Processes Utilizing An Organic Solvent Or A Compound Having Alcoholic Hydroxy Bonded Directly To An Acyclic Carbon, Or Product Thereof Patents (Class 530/507)
  • Publication number: 20110313141
    Abstract: There is described a method of processing biomass which comprises the digestion of biomass material in an aqueous solvent system subjected to ultrasonic waves and separating the biomass into its constituents of lignin, hemicellulose and cellulose. There is also described a system for the processing of biomass which comprises the digestion of biomass material in an aqueous solvent system subjected to ultrasonic waves and separating the biomass into ins constituents of lignin, hemicellulose and cellulose.
    Type: Application
    Filed: November 23, 2009
    Publication date: December 22, 2011
    Applicant: BIO-SEP LIMITED
    Inventor: Stephen Brooks
  • Patent number: 8053566
    Abstract: 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: Grant
    Filed: September 2, 2008
    Date of Patent: November 8, 2011
    Assignee: Vertichem Corporation
    Inventors: Helene Belanger, Ross L. Prestidge, Tony James Lough, James D. Watson
  • Publication number: 20110160442
    Abstract: The invention relates to a method for the fractionation of knotwood extract, which has been obtained by extraction of knotwood with a hydrophilic solvent. The hydrophilic extract is extracted with a lipophilic solvent to remove lipophilic impurities. The invention also relates to the use of a liquid-liquid extraction for the purification of hydrophilic knotwood extract. The present process provides a purified knotwood extract, which contains more than 90% lignans, flavonoids and stilbenes and less than 10% impurities selected from resin acids, fatty acids, sterols, juvabiones, triglycerides and combinations thereof.
    Type: Application
    Filed: June 18, 2009
    Publication date: June 30, 2011
    Inventors: Suvi Pietarinen, Ulf Hotanen
  • Publication number: 20110129886
    Abstract: Non-food plant biomass is subjected to hot-water extraction in a pressurized vessel at an elevated temperature up to about 250° C. and at a pH below about 7.0, to yield an aqueous extract containing hemicellulosic components, other wood-derived compounds, and a lignocellulosic residue. The separated aqueous extract or liquor is purified and concentrated through a multi-step process producing fermentable sugars. At each stage, inhibitory chemicals such as acetic acid, lignin, and furfural are separated and eventually recovered as commercial chemicals. The lignocellulosic residue may be further processed, as a material with enhanced resistance to sorption of water, for manufacture of improved pulp and paper, construction materials, pellet fuel, and/or other useful products.
    Type: Application
    Filed: August 5, 2010
    Publication date: June 2, 2011
    Inventors: Joel R. Howard, Thomas E. Amidon, Shijie Liu, Christopher D. Wood
  • Publication number: 20110054154
    Abstract: A thermoplastic material made from lignin, polyol and a melting point reducer where the melting point reducer is miscible in the specific polyol employed and where the lignin, polyol and melting point reducer are all miscible when in their melted state.
    Type: Application
    Filed: August 31, 2009
    Publication date: March 3, 2011
    Applicant: Weyerhaeuser NR Company
    Inventors: DAVID W. PARK, Amar N. Neogi, Ludwig Furtner, JR.
  • Publication number: 20110028426
    Abstract: A process for dewatering biomass material comprising polysaccharide and water. The process comprises wetting the biomass material with a wetting composition comprising an alcohol to form a biomass slurry comprising wetted biomass material and a liquid component, mechanically separating a portion of the liquid component from the biomass slurry, and mechanically separating at least a portion of the water from the wetted biomass material. A process for extracting polysaccharide from the biomass material and a dewatered biomass material are also disclosed.
