With Phenolic Reactant Patents (Class 527/403)
  • Patent number: 11033867
    Abstract: A stable aqueous dispersion of solids in a liquid medium includes from 10 to 50 weight % (or 10 to 40 or 15 to 35 or 20 to 35 weight %), with respect to the total weight of the composition, of solids comprising a mixture of condensed and non-condensed lignin in an amount of at least 10 weight % (or 20 or 30 or 40 or 50 weight %) of the solids, and hemicellulose in an amount of at least 1 weight % (or 5 or 10 or 20 or 30 or 40 weight %) of the solids, in a substantially aqueous liquid medium.
    Type: Grant
    Filed: September 26, 2018
    Date of Patent: June 15, 2021
    Assignee: Sustainable Fiber Technologies, LLC
    Inventor: Mark Lewis
  • Patent number: 10894866
    Abstract: According to an example aspect of the present invention, there is provided a method of producing reactive lignin from an alkaline lignin containing stream, such as black liquor, e.g. kraft lignin, by using thermal treatment with temperatures between 200 and 250° C. for simultaneous activation (for example by demethylation and/or demethoxylation) and precipitation of the lignin.
    Type: Grant
    Filed: June 23, 2016
    Date of Patent: January 19, 2021
    Assignee: Teknologian tutkimuskeskus VTT Oy
    Inventors: Hanne Wikberg, Taina Ohra-Aho, Juha Leppävuori, Tiina Liitiä
  • Patent number: 9181405
    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: Grant
    Filed: January 13, 2012
    Date of Patent: November 10, 2015
    Assignee: General Electric Company
    Inventors: Hongchen Dong, Wenqing Peng, Larry Neil Lewis
  • Publication number: 20140039144
    Abstract: Compositions comprising lignin and low levels of undesirable impurities, such as compounds containing sulfur, nitrogen, or metals, are disclosed.
    Type: Application
    Filed: October 8, 2013
    Publication date: February 6, 2014
    Applicant: Renmatix, Inc.
    Inventors: Michel Adam Simard, Srinivas Kilambi, Kiran L. Kadam
  • Patent number: 8436120
    Abstract: A method of treating biomass feed by pyrolyzing it in the presence of superheated steam at a selected temperature for a sufficient time to produce at least one product stream.
    Type: Grant
    Filed: November 20, 2007
    Date of Patent: May 7, 2013
    Inventors: Jan Piskorz, Piotr Majerski
  • Publication number: 20120041146
    Abstract: The present invention provides methods to functionalize and solubilize WCNT with a phenolic polymer such as a lignin or a PF resin followed by in-situ integration of this functionalized CNT in the presence of formaldehyde and phenol and/or lignin to generate either CNT-reinforced phenol-formaldehyde polymer or CNT-reinforced lignin-phenol-formaldehyde polymer in either liquid or powder form suitable as an adhesive in the manufacture of a lignocellulosic composite material such as OSB and plywood.
    Type: Application
    Filed: July 27, 2011
    Publication date: February 16, 2012
    Applicants: NATIONAL RESEARCH COUNCIL OF CANADA, FPINNOVATIONS
    Inventors: Yaolin ZHANG, Xiang-Ming WANG, Martin FENG, Gilles BRUNETTE, Fuyong CHENG, Benoit SIMARD
  • Patent number: 7745559
    Abstract: An integrated circuit device includes: an internal circuit disposed on an inside area of the integrated circuit device; and at least one regulator circuit that generates a regulation voltage formed by stepping down a power supply voltage provided from outside, wherein an output terminal of the regulator circuit is connected to a first pad that is an external terminal of the integrated circuit device and a power supply line of the internal circuit, and the regulator circuit controls the state of the output terminal based on a plurality of control signals inputted respectively to a plurality of control terminals.
    Type: Grant
    Filed: August 29, 2007
    Date of Patent: June 29, 2010
    Assignee: Seiko Epson Corporation
    Inventor: Shinichiro Kobayashi
  • Publication number: 20080262182
    Abstract: 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: Application
    Filed: December 19, 2007
    Publication date: October 23, 2008
    Applicants: KABUSHIKI KAISHA MARUTO, MASAMITSU FUNAOKA
    Inventor: Masamitsu Funaoka
  • Patent number: 7276591
    Abstract: 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: Grant
    Filed: March 24, 2004
    Date of Patent: October 2, 2007
    Assignee: Fuji Carbon Co., Ltd.
