Carboxylic Acid Anhydride, Or A Compound Having Halogen Bonded Directly To Acyclic Carbon By Nonionic Bonding, Reacted With A Lignin Or Lignin Containing Substance, Or Product Thereof Patents (Class 530/504)
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Patent number: 10717873Abstract: The present invention relates to a liquid lignin mixture comprising 3-50 wt % methanol, 12-50 wt % lignin and 5-85 wt % aqueous alkali solution wherein the concentration of said aqueous alkali solution is 1 to 50 wt % of alkali in water, based on the weight of said alkali solution prior to mixing with the other components of the mixture. The liquid lignin mixture can be used to manufacture lignin-based phenolic resins, which are particularly useful in the manufacture of laminates.Type: GrantFiled: March 20, 2017Date of Patent: July 21, 2020Assignee: Stora Enso OYJInventors: Ashar Zafar, Dimitri Areskogh, Jesper Ekström
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Patent number: 10030147Abstract: The present invention relates to a composition comprising a carrier liquid and lignin or lignin derivatives solubilized in said carrier liquid; wherein at least one of the hydroxyl groups of the lignin or lignin derivatives have been substituted with ester groups forming esterified lignin or lignin derivatives. The composition may be used for preparing fuels or lubricants.Type: GrantFiled: December 16, 2014Date of Patent: July 24, 2018Assignee: Ren Fuel K2B ABInventors: Joseph Samec, Joakim Löfstedt, Christian Dahlstrand, Alexander Orebom, Supaporn Sawadjoon
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Patent number: 8987428Abstract: 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: GrantFiled: March 7, 2012Date of Patent: March 24, 2015Assignee: Empire Technology Development LLCInventor: Georgius Abidal Adam
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Publication number: 20150051384Abstract: Disclosed is acetylated wood comprising one or more end grain surfaces, wherein the wood is selected from the species Red Alder and European Alder. The acetylation of these wood species surprisingly result s in a lowering of the water absorption by immersion at an end-grain surface. Thus, acetylation can be used for the purpose of lowering the water absorption by immersion at an end-grain surface of wood selected from the group consisting of Red Alder and European Alder. The invention also pertains to wood having tangential surfaces, showing a surprising extent of aggregate rays. Further disclosed is a method of providing stable discoloured acetylated Red Alder [and European Alder], comprising a step of subjecting the acetylated wood to UV exposure.Type: ApplicationFiled: January 31, 2013Publication date: February 19, 2015Applicant: TITAN WOOD LIMITEDInventors: Jonathan Philip Alexander, Hendrikus Petrus Maria Bongers
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Publication number: 20140235838Abstract: Described is a method to oxidize lignin or lignin sub-units. The method includes oxidation of secondary benzylic alcohol in the lignin or lignin sub-unit to a corresponding ketone in the presence of unprotected primarily aliphatic alcohol in the lignin or lignin sub-unit. The optimal catalyst system consists of HNO3 in combination with another Brønsted acid, in the absence of a metal-containing catalyst, thereby yielding a selectively oxidized lignin or lignin sub-unit. The method may be carried out in the presence or absence of additional reagents including TEMPO and TEMPO derivatives.Type: ApplicationFiled: February 20, 2013Publication date: August 21, 2014Applicant: Wisconsin Alumni Research FoundationInventors: Shannon S. Stahl, Alireza Rahimi
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Publication number: 20130180927Abstract: A method for making lignin-amines is provided. The method comprises providing a lignin; then modifying the lignin with modifier to create a modified lignin; and then reacting the modified lignin with an amine to form a lignin-amine. Suitable modifiers comprise acrylates. A method for coagulating suspended materials in a water stream is also disclosed. The method comprises providing a water stream and contacting the suspended materials in the water stream with at least one lignin-amine.Type: ApplicationFiled: January 13, 2012Publication date: July 18, 2013Applicant: GENERAL ELECTRIC COMPANYInventors: Hongchen Dong, Wenqing Peng, Larry Neil Lewis
