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)
  • Patent number: 10717873
    Abstract: 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: Grant
    Filed: March 20, 2017
    Date of Patent: July 21, 2020
    Assignee: Stora Enso OYJ
    Inventors: Ashar Zafar, Dimitri Areskogh, Jesper Ekström
  • Patent number: 10030147
    Abstract: 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: Grant
    Filed: December 16, 2014
    Date of Patent: July 24, 2018
    Assignee: Ren Fuel K2B AB
    Inventors: Joseph Samec, Joakim Löfstedt, Christian Dahlstrand, Alexander Orebom, Supaporn Sawadjoon
  • Patent number: 8987428
    Abstract: 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: Grant
    Filed: March 7, 2012
    Date of Patent: March 24, 2015
    Assignee: Empire Technology Development LLC
    Inventor: Georgius Abidal Adam
  • Publication number: 20150051384
    Abstract: 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: Application
    Filed: January 31, 2013
    Publication date: February 19, 2015
    Applicant: TITAN WOOD LIMITED
    Inventors: Jonathan Philip Alexander, Hendrikus Petrus Maria Bongers
  • Publication number: 20140235838
    Abstract: 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: Application
    Filed: February 20, 2013
    Publication date: August 21, 2014
    Applicant: Wisconsin Alumni Research Foundation
    Inventors: Shannon S. Stahl, Alireza Rahimi
  • Publication number: 20130180927
    Abstract: 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: Application
    Filed: January 13, 2012
    Publication date: July 18, 2013
    Applicant: GENERAL ELECTRIC COMPANY
    Inventors: Hongchen Dong, Wenqing Peng, Larry Neil Lewis
  • Publication number: 20120012035
    Abstract: 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: Application
    Filed: March 19, 2010
    Publication date: January 19, 2012
    Applicant: SIKA TECHNOLOGY AG
    Inventors: Norman Blank, Irene Schober, Philipp Rudolf Von Rohr, Tobias Voitl
  • Publication number: 20110308810
    Abstract: 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: Application
    Filed: December 15, 2010
    Publication date: December 22, 2011
    Inventors: Kristoffer K. Stokes, David Soane, Michael C. Berg, Kevin T. Petersen, William A. Mowers
  • Publication number: 20100331531
    Abstract: Methods of making esterified lignocellulosic materials and resulting compositions and articles are disclosed.
    Type: Application
    Filed: June 17, 2010
    Publication date: December 30, 2010
    Applicant: Eastman Chemical Company
    Inventor: John Peter Mykytka
  • Publication number: 20100204368
    Abstract: 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: Application
    Filed: January 8, 2010
    Publication date: August 12, 2010
    Inventors: David Andrew Benko, Bruce Raymond Hahn, Martin Paul Cohen, Shawn Matthew Dirk, Kirsten Nicole Cicotte
  • Publication number: 20100152428
    Abstract: 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: Application
    Filed: December 12, 2008
    Publication date: June 17, 2010
    Applicant: WEYERHAEUSER COMPANY
    Inventors: Angela P. Gifford, John A. Westland, Amar N. Neogi, Karen D. Ragan
  • Patent number: 7691982
    Abstract: 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: Grant
    Filed: September 22, 2005
    Date of Patent: April 6, 2010
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Takashi Tomita, Tsuyoshi Hirata
  • Patent number: 6572859
    Abstract: 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: Grant
    Filed: October 26, 2000
    Date of Patent: June 3, 2003
    Assignees: Pharmacia Diagnostics AB
    Inventors: Rudolf Valenta, Susanne Vrtala, Sabine Stummfoll, Hans Grönlund, Monika Grote, Luca Vangelista, Annalisa Pastore, Wolfgang R. Sperr, Peter Valent, Dietrich Kraft
  • Patent number: 6485841
    Abstract: 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: Grant
    Filed: October 30, 1998
    Date of Patent: November 26, 2002
    Assignee: Ensyn Technologies, Inc.
    Inventors: Barry Freel, Robert G. Graham
  • Patent number: 6172204
    Abstract: 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: Grant
    Filed: June 4, 1999
    Date of Patent: January 9, 2001
    Assignee: Regents of the University of Minnesota
    Inventors: Simo Sarkanen, Yan Li
  • Patent number: 6054562
    Abstract: 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: Grant
    Filed: February 25, 1999
    Date of Patent: April 25, 2000
    Inventor: Kenneth R. Kurple
  • Patent number: 5773590
    Abstract: 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: Grant
    Filed: April 8, 1997
    Date of Patent: June 30, 1998
    Assignee: BetzDearborn Inc.
    Inventor: Paul R. Hart
  • Patent number: 5749863
    Abstract: 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: Grant
    Filed: July 11, 1996
    Date of Patent: May 12, 1998
    Assignee: The Procter & Gamble Company
    Inventor: Michael Payne
  • Patent number: 5608040
    Abstract: 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: Grant
    Filed: July 6, 1995
    Date of Patent: March 4, 1997
    Assignee: Aloys H uttermann
    Inventors: Aloys H uttermann, Oleg Milstein
  • Patent number: 5484896
    Abstract: 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: Grant
    Filed: March 24, 1994
    Date of Patent: January 16, 1996
    Assignee: The Procter & Gamble Company
    Inventors: Shahrokh A. Naieni, Carlisle M. Herron, Thomas R. Hanser
  • Patent number: 5202122
    Abstract: 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: Grant
    Filed: April 9, 1991
    Date of Patent: April 13, 1993
    Assignee: Humanetics Corporation
    Inventors: Frederic A. Graves, Ani Huang
  • Patent number: 5066790
    Abstract: 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: Grant
    Filed: January 4, 1990
    Date of Patent: November 19, 1991
    Assignees: Center for Innovative Technology, Virginia Polytechnic Institute and State University
    Inventors: Wolfgang G. Glasser, Willer De Oliveira, Stephen S. Kelley, Li S. Nieh
  • Patent number: 4925923
    Abstract: 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: Grant
    Filed: May 10, 1989
    Date of Patent: May 15, 1990
    Assignee: Domtar Inc.
    Inventors: Manssur Yalpani, Leon Magdzinski
  • Patent number: 4918167
    Abstract: 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: Grant
    Filed: April 19, 1988
    Date of Patent: April 17, 1990
    Assignee: Center for Innovative Technology
    Inventors: Wolfgang G. Glasser, Willer De Oliveira, Stephen S. Kelley, Li S. Nieh
  • Patent number: 4857638
    Abstract: 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: Grant
    Filed: December 28, 1987
    Date of Patent: August 15, 1989
    Assignee: Domtar Inc.
    Inventors: Manssur Yalpani, Leon Magdzinski
  • Patent number: 4739041
    Abstract: 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: Grant
    Filed: December 29, 1986
    Date of Patent: April 19, 1988
    Assignee: Texaco Inc.
    Inventors: Lawrence R. Morrow, Michael G. DaGue, Lawrence E. Whittington
  • Patent number: 4534771
    Abstract: 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: Grant
    Filed: March 21, 1984
    Date of Patent: August 13, 1985
    Assignee: Westvaco Corporation
    Inventor: Peter Dilling