    Inventors: Yaoguang Yao, Chuji Kitagawa, Motonobu Fujimori, Kaoru Fujimori
  • Patent number: 7064175
    Abstract: The adhesive system for use in binding lignocellulosic materials into a composite product, the adhesive system consisting essentially of a first part and one of (a) a second part; (b) a third part, and (c) both the second part and the third part; the first part being selected from the group consisting of powdered tannins, powdered modified tannins, and mixtures thereof; the second part being a powdered component reactive with the first part and selected from the group consisting of aldehyde polymers, phenolic resoles, modified phenolic resoles, and mixtures thereof; the third part being a liquid polymeric isocyanate, wherein: when the system consists essentially of the first part and (a) the second part, the weight ratio of the first part to the second part is from about 1:99 to about 65:35; when the system consists essentially of the first part and (b) the third part, the weight ratio of the first part to the third part is from about 1:99 to about 65:35; and when the system consists essentially of the fir
    Type: Grant
    Filed: April 26, 2002
    Date of Patent: June 20, 2006
    Assignee: Mitanic, Inc.
    Inventor: Edward M. Gres
  • Patent number: 6706808
    Abstract: The presently disclosed invention relates to a phenolic binder comprising a premix of a urea modified phenol-formaldehyde resole resin, a curing agent, and an additive selected from the group consisting of ammonium lignosulfonate, melamine and a melamine derivative. A method for reducing gaseous emissions in the manufacture of fibrous insulation materials is also disclosed.
    Type: Grant
    Filed: August 3, 1999
    Date of Patent: March 16, 2004
    Assignee: Owens Corning Fiberglas Technology, Inc.
    Inventors: Yadollah Delaviz, Susan Muench, Kathleen Bullock
  • Patent number: 6632912
    Abstract: Disclosed is a process for preparing phenol-formaldehyde thermoset resin that can contain up to 80% by weight a black liquor, preferably a sodium carbonate black liquor. Black liquor are by-products extracted from pulping process, which normally contain lignosulfonates, kraft lignin or sodium carbonate lignin as well as salts, depending on the process that is used. The use of such a black liquor permits to obtain a stable copolymerized phenol-formaldehyde thermoset resin. In the process, the black liquor is first mixed with phenol in the pressure of a base. Then, formaldehyde is added together with a base in two successive steps. The obtained thermoset resin has bonding properties that meet or exceed the CSA and ASTM requirements for the engineered forest products, such as wafer boards or oriented strand boards at pressing cycles of 16 mm per second or less.
    Type: Grant
    Filed: August 22, 2002
    Date of Patent: October 14, 2003
    Assignee: Silvachem, Inc.
    Inventor: Vikrant Sudan
  • Patent number: 6518387
    Abstract: The present invention relates to a soybean-based adhesive resin including a soybean flour and a cross-linking agent. The cross-linking agent is reacted with the functional groups in the soybean flour to form an adhesive resin. The present invention also relates to a method of making a soybean-based adhesive resin. This method involves providing an aqueous solution of soybean flour and adding a cross-linking agent to the solution under conditions effective to cross-link the soybean flour so that an adhesive resin is formed. Also disclosed is a composite product which includes particulate plant material and the soybean-based adhesive resin. The adhesive is prepared by reacting the cross-linking agent with the functional groups in the soybean flour. The present invention also relates to a method of making a composite product by providing particulate plant material and applying the soybean-based adhesive resin to the particulate plant material.
    Type: Grant
    Filed: September 4, 2001
    Date of Patent: February 11, 2003
    Assignee: Iowa State University Research Foundation, Inc.
    Inventors: Monlin Kuo, Deland J. Myers, Howard Heemstra, Daniel Curry, Daniel O. Adams, Douglas D. Stokke
  • Patent number: 6410674
    Abstract: The invention relates to an intermediate product for manufacturing polymers of lignin derivatives from the pulp industry, made by treating the lignin derivatives with phenol oxidizing enzymes in the presence of oxidation agents, characterized in that the lignin derivatives are (a) subjected to enzyme treatment for more than 3 hours in the presence of air, or (b) subjected to enzyme treatment for more than 10 minutes while air or oxygen is being passed through them, or (c) oxidized by treatment with chemical oxidation agents. The intermediate product is used in manufacturing polymers of lignin derivatives from the pulp industry, fiber-reinforced thermosetting composite materials from plant fibers, waterproof papers and cardboards, and thermosetting plastics from lignin derivatives.