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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: 20110308810Abstract: The systems and methods described herein provide for modified lignins and other compositions that may be useful as surfactants. These compositions have particular utility for energy-related applications. In embodiments, they may be useful for enhanced oil recovery. In embodiments, they may be useful for extracting bitumen from oil sands. In embodiments, they may be useful for environmental remediation.Type: ApplicationFiled: December 15, 2010Publication date: December 22, 2011Inventors: Kristoffer K. Stokes, David Soane, Michael C. Berg, Kevin T. Petersen, William A. Mowers
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Publication number: 20100331531Abstract: Methods of making esterified lignocellulosic materials and resulting compositions and articles are disclosed.Type: ApplicationFiled: June 17, 2010Publication date: December 30, 2010Applicant: Eastman Chemical CompanyInventor: John Peter Mykytka
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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: 20100152428Abstract: The disclosure includes lignin mixed esters comprising first ester groups and second ester groups wherein the number of carbon atoms in the first ester group differs from the number of carbon atoms in the second ester group by 3 or more and processes of making the same. The unique thermal glass transition temperature properties of such lignin mixed esters are described.Type: ApplicationFiled: December 12, 2008Publication date: June 17, 2010Applicant: WEYERHAEUSER COMPANYInventors: Angela P. Gifford, John A. Westland, Amar N. Neogi, Karen D. Ragan
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Patent number: 7691982Abstract: The dispersant of the present invention comprises at least one component unit derived from kraft lignin and/or its salt and at least one component unit derived from at least one water-soluble monomer. The novel lignin derivative of the present invention comprises at least one component unit derived from kraft lignin and/or its salt, at least one polyoxyalkylene chain, and at least one anionic functional group.Type: GrantFiled: September 22, 2005Date of Patent: April 6, 2010Assignee: Nippon Shokubai Co., Ltd.Inventors: Takashi Tomita, Tsuyoshi Hirata
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Patent number: 6572859Abstract: The invention relates to a hypoallergenic immunogenic molecule derived from the Phl p 6 allergen, wherein the Phl p6 molecule has an N-terminal and/or C-terminal deletion which makes the molecule at least substantially lack IgE binding capacity. The invention also relates to a hypoallergenic immunogenic combination of molecules derived from the Phl p 6 allergen, comprising (i) a Phl p 6 molecule having an N-terminal deletion which makes the molecule at least substantially lack IgE binding capacity, and (ii) a Phl p 6 molecule having a C-terminal deletion which makes the molecule at least substantially lack IgE binding capacity, which two molecules together encompass the complete sequence of Phl p 6. The invention further relates to the use of the hypoallergenic immunogenic molecule or molecule mixture in hyposensitization and diagnosis.Type: GrantFiled: October 26, 2000Date of Patent: June 3, 2003Assignees: Pharmacia Diagnostics ABInventors: Rudolf Valenta, Susanne Vrtala, Sabine Stummfoll, Hans Grönlund, Monika Grote, Luca Vangelista, Annalisa Pastore, Wolfgang R. Sperr, Peter Valent, Dietrich Kraft
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Patent number: 6485841Abstract: The present invention is directed to bio-oil compositions, derived from fast pyrolysis of wood feedstocks, that exhibit properties of a preservative. The bio-oil may be used alone, in formulations with either a waterbased, or an oilbased, or a combination of a water based and an oil based preservatives. This invention also includes a method of preparing a wood preservative composition comprising, processing treated wood containing a preservative using a fast pyrolysis reactor, and obtaining the bio-oil fraction. The application of wood products with the bio-oil of the present invention is also disclosed.Type: GrantFiled: October 30, 1998Date of Patent: November 26, 2002Assignee: Ensyn Technologies, Inc.Inventors: Barry Freel, Robert G. Graham