    Type: Application
    Filed: July 28, 2009
    Publication date: February 3, 2011
    Applicant: CP KELCO APS
    Inventors: Jens Eskil Trudsoe, Helle Bech Olsen, Mogens Andersen
  • Publication number: 20110003352
    Abstract: A method for the fractionation of lignocellulosic materials into reactive chemical feedstock in a batch or semi continuous process by the stepwise treatment with aqueous aliphatic alcohols in the presence of sulfur dioxide or acid. Lignocellulosic material is fractionated in a fashion that cellulose is removed as pulp, or converted to esterified cellulose, cooking chemicals are reused, lignin is separated in the forms of reactive native lignin and reactive lignosulfonates and hemicelluloses are converted into fermentable sugars, while fermentation inhibitors are removed. In an integrated vapor compression stripper and evaporator system, aliphatic alcohol is removed from a liquid stream and the resulting stream is concentrated for further processing.
    Type: Application
    Filed: June 12, 2007
    Publication date: January 6, 2011
    Applicant: AMERICAN PROCESS, INC.
    Inventors: Theodora Retsina, Vesa Pylkkanen, Rolf Ryham
  • 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: 20100305244
    Abstract: The present invention provides derivatives of native lignin having a certain aliphatic hydroxyl content. Surprisingly, it has been found that consistent and predictable antioxidant activity may be provided by selecting for derivatives of native lignin having a certain aliphatic hydroxyl content.
    Type: Application
    Filed: February 15, 2010
    Publication date: December 2, 2010
    Inventors: Mikhail Yurevich Balakshin, Alex Berlin, Humbert Thomas Dellicolli, Chadrick Adam Nathaniel Jordan Grunert, Vera Maximenko Gutman, Darwin Ortiz, Edward Kendall Pye
  • Publication number: 20100305242
    Abstract: The present invention provides hardwood derivatives of native lignin having a certain aliphatic hydroxyl content. Surprisingly, it has been found that consistent and predictable antioxidant activity may be provided by selecting for derivatives of native lignin having a certain aliphatic hydroxyl content.
    Type: Application
    Filed: February 15, 2010
    Publication date: December 2, 2010
    Inventors: Mikhail Yurevich Balakshin, Alex Berlin, Humbert Thomas Dellicolli, Chadrick Adam Nathaniel Jordan Grunert, Vera Maximenko Gutman, Darwin Ortiz, Edward Kendall Pye
  • Publication number: 20100305243
    Abstract: The present invention provides softwood derivatives of native lignin having a certain aliphatic hydroxyl content. Surprisingly, it has been found that consistent and predictable antioxidant activity may be provided by selecting for derivatives of native lignin having a certain aliphatic hydroxyl content.
    Type: Application
    Filed: February 15, 2010
    Publication date: December 2, 2010
    Inventors: Mikhail Yurevich Balakshin, Alex Berlin, Humbert Thomas Dellicolli, Chadrick Adam Nathaniel Jordan Grunert, Vera Maximenko Gutman, Darwin Ortiz, Edward Kendall Pye
  • Publication number: 20100249390
    Abstract: A new lignin degradation product, a method for producing the same, and methods for producing a saccharide raw material and a monosaccharide raw material are provided. The method for producing the new lignin degradation product includes: (a first step) mixing 100 parts by mass of a powder, obtained by pulverizing a lignocellulosic raw material and defatting the resulting powder with an organic solvent, with aqueous hydrogen peroxide in an amount of 20 to 400 parts by mass in terms of hydrogen peroxide and heating the mixture for 5 to 120 minutes at a pressure of 0.1 to 1.5 MPa and a temperature of 80 to 200° C. while irradiating the mixture with microwaves; (a second step) separating insoluble matter from the aqueous hydrogen peroxide; (a third step) extracting the insoluble matter with a solvent to produce an extract; and (a fourth step) distilling the solvent away from the extract to yield a solubilized lignin as a residue.
    Type: Application
    Filed: October 15, 2008
    Publication date: September 30, 2010
    Applicant: NIPPON STEEL CHEMICAL CO., LTD.