    Type: Grant
    Filed: February 4, 2000
    Date of Patent: June 25, 2002
    Assignee: Stockhausen GmbH & Co. KG
    Inventors: Aloys Hüttermann, Andrzej Majcherczyk, Carsten Mai, Annette Braun-Lüllemann, Merle Fastenrath, Sonja Noetzold
  • Patent number: 6291558
    Abstract: This invention features a graft copolymer of lignosulfonates reacted with an unsaturated carbonyl compound and an aldehyde, in two separate reaction steps. The resin can be used as a substitute for a majority of pure urea formaldehyde resin in the manufacture of composite board products. The resin can also be introduced directly into the urea formaldehyde resin production process.
    Type: Grant
    Filed: July 2, 1999
    Date of Patent: September 18, 2001
    Assignee: Cellutech, LLC
    Inventors: Mikhail Raskin, Lazar O. Ioffe, Azariy Z. Pukis, Martin H. Wolf
  • Patent number: 6287708
    Abstract: An adhesive binder for bonding together lignocellulosic particles, fibers and flakes of vegetable origin to form particle boards, fiber boards, flake boards and similar wood-based products, comprising a solublized fraction obtained by enzymatic treatment of fibrous, lignocellulosic raw materials. The present binder can be obtained by treating fibrous lignocellulosic raw material with a hydrolytic enzyme in an aqueous medium, recovering the solubilized material of the enzymatic treatment, forming an aqueous suspension containing said material and an oxidase, and oxidizing said material in the presence of said oxidase by introducing oxygen-containing gas into the supension. This method thus produces an increased amount of a water-soluble fraction containing carbohydrates, extractives and lignin useful as an adhesive binder.
    Type: Grant
    Filed: November 9, 1999
    Date of Patent: September 11, 2001
    Assignee: Neste Chemicals Oy
    Inventors: Liisa Viikari, Anneli Hase, Pia Qvintus-Leino, Kirsi Kataja, Simo Tuominen, Lars Gädda
  • Patent number: 6280855
    Abstract: The invention relates to an intermediate product for the preparation of polymerizates from lignin derivatives obtained from the cellulose industry. The intermediate product is produced by treating the lignin derivatives with enzymes capable of oxidizing phenol in the presence of oxidizing agents. According to the invention the lignin derivatives are subjected to the enzymatic treatment for more than 3 hours in the presence of air, or they are subjected to an enzymatic treatment for more than 10 min, whereby air or oxygen is introduced. The lignin polymers obtained from the polymerization of lignin derivatives performed in the presence of active intermediate products are suited for use in the production of binding agents for wood materials.
    Type: Grant
    Filed: October 25, 1999
    Date of Patent: August 28, 2001
    Assignee: Neste Chemicals Oy
    Inventors: Liisa Viikari, Anneli Hase, Pia Qvintus-Leino, Marja-Leena Niku-Paavola
  • Publication number: 20010009955
    Abstract: The invention relates to an intermediate product for manufacturing polymers of lignin derivatives from the pulp industry, made by treating the lignin derivatives with phenol oxidizing enzymes in the presence of oxidation agents, characterized in that the lignin derivatives are (a) subjected to enzyme treatment for more than 3 hours in the presence of air, or (b) subjected to enzyme treatment for more than 10 minutes while air or oxygen is being passed through them, or (c) oxidized by treatment with chemical oxidation agents. The intermediate product is used in manufacturing polymers of lignin derivatives from the pulp industry, fiber-reinforced thermosetting composite materials from plant fibers, waterproof papers and cardboards, and thermosetting plastics from lignin derivatives.
    Type: Application
    Filed: February 4, 2000
    Publication date: July 26, 2001
    Inventors: ALOYS HUTTERMANN, ANDRZEJ MAJCHERCZYK, CARSTEN MAI, ANNETTE BRAUN-LULLEMANN, MERIE FASTENRATH, SONJA NOETZOLD
  • Patent number: 5866642
    Abstract: A low molecular weight lignin fraction having a pre-selected molecular weight range prepared from lignin solution by ultrafiltration. The invention also relates to phenol-formaldehyde resin modified by the lignin fraction, adhesive comprising the modified resin, and a method for producing the lignin fraction and the resin.
    Type: Grant
    Filed: May 19, 1993
    Date of Patent: February 2, 1999
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: Ted M. McVay, Gene F. Baxter, Frederick C. Dupre, Jr.
  • 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: 5591832
    Abstract: A benzylated lignocellulosic substance obtained through benzylation, wherein 46 to less than 97% of lignin-carbohydrate complex (LCC) contained in a wood raw material from which the substance is formed remains.
