wallmo, Anders Littorin
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Patent number: 9902815Abstract: In this study, commercially available softwood lignin was esterified with tall oil fatty acid (TOFA) and tested as barrier material in fiber-based packaging material. The modified lignin samples were applied with a bar coater forming an even coating on the paperboard substrate. A significant decrease in WVTR and OTR value was observed for paperboard coated with the modified lignin as well as pure TOFA used as a reference. In contrast to the TOFA coating, the modified lignin coatings exhibited a high and stable contact angle. The coating material did not affect the tensile strength of the paperboard. According to the results, the demonstration of the conversion of lignin into a value added product has been shown. Furthermore, the novel coating material shows promising properties for the development as sustainable barrier material in fiber-based packaging material to replace oil-placed barriers.Type: GrantFiled: October 8, 2012Date of Patent: February 27, 2018Assignee: Teknologian tutkimuskeskus VTT OyInventors: Tarja Tamminen, Jarmo Ropponen, Eva-Lena Hult, Kristiina Poppius-Levlin
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Patent number: 9487794Abstract: The invention relates to nucleic acids encoding a feruloyl-CoA:monolignol transferase and the feruloyl-CoA:monolignol transferase enzyme that enables incorporation of monolignol ferulates, for example, including p-coumaryl ferulate, coniferyl ferulate, and sinapyl ferulate, into the lignin of plants.Type: GrantFiled: July 22, 2011Date of Patent: November 8, 2016Assignees: Board of Trustees of Michigan State University, The University of British Columbia, Wisconsin Alumni Research FoundationInventors: Curtis Wilkerson, John Ralph, Saunia Withers, Shawn D. Mansfield
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Patent number: 9340623Abstract: Digestion of cellulosic biomass solids can be enhanced in the presence of a phenolic solvent. Methods for digesting cellulosic biomass solids can comprise providing cellulosic biomass solids in a digestion medium comprising a phenolic solvent; and heating the cellulosic biomass solids and the digestion medium in a digestion unit in the presence of molecular hydrogen and a slurry catalyst capable of activating molecular hydrogen, thereby forming an alcoholic component derived from the cellulosic biomass solids and liberating lignin from the cellulosic biomass solids into the digestion medium. The methods can further comprise converting at least a portion of the lignin into a phenolic solvent and returning the phenolic solvent formed from lignin to the cellulosic biomass solids.Type: GrantFiled: March 13, 2014Date of Patent: May 17, 2016Assignee: Shell Oil CompanyInventors: Joseph Broun Powell, Kimberly Ann Johnson
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Patent number: 9051244Abstract: The invention provides for a process for the depolymerization of lignin in an inert atmosphere to result in substituted phenolic monomer compounds. The process is catalyzed by heterogeneous solid acid catalysts and is carried out in batch or continuous mode.Type: GrantFiled: May 9, 2012Date of Patent: June 9, 2015Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCHInventors: Paresh Laxmikant Dhepe, Deepa Ayillath Kutteri
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Patent number: 8993735Abstract: The invention relates to a method for producing a lignin-based substrate for soil improvement having a water-storing property, characterized by the following steps: providing lignin, oxidizing the lignin in either an aqueous alkaline suspension or a pH-neutral aqueous suspension, the pH-neutral aqueous suspension being converted into an alkaline substance after the lignin has been oxidized, cross-linking the lignin in an aqueous alkaline medium using multifunctional compounds, and neutralizing, drying, and comminuting the lignin.Type: GrantFiled: February 10, 2011Date of Patent: March 31, 2015Assignee: Technische Universität DresdenInventors: Lars Passauer, Falk Liebner, Klaus Fischer, Joachim Katzur