    Inventors: Jun-ichi Azuma, Tetsuo Sakamoto, Kiyotaka Onishi
  • Publication number: 20100136642
    Abstract: 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: Application
    Filed: December 15, 2009
    Publication date: June 3, 2010
    Applicant: BIOJOULE LIMITED
    Inventors: Helene BELANGER, Ross L. PRESTIDGE, Tony James LOUGH, James D. WATSON, Clare ELTON, Alan McFARLANE, Mohammed Mehdi FARID, John CHEN
  • Publication number: 20090069550
    Abstract: 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: Application
    Filed: September 2, 2008
    Publication date: March 12, 2009
    Applicant: BIOJOULE LIMITED
    Inventors: Helene BELANGER, Ross L. PRESTIDGE, Tony James LOUGH, James D. WATSON
  • Publication number: 20090062516
    Abstract: 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: Application
    Filed: September 2, 2008
    Publication date: March 5, 2009
    Applicant: BIOJOULE LIMITED
    Inventors: Helene BELANGER, Ross L. PRESTIDGE, Tony James LOUGH, James D. WATSON
  • Patent number: 6806356
    Abstract: A process for extracting secoisolariciresinol diglycoside (SDG) from de-fatted flaxseed is described. The process comprises contacting defatted flaxseed with an extraction solvent of acetone and water, extracting the de-fatted flaxseed with the extraction solvent to extract SDG-containing compounds, removal of solvents, followed by alkaline hydrolysis of the extract to liberate free SDG or its salts.
    Type: Grant
    Filed: April 2, 2003
    Date of Patent: October 19, 2004
    Assignee: Wiley Organics, Inc.
    Inventors: Thomas A. Dobbins, David B. Wiley
  • Publication number: 20030216553
    Abstract: A process for extracting secoisolariciresinol diglycoside (SDG) from de-fatted flaxseed is described. The process comprises contacting defatted flaxseed with an extraction solvent of acetone and water, extracting the de-fatted flaxseed with the extraction solvent to extract SDG-containing compounds, removal of solvents, followed by alkaline hydrolysis of the extract to liberate free SDG or its salts.
    Type: Application
    Filed: April 2, 2003
    Publication date: November 20, 2003
    Inventors: Thomas A. Dobbins, David B. Wiley
  • Patent number: 6593460
    Abstract: The invention relates to biologically degradable lignin graft polymers comprised of lignin and ethylenically unsaturated monomers which are formed by an enzymatically catalyzed polymerization method in the presence of organic peroxides. The polymerizates are suited, for example, for utilization as absorbers for water and aqueous liquids, as coagulants and thickeners, as water softeners and as dispersing agents.
    Type: Grant
    Filed: October 12, 2000
    Date of Patent: July 15, 2003
    Assignee: Stockhausen GmbH & Co KG
    Inventors: Aloys Hüttermann, Carsten Mai
  • Publication number: 20030055227
    Abstract: Process for obtaining lignan from plant material by extraction with an extraction solvent and separation of the liquid fraction from the plant material. The separated liquid fraction containing the lignan product is subjected to further processing to remove cyanogenic sugars and other impurities. The resulting lignan containing product may be formulated for the treatment of various conditions, such as cancer, diabetes, hypertension, lupus, and atherosclerosis.
    Type: Application
    Filed: March 20, 2002
    Publication date: March 20, 2003
    Inventors: Rishi Shukla, Ahmad K. Hilaly, Kevin M. Moore
  • Patent number: 6335373
    Abstract: A novel process for the production of the natural antioxidant, carnosic acid, by extracting it from rosemary leaves with an aqueous solution of a lower alkyl alcohol in the presence of a water soluble acid is described. The extraction of the carnosic acid is very selective, i.e. very few other chemicals such as pro-oxidants from the plant are extracted. Furthermore, a method for the stabilization of the extracted acid from decomposition and a method of preparing the acid in high concentration are described.
    Type: Grant
    Filed: January 18, 2000
    Date of Patent: January 1, 2002
    Assignee: Lycored Natural Products Industries, Ltd.