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Patent number: 6172204Abstract: A composition that includes the reaction product of a lignin derivative and a reactant selected from the group consisting of alkylating agents, acylating agents, and combinations thereof, where the reaction product has a measurable cohesive strength, and a plasticizer in an amount sufficient to cause the composition to exhibit plastic deformation in response to an applied tensile stress.Type: GrantFiled: June 4, 1999Date of Patent: January 9, 2001Assignee: Regents of the University of MinnesotaInventors: Simo Sarkanen, Yan Li
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Patent number: 6054562Abstract: Lignin and polyether glycol produces a product which has a distinct melt point and melt viscosity. Polyether glycol has a plasticizing effect wherein the lignin can be thought of as the hard resin. When 20 parts of polyether glycol are processed with 80 parts of lignin a new material which has a melt point and a viscosity is created whereas lignin itself has no melt and flow characteristics. The new modified lignin can be cured with hexamine like a phenolic resin.Type: GrantFiled: February 25, 1999Date of Patent: April 25, 2000Inventor: Kenneth R. Kurple
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Patent number: 5773590Abstract: The separation of black liquor, containing lignin, from tall oil is enhanced by the addition of a separation aid. The separation aid is an alkylphenol-formaldehyde resin alkoxylate, a poly (proplyene oxide) ethoxylate, an alkanol amine condensate, or combination thereof.Type: GrantFiled: April 8, 1997Date of Patent: June 30, 1998Assignee: BetzDearborn Inc.Inventor: Paul R. Hart
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Patent number: 5749863Abstract: Skin wetness is minimized on overnight usage of a disposable absorbent article containing an acquisition and distribution member consisting essentially of C.sub.2 -C.sub.9 polycarboxylic acid crosslinked cellulosic fibers prepared in the presence of surfactant.Type: GrantFiled: July 11, 1996Date of Patent: May 12, 1998Assignee: The Procter & Gamble CompanyInventor: Michael Payne
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Patent number: 5608040Abstract: Polymers containing lignin and organic compounds are produced by polymerizing the lignin with organic compounds containing at least 3 carbon atoms as well as oxygen, nitrogen and/or multiple-linkage functions in the presence of radically oxidizing enzymes and of oxidation products constituting their substrate.Type: GrantFiled: July 6, 1995Date of Patent: March 4, 1997Assignee: Aloys H uttermannInventors: Aloys H uttermann, Oleg Milstein
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Patent number: 5484896Abstract: Individualized, esterified high lignin content cellulosic fibers containing intrafiber C.sub.2 -C.sub.9 polycarboxylic acid ester perform unexpectedly better in absorbent applications than lower lignin content esterified fibers from the same furnish.Type: GrantFiled: March 24, 1994Date of Patent: January 16, 1996Assignee: The Procter & Gamble CompanyInventors: Shahrokh A. Naieni, Carlisle M. Herron, Thomas R. Hanser
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Process for enhancing the hypocholesterolemic effect of edible pulp and the product obtained thereby
Patent number: 5202122Abstract: Process for enhancing the natural bile acid binding capacity of edible pulp material by either heating an aqueous slurry of the pulp material to at least 40.degree. C. and/or sequentially reacting pulp with a first reactant, such as sodium hydroxide, for activating the pendant hydroxyl groups on the polysaccharide components of the pulp material, a second reactant, such as chloroacetic acid, for carboxylating the activated pendant groups on the polysaccharides, and a third reactant, such as calcium hydroxide, for providing calcium ions which can ionically bond to the carboxylated pendant groups.Type: GrantFiled: April 9, 1991Date of Patent: April 13, 1993Assignee: Humanetics CorporationInventors: Frederic A. Graves, Ani Huang -
Patent number: 5066790Abstract: A method of producing prepolymeric materials from lignin is disclosed. The method uses lignin which has been hydroxyalkyl modified, such that the lignin is substantially non-phenolic and solvent soluble and/or liquid. The modified lignin is reacted with materials which yield prepolymers which may be polymerized according to known methods to produce useful polymers.Type: GrantFiled: January 4, 1990Date of Patent: November 19, 1991Assignees: Center for Innovative Technology, Virginia Polytechnic Institute and State UniversityInventors: Wolfgang G. Glasser, Willer De Oliveira, Stephen S. Kelley, Li S. Nieh