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Publication number: 20150038665Abstract: Processes for the production of polyols from sources such as dried distillers grains plus solubles (DDGS) make use of a two-stage reaction scheme. In the first stage, the proteinaceous starting material is reacted with an aminating agent, such as diethanolamine (DEOA), to generate amino-amides and amides. These products are then reacted with an alkoxylating agent, preferably a substituted or unsubstituted epoxide to yield polyols. These polyols may be further reacted with isocyanates to give low-cost rigid polyurethane foams. In alternate forms, lignin may be directly converted to polyols by reaction with an alkoxylating agent, optionally followed by reaction with an isocyanate to produce polyurethanes.Type: ApplicationFiled: October 16, 2014Publication date: February 5, 2015Inventors: Sukh Bassi, Michael Douglas Parker, Mihail Ionescu, Zoran Petrovic
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Publication number: 20140378671Abstract: Modified lignin having covalently attached phosphorous containing groups and methods for preparing such compounds are described herein. The modified lignin described herein provides a renewable source of flame retardant material.Type: ApplicationFiled: September 8, 2014Publication date: December 25, 2014Inventor: Glen Leon BRIZIUS
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Patent number: 8822657Abstract: In one aspect, a process for treating woody plant material is provided, the process involving contacting the plant material with a continuous flow of an aqueous ethanol solution at elevated temperature and pressure under conditions that promote extraction of ethanol-soluble lignin from the plant material and retention of hemicellulose sugars, xylose and cellulose in the treated plant material solids. In another aspect, a process for extracting hemicellulose sugars from lignin-depleted plant material solids is provided, the process involving contacting lignin-depleted plant material with water at elevated temperature and pressure under conditions that promote extraction of hemicellulose sugars from the plant material; and recovering hemicellulose sugars from the liquid mixture.Type: GrantFiled: September 12, 2012Date of Patent: September 2, 2014Assignee: Vertichem CorporationInventors: Helene Belanger, Ross L. Prestidge, Tony James Lough, James D. Watson, Jia-Long Yao, Clare Elton, Alan MacFarlane, Mohammed Mehdi Farid, John Chen
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Publication number: 20140235132Abstract: Modified lignin having covalently attached phosphorous containing groups and methods for preparing such compounds are described herein. The modified lignin described herein provides a renewable source of flame retardant material.Type: ApplicationFiled: April 24, 2014Publication date: August 21, 2014Applicant: EMPIRE TECHNOLOGY DEVELOPMENT LLCInventor: Glen Leon BRIZIUS
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Publication number: 20140200324Abstract: Processes for the production of polyols from sources such as dried distillers grains plus solubles (DDGS) make use of a two-stage reaction scheme. In the first stage, the proteinaceous starting material is reacted with an aminating agent, such as diethanolamine (DEOA), to generate amino-amides and amides. These products are then reacted with an alkoxylating agent, preferably a substituted or unsubstituted epoxide to yield polyols. These polyols may be further reacted with isocyanates to give low-cost rigid polyurethane foams. In alternate forms, lignin may be directly converted to polyols by reaction with an alkoxylating agent, optionally followed by reaction with an isocyanate to produce polyurethanes.Type: ApplicationFiled: February 1, 2013Publication date: July 17, 2014Applicants: PITTSBURG STATE UNIVERSITY, MGPI PROCESSING, INC.Inventors: Sukh Bassi, Michael Douglas Parker, Mihail Ionescu, Zoran Petrovic
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Publication number: 20140194603Abstract: The invention relates to a method for the production of a precursor for the production of carbon- and activated carbon fibres according to the wet- or air-gap spinning method, in which a solution of lignin and a fibre-forming polymer in a suitable solvent is extruded through the holes of a spinning nozzle into a coagulation bath, the formed thread is stretched and subsequently treated, dried at an elevated temperature and then wound up. The lignin-containing thread is an economical starting material for the production of carbon- and activated carbon fibres.Type: ApplicationFiled: May 16, 2012Publication date: July 10, 2014Applicant: STORA ENSO OYJInventors: Andre Lehmann, Horst Ebeling, Hans-Peter Fink