    Inventors: Gil Ben-Yosef, Arkady Garbar
  • Patent number: 6264853
    Abstract: A substanially pure chemically bound complex is derived from flax containing secoisolariciresinol diglucoside, cinnamic acid glycosides and hydroxy methyl glutaric acid. The complex is obtained by preparing an aqueous aliphatic alcoholic extract from flax and subjecting this aqueous extract to ultrafiltration whereby low molecular weight species remain with a filtrate and higher molecular weight species comprising the separated complex are retained.
    Type: Grant
    Filed: June 21, 1999
    Date of Patent: July 24, 2001
    Assignee: Agriculture and Agri-Food Canada
    Inventors: Neil D. Westcott, David Paton
  • Patent number: 6239198
    Abstract: The invention proposes a process which enables separation of aromatic polymers which can be precipitated by acidification, as can be found especially in waste water from cellulose production, from an alkaline solution in a reliable manner and in pure form. To achieve good separation capacity, especially by filtration, it is proposed that the polymers be precipitated by reducing the pH at a relatively low temperature, typically between 15 and 60° C., and the dispersion be subsequently reheated until it passes into filterable form, typically between 50 and 95° C. The product separated in this way for example by filtration can be washed and can be dried at a high temperature, especially up to 110° C., without becoming black.
    Type: Grant
    Filed: September 1, 1999
    Date of Patent: May 29, 2001
    Assignee: Granit S.A.
    Inventors: Alfred Abächerli, Frank Doppenberg
  • Patent number: 6072015
    Abstract: A method is provided for producing a painted article comprising: (a) preparing a lignin solution comprising lignin and a dye or pigment; (b) mixing the lignin solution with a phenol oxidizing enzyme; (c) incubating the mixture from said step (b) under conditions and for a time sufficient to form a solution of a desired viscosity; (d) contacting or spreading the mixture from the step (c) on an article to be painted; and (e) allowing the mixture to set onto the article by subjecting the article to conditions and for a time sufficient to form a paint on the surface of the article.
    Type: Grant
    Filed: December 8, 1998
    Date of Patent: June 6, 2000
    Assignee: Genencor International, Inc.
    Inventors: Rob Bolle, Wolfgang Aehle
  • 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: 6013774
    Abstract: In this disclosure, there are provided materials which completely degrade in the environment far more rapidly than pure synthetic plastics but which possesses the desirable properties of a thermoplastic: strength, impact resistance, stability to aqueous acid or base, and deformation at higher temperatures. There is provided a method for using the degradable plastic materials in preparing strong, moldable solids. There is further provided a method of making and applications for macromolecular, surface active agents that change the wetting behavior of lignin-containing materials. These surface active agents are used to provide a method of making and applications for synthetic polymers coupled to pieces of a vascular plant using macromolecular surface active agents.
    Type: Grant
    Filed: September 29, 1998
    Date of Patent: January 11, 2000
    Inventors: John J. Meister, Meng-Jiu Chen
  • Patent number: 5852069
    Abstract: In this disclosure, there are provided materials which completely degrade in the environment far more rapidly than pure synthetic plastics but which possesses the desirable properties of a thermoplastic: strength, impact resistance, stability to aqueous acid or base, and deformation at higher temperatures. There is provided a method for using the degradable plastic materials in preparing strong, moldable solids. There is further provided a method of making and applications for macromolecular, surface active agents that change the wetting behavior of lignin-containing materials. These surface active agents are used to provide a method of making and applications for synthetic polymers coupled to pieces of a vascular plant using macromolecular surface active agents.