    Type: Grant
    Filed: November 21, 1994
    Date of Patent: January 7, 1997
    Assignee: Japan Chemical Engineering & Machinery Co., Ltd.
    Inventors: Tetsuo Koshijima, Nobuo Shiraishi, Tadashi Takahashi, Toshiharu Hiraoka, Masami Ueda
  • Patent number: 5407980
    Abstract: The present invention relates to an adhesive composition for manufacturing plywood for exterior application including:a) 121 parts by weight phenolic resin;b) 5 to 121 parts by weight isocyanate;c) 1 to 40 parts by weight tannin selected from the group consisting of pine, quebracho, mimosa, and combinations thereof;d) 1 to 15 parts by weight paraformaldehyde or formaldehyde solutions in water;e) 5 to 50 parts by weight of water; andf) an amount of filler comprising inorganic and/or organic materials for providing the composition with the desired viscosity.
    Type: Grant
    Filed: November 18, 1992
    Date of Patent: April 18, 1995
    Assignees: Diteco Ltda, Quimicos Coronel S.A.
    Inventors: Antonio Pizzi, Ernst Von Leyser, Cristian Westermeyer
  • Patent number: 5382608
    Abstract: A binder mixture containing lignin or lignins with reactive groups and phenol-novolac in a weight ratio of 95:5 to 50:50 useful for the production of non-woven fabrics and wood fiber materials.
    Type: Grant
    Filed: August 5, 1994
    Date of Patent: January 17, 1995
    Assignee: Rutgerswerke Aktiengesellschaft
    Inventors: Arno Gardzielia, Ken Kurple, Achim Hansen, Stephan Schroter, Willi Roll
  • Patent number: 5373070
    Abstract: A binder mixture containing lignin or lignins with reactive groups and phenol-novolac in a weight ratio of 95:5 to 50:50 useful for the production of non-woven fabrics and wood fiber materials.
    Type: Grant
    Filed: December 3, 1993
    Date of Patent: December 13, 1994
    Assignee: Rutgerswerke Aktiengesellschaft AG
    Inventors: Arno Gardziella, Ken Kurple, Achim Hansen, Stephan Schroter, Willi Roll
  • Patent number: 5260405
    Abstract: A binding agent for molding compositions and molded bodies produced by reacting a low molecular weight lignin from the Organosolv process with phenol in a weight ratio of 1:20 to 3:1 at 100.degree. to 180.degree. C., adjusting the pH to an acidic value and condensing the mixture with 0.2 to 0.9 moles of formaldehyde per mole of phenol at 60.degree. to 120.degree. C. to form the binding agent useful for producing curable molding compositions, high-temperature molding compositions, refractory products, textile fleeces and friction coatings as well as carbon materials.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: November 9, 1993
    Assignee: Rutgerswerke Aktiengesellschaft AG
    Inventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
  • Patent number: 5254639
    Abstract: A binding agent for molded bodies and molding compositions produced by prereacting a mixture of 5 to 60% by weight of lignin or a lignin fraction produced by the Organosolv process and 40 to 95% by weight of a phenol novolac resin and subjecting the latter to high shear forces in a kneader or extruder and optionally mixing the same with a curing agent useful in molding compositions and high temperature-stable molded products such as refractory products, friction coatings, textile fleeces and carbon or graphite materials.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: October 19, 1993
    Assignee: Rutgerswerke Aktiengesellschaft AG
    Inventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
  • Patent number: 5202403
    Abstract: A modified resole resin and an adhesive composition containing the resin wherein the resin is prepared by first reacting formaldehyde and a phenol at a mole ratio of formaldehyde to phenol of less than about 1.0 in the presence of alkaline in an amount sufficient to provide a mole ratio of said alkaline material to phenol between about 0.04 and 0.08 to form a precursor resin; reacting the precursor resin with lignin to form a lignin-modified phenol-formaldehyde precursor resin, and then reacting the lignin-modified phenol-formaldehyde precursor with additional formaldehyde sufficient to provide a cumulative formaldehyde to phenol mole ratio of between about 2.0 and about 3.0. The adhesive composition is useful in bonding wood chips, veneers and sheets of plywood.
    Type: Grant
    Filed: January 15, 1992
    Date of Patent: April 13, 1993
    Assignee: Georgia-Pacific Resins, Inc.
    Inventor: Glen A. Doering
  • 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: 5138007
    Abstract: The invention provides a series of methods for synthesizing a lignin graft copolymer or modifying the surface of a wood fiber or pulp and to provide a spectrum of reagents to use in the processes for preparing the lignin graft copolymer, grafted wood, grafted wood fiber, or grafted pulp and to provide a method of boosting or enhancing polymer molecular weights during polymerization reactions.