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Publication number: 20140121360Abstract: One example embodiment includes inserting a chemical reagent into a process stream that contains one or more lignins to form one or more modified lignins. The formed one or more modified lignins are different than the one or more lignins in the process stream. The one or more modified lignins can be formed in the process stream before a precipitation stage and then separated from the process stream. Also, contaminates can be removed from the separated one or more modified lignins and the one or more modified lignins can be pressed and dried.Type: ApplicationFiled: October 29, 2013Publication date: May 1, 2014Applicant: Cyclewood Solutions, Inc.Inventors: Nhiem Cao, Kevin Oden
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Publication number: 20140039168Abstract: A lignosulfonate compound for phase change ink of the formula wherein R is hydrogen or and wherein the cationic counterion+ is a nitrogen-alkyl cationic counterion, a nitrogen-aryl cationic counterion, a nitrogen-alkylaryl cationic counterion, or a nitrogen arylalkyl cationic counterion; and wherein the cationic counterion contains at least eight carbon atoms.Type: ApplicationFiled: August 3, 2012Publication date: February 6, 2014Applicant: Xerox CorporationInventors: Mihaela Maria Birau, C. Geoffrey Allen, Salma Falah Toosi, Biby Esther Abraham, Peter G. Odell
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Publication number: 20140039144Abstract: Compositions comprising lignin and low levels of undesirable impurities, such as compounds containing sulfur, nitrogen, or metals, are disclosed.Type: ApplicationFiled: October 8, 2013Publication date: February 6, 2014Applicant: Renmatix, Inc.Inventors: Michel Adam Simard, Srinivas Kilambi, Kiran L. Kadam
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Patent number: 8617480Abstract: A concentrated acid treatment unit is composed of a reaction section and an agitation extraction section. A phenol sorped raw material obtained by defatting botanical resource-derived raw material by solvent to subject sorption phenols to sorption is introduced, thus obtaining mixed solution of phenol solution including a lignophenol derivative and concentrated acid solution including a cellulose hydrolysate. The reaction section agitates and mixes the phenol sorped raw material and concentrated acid to cause cellulose to be swollen to thereby convert lignin to lignophenol. A part of the cellulose is subjected to hydrolysis. The agitation extraction section receives the treated liquid sent from the reaction section and adds phenols for extraction thereto to cause lignophenol dispersed in the concentrated acid solution to be dissolved and extracted in phenols for extraction.Type: GrantFiled: October 21, 2009Date of Patent: December 31, 2013Assignees: Japan Science and Technology Agency, Kansai Chemical Engineering Co., Ltd.Inventors: Masamitsu Funaoka, Keigo Mikame, Hideo Noda
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Publication number: 20130331555Abstract: Technology for separating lignin from alkaline solutions which arise in production of cellulose is presented. Isolated lignin can be applied, for instance, for production of carbon fibre, adhesives and binding materials, antioxidants and organic chemicals. Starting materials are non-woody plant materials, from which lignin is dissolved by sulphur free alkaline solutions at temperatures below 130° C. Lignin is precipitated by acid, and purified by hydrolyzing hemicellulose by acid or by enzymatic reactions or a combination of these. Lignin separated has a closely similar structure as lignin in plant material, and its content of functional atom groups can be controlled by changes in processing conditions.Type: ApplicationFiled: March 6, 2012Publication date: December 12, 2013Inventors: Yrjö Mälkki, Jussi Sipilä
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Publication number: 20130303711Abstract: A method for producing a trans-esterified hydroxypropyl lignin (HPL) is provided in one example embodiment and includes precipitating a lignin, dissolving the precipitated lignin in a solution, adding a reagent to the solution, adjusting the pH of the solution, allowing reactions in the solution to occur for a predetermined amount of time, precipitating the solution to produce a precipitate, and washing, filtering, and drying the precipitate to produce the trans-esterified HPL.Type: ApplicationFiled: May 10, 2013Publication date: November 14, 2013Applicant: CYCLEWOOD SOLUTIONS, INC.Inventors: Nhiem Cao, Kevin Oden, Wolfgang G. Glasser