    Type: Grant
    Filed: October 2, 1997
    Date of Patent: December 22, 1998
    Inventors: John J. Meister, Meng-Jiu Chen
  • Patent number: 5756098
    Abstract: Methods and apparatus are provided for the recovery of organic compounds from fibrous plant materials. Organic compounds which can be recovered from the fibrous plant materials include plant metabolites, such as arabinogalactan and phenols, which can be isolated from the wood, for example, of the Western Larch and Tamarack tree varieties. In addition to the recovery of organic compounds from wood, fibrous wood products also may be isolated, in the form of a clean fiber that can be used, for example, as raw material in wood processing applications or in the manufacture of high quality paper products. In one embodiment, a fibrous plant material first is compressed, to recover a liquid exudate and a first pressed plant fiber product. Optionally, the fibrous plant material, such as wood particles, is compressed in the substantial absence of any added solvent, to produce a pure normal liquid exudate and a first pressed plant product.
    Type: Grant
    Filed: December 12, 1995
    Date of Patent: May 26, 1998
    Assignees: The University of Montana, Larex International, Inc., Crown Iron Works Company
    Inventors: Christopher H. Price, Dale Hedtke, Geoffrey N. Richards, Michael S. Tempesta
  • Patent number: 5741875
    Abstract: In this disclosure, there are provided materials which completely degrade in the environment far more rapidly than pure synthetic plastics but which possesses the desirable properties of a thermoplastic: strength, impact resistance, stability to aqueous acid or base, and deformation at higher temperatures. There is provided a method for using the degradable plastic materials in preparing strong, moldable solids. There is further provided a method of making and applications for macromolecular, surface active agents that change the wetting behavior of lignin-containing materials. These surface active agents are used to provide a method of making and applications for synthetic polymers coupled to pieces of a vascular plant using macromolecular surface active agents.
    Type: Grant
    Filed: March 8, 1995
    Date of Patent: April 21, 1998
    Inventors: John J. Meister, Meng-Jiu Chen
  • Patent number: 5705618
    Abstract: A process is described for extracting lignans from flaxseed which comprises contacting a substantially oil-free flaxseed meal with an aliphatic alcohol solvent, e.g. a mixture of methanol or ethanol with water, to extract lignans into the alcohol solvent and separating residual solids from the lignan-rich alcohol solvent. The lignan-rich alcohol solvent is concentrated by removing solvent therefrom and the lignan concentrate obtained is subjected to a base-catalyzed hydrolysis to liberate lignans therefrom in a non-complexed form. Thereafter, the hydrolyzed concentrate is subjected to either a liquid/liquid partition, e.g. by an ethyl acetate/water system, or anion exchange to further enrich the lignans and the lignan-enriched solution thus obtained is subjected to chromatographic separation to isolate lignans at a purity of greater than 90 percent. The lignan, secoisolariciresinol diglucoside, was found in amounts of up to 20 mg per gram of defatted flaxseed.
    Type: Grant
    Filed: March 31, 1995
    Date of Patent: January 6, 1998
    Assignee: Agriculture and Agri-Food Canada
    Inventors: Neil D. Westcott, Alister D. Muir
  • 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: 5446133
    Abstract: A process for producing an oxidized lignosulfonate composition comprising admixing a lignosulfonate and nitric acid such that the amount of acid comprises from about 35% to about 100% by weight of dry solids of the lignosulfonate, and reacting said mixture for a time sufficient to form the oxidized lignosulfonate composition.
    Type: Grant
    Filed: March 2, 1994
    Date of Patent: August 29, 1995
    Assignee: LignoTech USA, Inc.
    Inventor: William J. Detroit
  • Patent number: 5288857
    Abstract: The invention relates to a lignin preparation prepared from black liquor derived from an alkali delignification process, such as the sulphate process, soda process or polysulphide process. The lignin preparation comprises mainly lignin and at least the major part of the sodium content of the lignin separated from the black liquor deriving from such processes has been replaced with calcium, therewith to provide a lignin preparation having improved properties which render the preparation more suitable for use as fuel.
