From Lignin, Tannin, Or Derivative Reactant Patents (Class 527/400)
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Patent number: 6593460Abstract: 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: GrantFiled: October 12, 2000Date of Patent: July 15, 2003Assignee: Stockhausen GmbH & Co KGInventors: Aloys Hüttermann, Carsten Mai
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Patent number: 6517933Abstract: The invention is directed to a hybrid polymer material or system that combines naturally occurring building blocks with synthetic building blocks. The sets of naturally occurring and synthetic building blocks are mixed and joined on a molecular or nanoscopic level to give homogeneous or microphase-separated morphologies to the resulting mixed polymer system. These hybrid polymers combine the comfort attributes of natural materials with the robustness and design properties of synthetic materials.Type: GrantFiled: December 6, 2000Date of Patent: February 11, 2003Assignee: Nano-Tex, LLCInventors: David S. Soane, Matthew R. Linford, David A. Offord, Dan B. Millward, William Ware, Jr.
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Patent number: 6420533Abstract: This method will produce depolymerized lignins substantially free from sodium compounds. Black liquor supplied from a pulping process is utilized for providing a mixture of depolymerized lignins dispersed and dissolved in absolution containing sodium hydroxide. The mixture is then separated to form depolymerized lignins and a solution containing sodium hydroxide. Following separation, the depolymerized lignins are then extracted with water to produce an extractate containing water soluble sodium compounds. The extracted depolymerized lignins, containing sodium compounds, are then reacted with an acid to form sodium salts. The solution containing sodium salts is then separated from the extracted depolymerized lignins to produce substantially sodium free depolymerized lignins. The separated solution containing sodium hydroxide is combined with the extractate and the combination, subsequent to removal of water, is made available to reuse for recycle to depolymerize, disperse and dissolve additional lignins.Type: GrantFiled: August 4, 2000Date of Patent: July 16, 2002Inventor: Gene E. Lightner
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Patent number: 6339116Abstract: Biobased cross-linked compositions, methods of fabrication and structures, in particular biobased printed wiring boards using the compositions and methods of making the structures are described. Biobased materials such as lignin, crop oils, wood resins, tannins, and polysaccharides and combinations thereof are cross-linked, preferably using heat, a cross-linking agent, and an initiator. The materials fabricated have suitable properties for printed wiring boards which are made by impregnating a fiberglass or biobased cloth with an admixture of the biobased material, cross-linking agent and initiator which is processed by conventional methods to produce a printed wiring board.Type: GrantFiled: December 19, 1996Date of Patent: January 15, 2002Assignee: International Business Machines CorporationInventors: Ali Afzali-Ardakani, Jeffrey Donald Gelorme, Laura Louise Kosbar
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Patent number: 6291558Abstract: 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: GrantFiled: July 2, 1999Date of Patent: September 18, 2001Assignee: Cellutech, LLCInventors: Mikhail Raskin, Lazar O. Ioffe, Azariy Z. Pukis, Martin H. Wolf
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Patent number: 6287708Abstract: 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: GrantFiled: November 9, 1999Date of Patent: September 11, 2001Assignee: Neste Chemicals OyInventors: Liisa Viikari, Anneli Hase, Pia Qvintus-Leino, Kirsi Kataja, Simo Tuominen, Lars Gädda
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Patent number: 6280855Abstract: 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: GrantFiled: October 25, 1999Date of Patent: August 28, 2001Assignee: Neste Chemicals OyInventors: Liisa Viikari, Anneli Hase, Pia Qvintus-Leino, Marja-Leena Niku-Paavola
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Publication number: 20010009945Abstract: 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: ApplicationFiled: August 3, 1999Publication date: July 26, 2001Inventors: YADOLLAH DELAVIZ, SUSAN MUENCH, KATHLEEN BULLOCK
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Patent number: 6239198Abstract: 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: GrantFiled: September 1, 1999Date of Patent: May 29, 2001Assignee: Granit S.A.Inventors: Alfred Abächerli, Frank Doppenberg
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Patent number: 6072015Abstract: 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: GrantFiled: December 8, 1998Date of Patent: June 6, 2000Assignee: Genencor International, Inc.Inventors: Rob Bolle, Wolfgang Aehle