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Patent number: 8563633Abstract: A compound includes a lignophenol derivative having a weight average molecular weight in a range of 5000 to 10000, and satisfying the following formula (1): 3.0?pH value?4.5??(1) wherein the pH value is a determined value for a liquid mixture containing 0.2 g of the lignophenol derivative added to 40 ml of pure water.Type: GrantFiled: July 31, 2012Date of Patent: October 22, 2013Assignee: Fuji Xerox, Co., Ltd.Inventors: Manabu Kawashima, Kenji Yao
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Publication number: 20130237695Abstract: Methods for converting waste streams from the wood pulping industry to high-value surfactants are described. For example, isolated lignin and lignosulfonate or waste streams containing lignin and lignosulfonate can be directly converted to surfactants, or they can be first converted to methylol derivatives and treated with further reagents to produce surfactants.Type: ApplicationFiled: March 7, 2012Publication date: September 12, 2013Applicant: EMPIRE TECHNOLOGY DEVELOPMENT LLCInventor: Georgius Abidal Adam
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Publication number: 20130203901Abstract: A compound includes a lignophenol derivative having a weight average molecular weight in a range of 5000 to 10000, and satisfying the following formula (1): 3.0?pH value?4.5??(1) wherein the pH value is a determined value for a liquid mixture containing 0.2 g of the lignophenol derivative added to 40 ml of pure water.Type: ApplicationFiled: July 31, 2012Publication date: August 8, 2013Applicant: FUJI XEROX CO., LTD.Inventors: Manabu KAWASHIMA, Kenji YAO
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Publication number: 20120322990Abstract: The invention relates to a method for producing a lignin-based substrate for soil improvement having a water-storing property, characterized by the following steps: providing lignin, oxidizing the lignin in either an aqueous alkaline suspension or a pH-neutral aqueous suspension, the pH-neutral aqueous suspension being converted into an alkaline substance after the lignin has been oxidized, cross-linking the lignin in an aqueous alkaline medium using multifunctional compounds, and neutralizing, drying, and comminuting the lignin.Type: ApplicationFiled: February 10, 2011Publication date: December 20, 2012Applicant: TECHNISCHE UNIVERSITAET DRESDENInventors: Lars Passauer, Falk Liebner, Klaus Fischer, Joachim Katzur
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Publication number: 20120041183Abstract: A molecule possessing a primary or secondary amino group and an additional functionality capable of providing a novel or improved property to a cellulose material has been permanently attached to the cellulose material in aqueous media using a water-soluble carbodiimide as the coupling agent/activator. One such molecule is 5-aminofluorescein (abbreviated as “A-fluo”) and one such cellulose material is a papermaking pulp. Papers made from a pulp furnish containing, for example, 0.01 wt. % of the “A-fluo”-attached pulp show an embedded marker feature authenticable upon UV or visible light excitation. The “A-fluo”-attached pulp can also be used for the marking and identification of a pulp furnish.Type: ApplicationFiled: March 17, 2010Publication date: February 16, 2012Inventors: Thomas Q. Hu, Ali Hayek
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Publication number: 20120012035Abstract: A method for producing chemically modified lignin decomposition products. To this end, a lignin-containing starting material is decomposed into low-molecular and high-molecular lignin decomposition products under acid conditions in the presence of a liquid medium, and the low-molecular lignin decomposition products are at least largely separated in order to obtain a high-molecular fraction. Subsequently, the high-molecular lignin decomposition products present in the high-molecular fraction are converted into chemically modified lignin decomposition products. The chemically modified lignin decomposition products obtained in this way can be used, for example, as dispersing agents, complexing agents, phenol component, flocculant, thickener or auxiliary agents for cementous systems, coatings, paints or adhesives.Type: ApplicationFiled: March 19, 2010Publication date: January 19, 2012Applicant: SIKA TECHNOLOGY AGInventors: Norman Blank, Irene Schober, Philipp Rudolf Von Rohr, Tobias Voitl