    Type: Grant
    Filed: February 16, 1993
    Date of Patent: February 22, 1994
    Assignee: Ligno Tech Sweden AB
    Inventors: Wilhelm Aarsrud, Hans Bergstrom, Ingemar Falkehag
  • Patent number: 5223258
    Abstract: An antiviral medicinal composition having spent liquor from kraft pulping and/or processed products thereof (kraft lignin, sulfomethylated and/or sulfopropylated kraft lignin) as major constituents, are effective agents in therapeutic and/or preventive methods against AIDS.
    Type: Grant
    Filed: January 11, 1990
    Date of Patent: June 29, 1993
    Assignee: Sanyo-Kokusaku Pulp Co., Ltd.
    Inventors: Makoto Machida, Makoto Yashiro, Kunichika Murakami
  • Patent number: 5196460
    Abstract: A tackifier composition for use in rubber compounds is disclosed. The tackifier comprises a pure lignin with a water solubility of up to 1% by weight and a carbohydrate level of less than 50% by weight. In another embodiment of the invention, the pure lignin functions as both a tackifier and an antioxidant. In yet another preferred embodiment of the invention, the improved tackifier produces synergistic results when blended with a commercial tackifier, and the antioxidant likewise yields synergistic results when mixed with a commercial antioxidant.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: March 23, 1993
    Assignee: Repap Technologies Inc.
    Inventors: Jairo H. Lora, Michael J. Trojan, William H. Klingensmith
  • Patent number: 5177169
    Abstract: Lignin, or a lignin derived material, which has been significantly demethylated (e.g., the demethylated lignin found in the raffinate produced as a by-product of dimethyl sulfide production which can be carried out using the spent liquor from wood pulping operations) can be isolated by a process wherein an organic solvent is added to a lignin-containing aqueous solution. The organic solvent is typically a polar, and at least a partially water-immiscible substance such as, for example, ethyl acetate. The resulting lignin-containing aqueous solution/organic solvent mixture is acidified to produce a water layer which is discarded and an organic solvent layer which contains the demethylated lignin. Upon its recovery, the demethylated lignin is dissolved in an alkaline solution to which an aldehyde source is added to produce a resol-type resin. The aldehyde source may be formaldehyde in solution, paraformaldehyde, hexamethylenetetramine, or other aldehydes including acetaldehyde, furfural, and their derivatives.
    Type: Grant
    Filed: May 29, 1991
    Date of Patent: January 5, 1993
    Assignee: Colorado State University Research Foundation
    Inventor: Herbert A. Schroeder
  • Patent number: 5116969
    Abstract: The invention is a very highly refined arabinogalactan gum falling within the molecular weight range of 6,000-2,500,000 and having a tannic acid equivalent of less than about 0.5 mg/g. The preferred product will have a molecular weight within the range of 6,000-1,300,000 and tannic acid equivalent no higher than about 0.25. The product is nearly colorless and is tasteless and odorless. it is prepared by first making a crude water extract of a natural source such as larch wood. This extract is next refined by the addition of an active MgO to precipitate the bulk of the lignans and iron containing compounds. Following that it is processed through a membrane no larger than about 0.45 .mu.m to remove any species having molecular weights in excess of about 2,500,000. The permeate may then be treated on successively smaller membranes down to about 6,000 daltons.
    Type: Grant
    Filed: April 26, 1990
    Date of Patent: May 26, 1992
    Assignee: Larex International, Inc.
    Inventors: Mark F. Adams, Melvin R. Knudson
  • Patent number: 5102991
    Abstract: Lignin sulfonates are converted into sulfonic acid esters by blocking free phenolic hydroxyl groups on the lignin sulfonates from reaction with a suitable protective group, subjecting the blocked lignin sulfonate in aqueous solution to ion exchange to produce the free sulfonic acid thereof, exchanging the aqueous solvent into a polar organic solvent, such as isopropanol, and reacting the sulfonic acid derivative in the polar organic solvent with a saturated or unsaturated aliphatic epoxide, preferably an alkylene oxide. The resulting sulfonic acid ester adduct may be isolated and purified from the reactants using solvent extraction. Lignin sulfonic acid ester adducts are produced that are soluble in a variety of organic solvents and insoluble in water.