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Patent number: 5977287Abstract: There is provided a composition comprising tannin containing hydroxyl groups which has been (a) chemically modified by reaction of at least one of said hydroxyl groups with at least one member selected from the group consisting of an esterification agent (e.g. acetic anhydride), etherification agent (e.g. dichloromethane or quaternary organic amine such as N-(3-chloro-2-hydroxypropyl) trimethyl ammonium chloride) to form the corresponding ester, or ether, through said hydroxyl group, and (b) derivatized. The chemically modified tannin is derivatized by reaction with aldehyhde (e.g. formaldehyde), or aldehyde and at least one member selected from the group consisting of ammonia and organic amine containing at least one primary or secondary nitrogen (e.g. cyclohexyl amine); said derivatized tannin being water soluble or dispersable at a pH below 7 and water insoluble at a pH above 7.Type: GrantFiled: July 16, 1998Date of Patent: November 2, 1999Assignee: BetzDearborn Inc.Inventors: David Brian Mitchell, Ralph Lemmel Minnis, Thomas Peter Curran, Steven M Deboo, John Arthur Kelly, Rashmi Patwardhan, Wun Ten Tai
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Patent number: 5916991Abstract: Tannin containing polymers, their method of production and methods of using as water treatment agents are disclosed. The tannin containing polymers comprise copolymers of tannin and a cationic monomer. Another embodiment comprises tannin containing polymers of tannin, cationic monomer and at least one monomer selected from the group consisting of an anionic monomer and a nonionic monomer.Type: GrantFiled: July 8, 1997Date of Patent: June 29, 1999Assignee: BetzDearborn Inc.Inventors: Jen-Chi Chen, Fu Chen, Gerald C. Walterick, Jr.
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Patent number: 5852069Abstract: 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: GrantFiled: October 2, 1997Date of Patent: December 22, 1998Inventors: John J. Meister, Meng-Jiu Chen
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Patent number: 5807952Abstract: A process for the production of low molecular weight phenolic compounds from lignins through the pyrolysis of the lignins in the presence of a strong base. In a preferred embodiment, potassium hydroxide is present in an amount of from about 0.1% to about 5% by weight, the pyrolysis temperature is from about 400.degree. C. to about 600.degree. C. at atmospheric pressure, and the time period for substantial completion of the reaction is from about 1-3 minutes. Examples of low molecular weight phenolic compounds produced include methoxyphenols, non-methoxylated phenols, and mixtures thereof.Type: GrantFiled: May 2, 1996Date of Patent: September 15, 1998Assignee: Midwest Research InstituteInventor: Foster A. Agblevor
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Patent number: 5763557Abstract: The invention relates to the chemical bonding of a polymer/or polymers onto non-metallic substrates such as cellophane by ultrasonic techniques. The cellophane film is preactivated by contacting with silver nitrate solution followed by treatment with potassium hydroxide solution whereby particles of silver and silver oxide are uniformly distributed, in situ, over the surface of cellophane film. The pretreated cellophane film when contacted with grafting solution, that contains monomers, prepolymers, catalyst, graft initiator and other ingredients of the composition, which is being agitated with ultrasonic energy results in polymerization of monomer/prepolymer onto the surface of the cellophane film.Type: GrantFiled: September 24, 1996Date of Patent: June 9, 1998Assignee: Polymer Research Corp. of AmericaInventors: Mohan L. Sanduja, Carl Horowitz, Paul Thottathil
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Patent number: 5741875Abstract: 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: GrantFiled: March 8, 1995Date of Patent: April 21, 1998Inventors: John J. Meister, Meng-Jiu Chen
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Patent number: 5719224Abstract: A method and composition for detackifying or coagulating and flocculating waterborne and mixed waterborne/solventborne paints in paint spray booth water. Aluminum chlorohydrate and a tannin containing polymer, preferably in an aqueous solution, are added to the paint spray booth water to detackify or coagulate and flocculate the paints.Type: GrantFiled: October 25, 1996Date of Patent: February 17, 1998Assignee: BetzDearborn Inc.Inventors: Howard B. Agree, Jen-Chi Chen, Robert A. Iezzi
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Patent number: 5684109Abstract: Tannin containing polymers, their method of production and methods of using as water treatment agents are disclosed. The tannin containing polymers comprise copolymers of tannin and a cationic monomer. Another embodiment comprises tannin containing polymers of tannin, cationic monomer and at least one monomer selected from the group consisting of an anionic monomer and a nonionic monomer.Type: GrantFiled: May 20, 1994Date of Patent: November 4, 1997Assignee: BetzDearborn Inc.Inventors: Jen-Chi Chen, Fu Chen, Gerald C. Walterick, Jr.