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Publication number: 20110282038Abstract: In one aspect, a process for treating woody plant material is provided, the process involving contacting the plant material with a continuous flow of an aqueous ethanol solution at elevated temperature and pressure under conditions that promote extraction of ethanol-soluble lignin from the plant material and retention of hemicellulose sugars, xylose and cellulose in the treated plant material solids. In another aspect, a process for extracting hemicellulose sugars from lignin-depleted plant material solids is provided, the process involving contacting lignin-depleted plant material with water at elevated temperature and pressure under conditions that promote extraction of hemicellulose sugars from the plant material; and recovering hemicellulose sugars from the liquid mixture.Type: ApplicationFiled: July 22, 2011Publication date: November 17, 2011Applicant: BIOJOULE LIMITEDInventors: Helene BELANGER, Ross L. PRESTIDGE, Tony James LOUGH, James D. WATSON, Jia-Long Yao, Clare ELTON, Alan McFarlane, Mohammed Mehdi Farid, John Chen
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Patent number: 8012356Abstract: An object of the present invention is to provide a technique for separation/collection of a lignin derivative which is useful for the separation of a lignin derivative having a 1,1-diphenylpropane unit and/or a unit derived from the 1,1-diphenylpropane unit from a mixture system containing the lignin derivative. In the Present invention, a lignin derivative having a 1,1-diphenylpropane unit and/or a unit derived from the 1,1-dipheylpropane unit is allowed to contact with a metal oxide in a liquid medium, thereby separating the lignin derivative in the form retained on the metal oxide.Type: GrantFiled: June 6, 2006Date of Patent: September 6, 2011Assignee: Japan Science and Technology AgencyInventors: Masamitsu Funaoka, Mitsuru Aoyagi
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Publication number: 20110213057Abstract: A cationic electrodepositable coating composition is disclosed.Type: ApplicationFiled: February 26, 2010Publication date: September 1, 2011Inventors: David Fenn, Mark P. Bowman, Steven R. Zawacky, Ellor J. Van Buskirk, Peter Kamarchik
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Publication number: 20110196136Abstract: Provided is a Phase-Separation system plant for botanical resource, a conversion method, a concentrated acid treatment unit, and a concentrated acid treatment method by which lignin derivatives and hydrolyzed carbohydrate are manufactured out of a botanical resource efficiently and continuously. A concentrated acid treatment unit (3) is composed of a reaction section (20) and an agitation extraction section (25). A phenol sorped raw material (16) obtained by defatting botanical resource-derived raw material (15) by solvent (14) to subject sorption phenols (13) to sorption is introduced, thus obtaining mixed solution of phenol solution including a lignophenol derivative and concentrated acid solution including a cellulose hydrolysate. The reaction section (20) agitates and mixes the phenol sorped raw material (16) and concentrated acid (21A) to cause cellulose to be swollen to thereby convert lignin to lignophenol. A part of the cellulose is subjected to hydrolysis.Type: ApplicationFiled: October 21, 2009Publication date: August 11, 2011Applicants: JAPAN SCIENCE AND TECHNOLOGY AGENCY, KANSAI CHEMICAL ENGINEERING CO., LTD.Inventors: Masamitsu Funaoka, Keigo Mikame, Hideo Noda
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Patent number: 7985847Abstract: In one aspect, a process for treating woody plant material is provided, the process involving contacting the plant material with a continuous flow of an aqueous ethanol solution at elevated temperature and pressure under conditions that promote extraction of ethanol-soluble lignin from the plant material and retention of hemicellulose sugars, xylose and cellulose in the treated plant material solids. In another aspect, a process for extracting hemicellulose sugars from lignin-depleted plant material solids is provided, the process involving contacting lignin-depleted plant material with water at elevated temperature and pressure under conditions that promote extraction of hemicellulose sugars from the plant material; and recovering hemicellulose sugars from the liquid mixture.Type: GrantFiled: December 15, 2009Date of Patent: July 26, 2011Assignee: BioJoule Ltd.Inventors: Helene Belanger, Ross L. Prestidge, Tony James Lough, James D. Watson, Clare Elton