    Type: Grant
    Filed: April 11, 1990
    Date of Patent: April 7, 1992
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventors: Wolfgang Glasser, Kaliprasanna Dhara
  • Patent number: 5026808
    Abstract: Lignin, or a lignin derived material, which has been significantly demethylated (e.g., the demethylated lignin found in the raffinate produced as a by-product of dimethyl sulfide production which can be carried out using the spent liquor from wood pulping operations) can be isolated by a process wherein an organic solvent is added to a lignin-containing aqueous solution. The organic solvent is typically a polar, and at least a partially water-immiscible substance such as, for example, ethyl acetate. The resulting lignin-containing aqueous solution/organic solvent mixture is acidified to produce a water layer which is discarded and an organic solvent layer which contains the demethylated lignin. Upon its recovery, the demethylated lignin is dissolved in an alkaline solution to which an aldehyde source is added to produce a resol-type resin. The aldehyde source may be formaldehyde in solution, paraformaldehyde, hexamethylenetetramine, or other aldehydes including acetaldehyde, furfural, and their derivatives.
    Type: Grant
    Filed: April 3, 1989
    Date of Patent: June 25, 1991
    Assignee: Colorado State University Research Foundation
    Inventor: Herbert A. Schroeder
  • Patent number: 5021531
    Abstract: Lignin, or a lignin derived material, which has been significantly demethylated (e.g., the demethylated lignin found in the raffinate produced as a by-product of dimethyl sulfide production which can be carried out using the spent liquor from wood pulping operations) can be isolated by a process wherein an organic solvent is added to a lignin-containing aqueous solution. The organic solvent is typically a polar, and at least a partially water-immiscible substance such as, for example, ethyl acetate. The resulting lignin-containing aqueous solution/organic solvent mixture is acidified to produce a water layer which is discarded and an organic solvent layer which contains the demethylated lignin. Upon its recovery, the demethylated lignin is preferably dried and stored until it is used (along with an alkali, an aldehyde and an adhesive filler) in compounding an adhesive of the type generally used in the manufacture of plywood.
    Type: Grant
    Filed: February 20, 1990
    Date of Patent: June 4, 1991
    Assignee: Colorado State University Research Foundation
    Inventor: Herbert A. Schroeder
  • Patent number: 5010156
    Abstract: A lignin-modified phenol-formaldehyde resin for use as an adhesive for particulate wood products is disclosed which is prepared by reacting phenol and formaldehyde with an aqueous alkaline solution of an organosolv lignin. The organosolv lignin used in the formation of the resin is obtained from a pulping liquor prepared from particulate wood material from hardwood trees, aqueous polar organic solvent, and an acid catalyst. The resin allows for replacement of phenol or organosolv lignin at a level of up to 40% without detrimentally affecting its performance in terms of bonding strength or durability. The resin of the present invention is also superior to prior art lignin-modified resins in that it is low in sulfate, ash and sulfur residues, and thus will not give off distracting or harmful sulfur odors during resin preparation or hot-pressing of the adhesive and is unaffected and not solubilized by water.
    Type: Grant
    Filed: March 12, 1990
    Date of Patent: April 23, 1991
    Assignee: Eastman Kodak Company
    Inventors: Phillip M. Cook, Steven L. Hess
  • Patent number: 4966650
    Abstract: The chemical components of lignocellulosic material which have been dissociated by a steam explosion process can be extracted from the mixture of components using a solvent extraction process. The solvents are water, alcohol and a mild caustic in that order, or the alcohol step can be by-passed and only water and caustic are used. The caustic is a stronger solvent and it will extract the alcohol solubles along with the caustic only solubles. The eluant from the these extractions contains a range of lignin derived substances, which have different applications, such as thermoplastic and thermosetting characteristics. This invention describes a method for partitioning these lignin components into reproducible fractions having definable characteristics for particular applications. For instance, many copolymer applications require a thermosetting only fraction of the lignin. Other applications require a thermoplastic only lignin.