    Type: Grant
    Filed: February 14, 1990
    Date of Patent: August 11, 1992
    Inventor: John J. Meister
  • 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: 4988576
    Abstract: A wood preservative composition comprising a lignosulfonate copolymer and a metal salt or a combination of metal salts. The copolymer is a reaction product of lignosulfonate and acrylic monomers selected from a group of acrylic compounds of the general formula, RCH=CR.sup.1 COOH, where R is hydrogen, an alkyl or carboxyl group and R.sup.1 is hydrogen or an alkyl group, and the metal salt is a salt of sulfate, chloride, phosphate, or carbonate wherein the metal is selected from the group consisting of copper, zinc, mercury and lead. Alternatively, the composition may be a metal salt or a combination of metal salts of a lignosulfonate copolymer produced by base exchange of the corresponding calcium lignosulfonate copolymer with a metal salt or metal salts. The composition may be used, optionally, together with methylol phenol.
    Type: Grant
    Filed: December 13, 1989
    Date of Patent: January 29, 1991
    Assignee: Daishowa Chemicals Inc.
    Inventors: Stephen Y. Lin, Lori L. Bushar
  • Patent number: 4769434
    Abstract: A polymer material of the product of reaction of a grass plant lignin derivative comprising lignin polymer fragments recovered from black liquor obtained in the pulping of grass plant material and containing an average of more than 0.4 sites per phenyl propane unit of the polymer fragments reactive to base catalyzed substitution and condensation reactions, with an electrophilic compound which is capable of reacting twice at one side or at least once at each of two different sites.
    Type: Grant
    Filed: June 17, 1986
    Date of Patent: September 6, 1988
    Assignee: South African Inventions Development Corporation
    Inventors: Gerrit H. Van der Klashorst, Antonio Pizzi, Flora-Anne Cameron
  • Patent number: 4663367
    Abstract: Compositions and methods are used for reducing the permeability of high fluid permeability segments of underground strata, the compositions being injected into the high permeability segments in liquid form and there gelled to reduce the permeability of the segments. A first group of compositions has a pH of at least 4 and comprises a sulfited derivative of a tannin extract together with furfural, formaldehyde or a formaldehyde derivative. The second group of compositions comprises furfural and a gellable vegetable material which can be a tannin extract, a sulfited derivative of a tannin extract, a catechin, an alkaline extract of a coniferous bark or a lignin or sulfonated lignin derivative.
    Type: Grant
    Filed: February 19, 1985
    Date of Patent: May 5, 1987
    Assignee: The Borden Company Limited
    Inventors: Martin Navratil, Mark S. Mitchell, Mojmir Sovak
  • Patent number: 4642336
    Abstract: A method of producing ammonium salts of sulfomethylated lignins suited for use as dyestuff and coal-water slurry additives comprising of the steps of ionizing the phenol component of a lignin material by-product of the black liquor of a kraft paper-making process in an alkaline liquid medium, methylolating the lignin material, lowering the pH of the liquid medium to an acid pH to precipitate the methylolated lignin material, washing the precipitated lignin material with water to remove inorganic salts and residual reactants therefrom, and sulfonating the washed, purified methylolated lignin material with an ammonium salt of a sulphur-oxygen containing compound in a liquid medium.The washed, purified methylolated lignin material is preferably sulfonated at an acid pH level to minimize the production of electrolytes when the lignin is to be used for dyeing at low pH. Lignin products produced by the method, as well as dye and coal-water slurry compositions containing such products are also disclosed.
    Type: Grant
    Filed: December 10, 1984
    Date of Patent: February 10, 1987
    Assignee: Westvaco Corporation
    Inventor: Peter Dilling
  • Patent number: 4594384
    Abstract: The present invention relates to an adhesive composition for manufacturing glued laminated beams and wood constructions. One component of the adhesive composition is resorcinol-phenol resin. Resorcinol-phenol adhesives are as such known in the prior art. The main ingredients of these adhesives are resorcinol, formaldehyde and phenol. Among the drawbacks in the use and production of resorcinol-phenol adhesives are their high price and the fact that the raw materials are difficult to obtain. The purpose for employing the adhesive composition of the invention is to eliminate some of the difficulties connected with the availability of the raw materials, particularly resorcinol, and to help produce a new, more economical resorcinol-phenol based adhesive composition.