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Patent number: 7922912Abstract: An object of the present invention is to provide a technique for separation/collection of a lignin derivative which is useful for the separation of a lignin derivative having a 1,1-diphenylpropane unit and/or a unit derived from the 1,1-diphenylpropane unit from a mixture system containing the lignin derivative. In the Present invention, a lignin derivative having a 1,1-diphenylpropane unit and/or a unit derived from the 1,1-dipheylpropane unit is allowed to contact with a metal oxide in a liquid medium, thereby separating the lignin derivative in the form retained on the metal oxide.Type: GrantFiled: June 6, 2006Date of Patent: April 12, 2011Assignee: Japan Science and Technology AgencyInventors: Masamitsu Funaoka, Mitsuru Aoyagi
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Publication number: 20100326880Abstract: This invention relates to a hydrocarbon conversion process additive and related processes, such as upgrading a heavy hydrocarbon material and making sponge coke. The hydrocarbon conversion process additive works with thermal processes, catalytic processes, or thermal-catalytic processes. The hydrocarbon process conversion additive includes lignin or macromolecular substructures of lignin like para-coumaryl alcohol, coniferyl alcohol, or sinapyl alcohol.Type: ApplicationFiled: June 25, 2009Publication date: December 30, 2010Applicant: BP CORPORATION NORTH AMERICA INC.Inventors: Sudhakar Chakka, Bang Xu
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Publication number: 20100204368Abstract: The invention relates to functionalized lignin, rubber compositions which contain functionalized lignin and to products which have at least one component comprised of such rubber composition.Type: ApplicationFiled: January 8, 2010Publication date: August 12, 2010Inventors: David Andrew Benko, Bruce Raymond Hahn, Martin Paul Cohen, Shawn Matthew Dirk, Kirsten Nicole Cicotte
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Publication number: 20100075878Abstract: Novel modified lignin polymers containing anionic, cationic, and/or alkoxy substitution are disclosed. Further, new cleaning compositions including the novel substituted lignin polymers are disclosed. Methods of forming the modified lignin polymers and cleaning compositions are disclosed.Type: ApplicationFiled: September 18, 2009Publication date: March 25, 2010Applicant: The Procter & Gamble CompanyInventors: Yonas Gizaw, Bruno Albert Jean Hubesch, Jeffrey Scott Dupont, Xiaoru Jenny Wang, Luke Andrew Zannoni
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Patent number: 7649086Abstract: An integrated process for the production of ethanol from woody plant material is provided, the process comprising: contacting a continuous flow of the plant material with a counter-current continuous flow of an aqueous ethanol solution at elevated temperature and pressure to provide plant material depleted of lignin; removing ethanol from the lignin-depleted plant material; contacting a continuous flow of the lignin-depleted plant material with water at elevated temperature and pressure to solubilize xylose within the plant material; and hydrolyzing cellulose present in the plant material to form glucose, which in turn is fermented to produce ethanol.Type: GrantFiled: May 8, 2007Date of Patent: January 19, 2010Assignee: Biojoule Ltd.Inventors: Helene Belanger, Ross L. Prestidge, Tony James Lough, James D. Watson, Jia-Long Yao
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Publication number: 20090209739Abstract: An object of the present invention is to provide a technique for separation/collection of a lignin derivative which is useful for the separation of a lignin derivative having a 1,1-diphenylpropane unit and/or a unit derived from the 1,1-diphenylpropane unit from a mixture system containing the lignin derivative. In the Present invention, a lignin derivative having a 1,1-diphenylpropane unit and/or a unit derived from the 1,1-dipheylpropane unit is allowed to contact with a metal oxide in a liquid medium, thereby separating the lignin derivative in the form retained on the metal oxide.Type: ApplicationFiled: June 6, 2006Publication date: August 20, 2009Applicant: Japan Science and Technology AgencyInventors: Masamitsu Funaoka, Mitsuru Aoyagi