    Type: Grant
    Filed: September 19, 1988
    Date of Patent: October 30, 1990
    Inventors: Edward A. DeLong, George S. Ritchie
  • Patent number: 4908098
    Abstract: The chemical components of lignocellulosic material that have been dissociated by a stream explosion process can be extracted from the mixture of components using a solvent extraction process. The dissociated lignocellulosic material is put in a column and the substances which are soluble in water, alcohol and caustic are leached out of the mixture by solvent extraction with relatively small volumes of those solvents. No agitation is used. Substantially pure cellulose remains in the column and it can be bleached before removal from the column.
    Type: Grant
    Filed: April 18, 1989
    Date of Patent: March 13, 1990
    Assignee: Tigney Technology Inc.
    Inventors: Edward A. DeLong, Edward P. DeLong, George S. Ritchie, W. Alan Rendall
  • Patent number: 4826566
    Abstract: A method of rapidly and efficiently treating ligno-cellulosic material for removal of lignin and other non-carbohydrates as well as non-cellulosic carbohydrates from cellulosic matter. Such material is first impregnated with a liquor which is a reaction product obtained by mixing triethyleneglycol with an arylsulfonic or other organic acid. The impregnated material is then rapidly heated by microwaving or application of rf energy to a temperature between about 119 degrees Centigrade to 130 degrees Centigrade and maintained at that temperature for only two to five minutes to reduce the effects of hydrolysis. Thereafter, conventional filtration and washing techniques are applied to achieve a residue material suitable for further use as a wood pulp or for further hydrolysis for the production of organic chemicals.
    Type: Grant
    Filed: January 11, 1988
    Date of Patent: May 2, 1989
    Assignee: Le Tourneau College
    Inventor: Leonard F. Burkart
  • Patent number: 4764596
    Abstract: Lignin is precipitated in high yields and at high rates from a black liquor produced by pulping wood at high temperatures and pressures with an aqueous lower aliphatic alcohol solvent. The lignin is precipitated by diluting the black liquor with water and an acid to form a solution with a pH of less than about 3, an alcohol content of less than about 30% by volume and a temperature of less than about 75.degree. C. The precipitated lignin, when subsequently dried, is in the form of a powder which requires little or no crushing to convert it into a fine uniform size suitable for use without further significant processing.
    Type: Grant
    Filed: December 11, 1986
    Date of Patent: August 16, 1988
    Assignee: Repap Technologies Inc.
    Inventors: Jairo H. Lora, Raphael Katzen, Malcolm Cronlund, Chih F. Wu
  • Patent number: 4728727
    Abstract: The present invention relates to modified lignosulfonate materials and the process for their preparation. These modified lignosulfonates result from the sulfonation of ultrafiltered lignosulfonates by reaction with sulfite-bisulfite salts. The removal of sugars and other low molecular weight impurities makes formation of these new modified lignosulfonates more complete. These derivative materials when reacted with metal salts such as chromium, ferrous, ferric, titanium, and zirconium produce oil well drilling fluid dispersant products with significantly improved performance and thermal properties.
    Type: Grant
    Filed: January 28, 1987
    Date of Patent: March 1, 1988
    Assignee: ITT Corporation
    Inventors: Marten Reintjes, Craig D. Marken
  • Patent number: 4493797
    Abstract: An autoclave extraction apparatus using supercritical fluid is used for supercritical fluid extraction of one or several compounds. The supercritical fluid containing the compound(s) may then be processed in a pressurized bed reactor under supercritical conditions. The bed being a fluidizable catalytic bed to carry out a catalytic reaction of the compound(s).The method is particularly applicable to recover valuable lignin and other extractable components from kraft black liquor.
    Type: Grant
    Filed: December 22, 1983
    Date of Patent: January 15, 1985
    Inventor: Michael M. Avedesian