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Patent number: 5665573Abstract: The present invention relates to a method of enzymatic polymerization and/or modification of lignin or lignin containing materials. The invention also relates to the use of this method in the manufacture of wood composites or wood laminates.Type: GrantFiled: December 1, 1994Date of Patent: September 9, 1997Assignee: Novo Nordisk A/SInventor: Birgitte Yde
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Patent number: 5656708Abstract: A process for making a water-insoluble, graft copolymer of lignite-(ethene or substituted ethene monomer) having a central lignite network and at least one grafted side chain, R, having "m" repeating units of (1-phenylethylene), 1-methyl-1-(1-oxo-2-oxypropyl)ethylene, a polymerized 2-methyl-3-oxo-4-oxybut-1-ene-(p-ethoxy-(3*p+3)-ol), or any other substituted ethene monomer which has a dipole moment of less than 1.2 or a water solubility of less than 5 g/100 g water at 30.degree. C. The ethene monomer forms the sidechain by free radical polymerization and, in the sidechain, m and p vary from 1 to 300,000 such that the central lignite network has a molecular weight of about 1,000 to 1,500,000; the total number of random units in a grafted side chain is in the range of 1 to 300,000 units; and the total number of sidechains attached to lignite, x, is in the range of 1 to 500; such that the total copolymer molecular weight is in the range of 1,500 to 30,000,000.Type: GrantFiled: June 5, 1995Date of Patent: August 12, 1997Inventor: John J. Meister
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Patent number: 5648116Abstract: Methods for suppressing the dissemination of dust emissions from dust producing materials are disclosed. Fugitive dust emissions are suppressed by applying aqueous solutions of a copolymer of tannin and a cationic monomer to the dust producing materials.Type: GrantFiled: January 17, 1996Date of Patent: July 15, 1997Assignee: BetzDearborn Inc.Inventors: Donald C. Roe, Jen-Chi Chen
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Patent number: 5614103Abstract: A method and composition for detackifying or coagulating and flocculating waterborne and mixed waterborne/solventborne paints in paint spray booth water. Aluminum chlorohydrate and a tannin containing polymer, preferably in an aqueous solution, are added to the paint spray booth water to detackify or coagulate and flocculate the paints.Type: GrantFiled: December 13, 1994Date of Patent: March 25, 1997Assignee: BetzDearborn, Inc.Inventors: Howard B. Agree, Jen-Chi Chen, Robert A. Iezzi
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Patent number: 5608040Abstract: Polymers containing lignin and organic compounds are produced by polymerizing the lignin with organic compounds containing at least 3 carbon atoms as well as oxygen, nitrogen and/or multiple-linkage functions in the presence of radically oxidizing enzymes and of oxidation products constituting their substrate.Type: GrantFiled: July 6, 1995Date of Patent: March 4, 1997Assignee: Aloys H uttermannInventors: Aloys H uttermann, Oleg Milstein
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Patent number: 5591832Abstract: 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: GrantFiled: November 21, 1994Date of Patent: January 7, 1997Assignee: Japan Chemical Engineering & Machinery Co., Ltd.Inventors: Tetsuo Koshijima, Nobuo Shiraishi, Tadashi Takahashi, Toshiharu Hiraoka, Masami Ueda
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Patent number: 5502088Abstract: This invention refers to a wood substitute with lignocellulosic and mineral material particles which are molded in sheet, e.g. plates and/or panels in different thicknesses or forms in stencil at choice, using in principal natural and artificial, and vegetal cellulosic material components, e.g. dried leaves, sawdust, rotten wood particles splinters, paperwastes, roots and mineral materials as limestone from sulphates type carbonates or calcium oxides, with synthetic binders from different chemical structures, with or without dyes, in these proportions: 35-60 by weight lignocellulosic components particles, 5-35 by weight limestone types, 5-30 by weight synthetic binders from different harmless chemical structures, with or without synthetic dyes from varied chemical structures and with or without requested additions.Type: GrantFiled: June 6, 1994Date of Patent: March 26, 1996Inventor: Andrei Hododi