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Patent number: 4925923Abstract: A product comprising, a water insoluble lignin material, at neutral or acid pH, having chemically bound a sulfur(S) content from at least 9.5%, and a phosphorus(P) content from 3.3 to 10%. At least 50% by weight of the S and P content is thiophosphate. In said lignin material the mole ratio S/P is at least 1.8 that of S to aromatic unit (S/Ar) is greater than 0.7, and the P/Ar ratio is from 0.3 to 0.8. The lignin material has chelating capacities for gold at pH 2 of at least 2.2 millimoles per gram of lignin material. On IR analysis the lignin material has infra-red absorption bands evidencing P.dbd.S, P--S or Ar--S, P--O--Ar, aromatic, CH.sub.2 --S, and P--O--C groups in the vicinity of 730-750, 640-670, 1080-1110, 1490-1510, 820-845, and 965-995 cm.sup.-1, respectively. In the absence of interferring IR bands, the sum of the intensity of the bands in the vicinity of 640-670 cm.sup.-1 and 730-750 cm.sup.-1 over the intensity of the band in the vicinity of 1080-1110 cm.sup.-1 is greater than 1.Type: GrantFiled: May 10, 1989Date of Patent: May 15, 1990Assignee: Domtar Inc.Inventors: Manssur Yalpani, Leon Magdzinski
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Patent number: 4918167Abstract: A method of producing prepolymeric materials from lignin is disclosed. The method uses lignin which has been hydroxyalkyl modified, such that the lignin is substantially non-phenolic and solvent soluble and/or liquid. The modified lignin is reacted with materials which yield prepolymers which may be polymerized according to known methods to produce useful polymers.Type: GrantFiled: April 19, 1988Date of Patent: April 17, 1990Assignee: Center for Innovative TechnologyInventors: Wolfgang G. Glasser, Willer De Oliveira, Stephen S. Kelley, Li S. Nieh
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Patent number: 4857638Abstract: A product comprising lignin material having a N-content of at least 1.86% and a sulfur content of at least 3.1%, an IR in the vicinity of 1550 to 1670 cm.sup.-1 having a peak width of at least 60 cm.sup.-1. The product is also directed to such products being cross-linked and which are most suitable as chelating agents in basic medium. The product may also be used as flame retardant, for agricultural and other end uses. The invention is also directed at a method of making the above product which comprises heating a lignin containing material with thiourea H.sub.2 N--C(S)--NH.sub.2 : for example by heating in a solvent or melting.Type: GrantFiled: December 28, 1987Date of Patent: August 15, 1989Assignee: Domtar Inc.Inventors: Manssur Yalpani, Leon Magdzinski
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Patent number: 4739041Abstract: The invention is a method of producing surfactants from lignin which comprises subjecting lignin to two reactions, alkylation with an alkyl chain having about 3 to about 24 carbon atoms at phenolic sites, and oxidation sufficient to break the lignin into smaller polymeric and monomeric units. The invention also includes using these lignin surfactants in surfactant floods for enhanced oil recovery.Type: GrantFiled: December 29, 1986Date of Patent: April 19, 1988Assignee: Texaco Inc.Inventors: Lawrence R. Morrow, Michael G. DaGue, Lawrence E. Whittington
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Patent number: 4534771Abstract: A process for preparing sulfonated lignins suitable for use as dispersants and additives in dye compositions wherein sulfonated lignins are post-sulfonation crosslinked with a crosslinking agent of the aldehyde, epoxide, or polyhalide type at a pH range of between about 6.1 to 9 to selectively crosslink low molecular weight sizes of the sulfonated lignins to provide improved heat stability and dispersibility of the sulfonated lignins in dye compositions. The invention also concerns disperse and vat dye compositions, and printing gels, containing the sulfonated lignins as a dispersing agent or additive.Type: GrantFiled: March 21, 1984Date of Patent: August 13, 1985Assignee: Westvaco CorporationInventor: Peter Dilling