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Publication number: 20090062516Abstract: Lignin polymers having distinctive properties, including a generally high molecular weight and generally homogeneous size distribution, as well as preservation of native reactive side groups, are isolated by solvent extraction of plant materials. Methods for isolation of lignin polymers, and for use of the isolated lignin polymers are disclosed. Compositions containing lignin isolated from plant materials, such as carbon fiber composites, resins, adhesive binders and coatings, polyurethane-based foams, rubbers and elastomers, plastics, films, paints, nutritional supplements, food and beverage additives are disclosed. Xylose and xylose derivatives, furfural, fermentable sugars, cellulose and hemi-cellulose products may be used directly or further processed. The lignin polymers and other plant-derived products disclosed herein may be produced in abundance at low cost, and may be used as substitutes for feedstocks originating from fossil fuel or petrochemical sources in the manufacture of various products.Type: ApplicationFiled: September 2, 2008Publication date: March 5, 2009Applicant: BIOJOULE LIMITEDInventors: Helene BELANGER, Ross L. PRESTIDGE, Tony James LOUGH, James D. WATSON
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Patent number: 7498422Abstract: A lignophenol derivative is represented by Formula (1): wherein X1, X2 and X3 each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylene group, a hydroxyl group, a carboxyl group, an amino group, or an amide group; a and c each independently is an integer of 0 to 3; b is an integer of 0 to 4; and n is an integer of 1 to 10000.Type: GrantFiled: May 2, 2007Date of Patent: March 3, 2009Assignee: Fuji Xerox Co., Ltd.Inventor: Kenji Yao
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Publication number: 20080125544Abstract: A lignophenol derivative is represented by Formula (1): wherein X1, X2 and X3 each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylene group, a hydroxyl group, a carboxyl group, an amino group, or an amide group; a and c each independently is an integer of 0 to 3; b is an integer of 0 to 4; and n is an integer of 1 to 10000.Type: ApplicationFiled: May 2, 2007Publication date: May 29, 2008Applicant: FUJI XEROX CO., LTD.Inventor: Kenji Yao
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Patent number: 7323501Abstract: The present invention provides a process for producing novel lignin derivatives, which comprises using a lignophenol derivative containing a diphenylpropane unit formed by binding a carbon atom at an ortho-position relative to a phenolic hydroxyl group of a phenol derivative to a carbon atom at a benzyl-position of a phenylpropane fundamental unit of lignin, and binding an oxygen atom of the hydroxyl group and a ?-positional carbon atom under alkali conditions under which the hydroxyl group can dissociate, to obtain an arylcoumaran derivative containing an arylcoumaran unit in which a coumaran skeleton is bound to an aromatic ring of lignin.Type: GrantFiled: December 2, 2004Date of Patent: January 29, 2008Assignees: Kabushiki Kaisha MarutoInventor: Masamitsu Funaoka
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Patent number: 7276591Abstract: The present invention relates to biomass resin composition comprising a phenolized biomass substance and a reactive substance having a melting point of at most 100° C. other than phenol. The biomass resin composition is prepared by a process, which comprises adding a reactive substance such as a phenol derivative or drying oil into the reaction system, in the step of preparing a phenolized biomass substance by phenolizing a biomass substance with a phenol in the presence of an acid catalyst. The present invention provides a biomass resin composition, in which the melting point can be freely controlled and which is excellent in properties such as flowability, processability, water resistance and impact resistance and can be prepared by a simple process, and a process for preparing the same.Type: GrantFiled: March 24, 2004Date of Patent: October 2, 2007Assignee: Fuji Carbon Co., Ltd.Inventors: Yaoguang Yao, Chuji Kitagawa, Motonobu Fujimori, Kaoru Fujimori