    Type: Grant
    Filed: December 21, 1984
    Date of Patent: June 10, 1986
    Assignee: Valtion Teknillinen Tutkimuskeskus
    Inventors: Harri Kilpelainen, Pentti Kankaanpaa
  • Patent number: 4537941
    Abstract: An improved modified phenol-formaldehyde resin, and a process for its preparation, which contains lignosulfonates is described. Typically, the lignosulfonates are in the form of black liquor. These resins are made by including with the phenol a small amount of potassium ferricyanide. Unlike the known processes utilizing black liquors and the like, this process appears to be far less susceptible to the inherent variability of these liquors. These resins can be easily converted into a solid by spray drying, and find use as adhesives, for example in board products.
    Type: Grant
    Filed: August 28, 1984
    Date of Patent: August 27, 1985
    Assignee: Reichhold Limited
    Inventors: Stamatis M. Kambanis, Antoine Berchem, Dennis Gregoire, Jaroslav Rybicky
  • Patent number: 4444562
    Abstract: Dispersants, especially well suited for use in thermosol dyeing processes, are produced by reacting methylol hydroxybenzene compounds with sulfonated lignin derivatives. The dispersants have high levels of heat stability and low staining characteristics, coupled with desirable dye reduction, foaming, milling and viscosity-reducing properties. Dyestuffs, dye pastes, and dye baths, as well as methods utilizing them, are provided.
    Type: Grant
    Filed: October 2, 1981
    Date of Patent: April 24, 1984
    Assignee: Reed Lignin, Inc.
    Inventor: Stephen Y. Lin
  • Patent number: 4423173
    Abstract: A method of manufacturing a lignosulfonate-phenol-formaldehyde resin includes heating a mixture of phenol, formaldehyde, lignosulfonate and alkali at a temperature of 60.degree. C. to 100.degree. C. and a pH of 8-13. The lignosulfonate comprises about 5 to about 80 percent of the total weight of phenol, formaldehyde and lignosulfonate and the lignosulfonate is mixed with said phenol and formaldehyde before substantial reaction between said phenol and said formaldehyde. Also disclosed are fibrous articles manufactured using this resin as a binder.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: December 27, 1983
    Assignee: Masonite Corporation
    Inventor: Eugene R. Janiga
  • Patent number: 4357454
    Abstract: A lignin product-containing binder and a process for its production are described.The lignin product consists of chlorolignin which has been treated with strong alkali (NaOH) for preferably 0.5-3 h. at 50.degree.-100.degree. C. and a pH of 10-13.5. The alkali-treated chlorolignin product can be used on its own as a binder component or, preferably, together with phenol-formaldehyde. The weight ratio phenol/lignin product is suitably from 4:1 to 1:4.
    Type: Grant
    Filed: August 20, 1981
    Date of Patent: November 2, 1982
    Assignee: Eka AB
    Inventors: Krister Holmberg, Jan-Allan Y. Johansson, Gerd E. Wallin
  • Patent number: 4320036
    Abstract: Ligno-novolak resins, either in the form of physical blends of lignin and novolak resins or as synthetically derived from the reaction of lignin, phenol and an aldehyde in the presence of an acidic catalyst, are provided. The resins, including the physical blends, are curable to thermoset, substantially completely cross-linked resins in which the lignin is interreacted and cross linked through the action of a curing agent such as hexamethylenetetramine. The resins are useful in the production of molding compounds that exhibit properties that are at least comparable to those of compounds derived from novolak resins. Moreover, excellent heat deflection temperatures and superior electrical properties are exhibited by such molding compounds.
    Type: Grant
    Filed: October 16, 1980
    Date of Patent: March 16, 1982
    Assignee: American Can Company
    Inventors: Riad H. Gobran, Akio Takahashi, Eugene P. Reilly
  • Patent number: RE32408
    Abstract: A method of manufacturing a lignosulfonate-phenol-formaldehyde resin includes heating a mixture of phenol, formaldehyde, lignosulfonate and alkali at a temperature of 60.degree. C. to 100.degree. C. and a pH of 8-13. The lignosulfonate comprises about 5 to about 80 percent of the total weight of phenol, formaldehyde and lignosulfonate and the lignosulfonate is mixed with said phenol and formaldehyde before substantial reaction between said phenol and said formaldehyde. Also disclosed are fibrous articles manufactured using this resin as a binder.
    Type: Grant
    Filed: November 26, 1985
    Date of Patent: April 28, 1987
    Assignee: Masonite Corporation
    Inventor: Eugene R. Janiga