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Patent number: 5484895Abstract: A graft copolymer of a vascular plant having a biologically produced part that is the plant or a component thereof and at least one sidechain, Sc, having randomly repeat unit, R.sub.ru, wherein R.sub.ru are formed by the polymerization of at least one substituted ethene polymerable by free radical polymerization. The sidechain repeat unit, R.sup.ru, has the structure ##STR1## such that the side groups, R.sub.i where i=1 to 4, on the sidechain are selected from the group of alkanes, alkenes, amides, alcohols, alkoxides, aromatics, cycloalkanes, esters, halogens, hydrogen, phenols, and nitrile groups and such groups further substituted with one or more groups. The side groups on the sidechain may vary from one repeat unit to another. The number of sidechains on the woody plant fragment can vary from 1 to 500 and the number of repeat units in each sidechain can vary from 1 to 500,000.Type: GrantFiled: April 8, 1993Date of Patent: January 16, 1996Inventors: John J. Meister, Meng-Jiu Chen
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Patent number: 5424382Abstract: 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: GrantFiled: June 21, 1993Date of Patent: June 13, 1995Inventors: John J. Meister, Meng-Jiu Chen
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Patent number: 5417888Abstract: A method for producing a relatively low viscosity tannin extract from bark and/or wood and suitable for use in formaldehyde-condensation adhesives comprises providing tannin extract obtained from bark and/or wood, separating from the tannin extract the high molecular weight material, subjecting the high molecular weight material to treatment with one or more sulphite compounds to reduce the molecular weight and recombining the sulphited material with the tannin extract. The tannin extract may be recovered by subjecting bark and/or wood to a first stage hot aqueous tannin extraction process, thereby obtaining a first stage tannin extract, subjecting the extracted bark and/or wood to a second stage hot aqueous extraction process at a higher pH than the first stage, thereby obtaining a second stage tannin extract, and optionally recombining the first and second stage tannin extracts.Type: GrantFiled: January 24, 1994Date of Patent: May 23, 1995Assignee: Commonwealth Scientific and Industrial ResearchInventors: Peter J. Collins, Yoshikazu Yazaki
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Patent number: 5371194Abstract: A multi-purpose resin synthesized from a mixture of a protein and a carbohydrate by ammoniation instead of hydrolysis is described. Any primary product of photosynthesis (glucose, starch or lignocellulose) is qualified for use as the carbohydrate component of the resin, which is an expedient, low-cost and benign substitute for conventional thermosetting resins in the manufacture of numerous industrial products.Type: GrantFiled: October 21, 1992Date of Patent: December 6, 1994Inventor: Arthur Ferretti
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Patent number: 5331088Abstract: A process for making a water-insoluble, graft copolymer of lignite-(ethene or substituted ethene monomer) having a central lignite network and at least one grafted side chain, R, having "m" repeating units of (1-phenylethylene), 1-methyl-1-(1-oxo-2-oxypropyl)ethylene, a polymerized 2-methyl-3-oxo-4-oxybut-1-ene-(p-ethoxy-(3*p+3)-ol, or any other substituted ethene monomer which has a dipole moment of less than 1.2 or a water solubility of less than 5 g/100 g water at 30.degree. C. The ethene monomer forms the sidechain by free radical polymerization and, in the sidechain, m and p vary from 1 to 300,000 such that the central lignite network has a molecular weight of about 1,000 to 1,500,000; the total number of random units in a grafted side chain is in the range of 1 to 300,000 units; and the total number of sidechains attached to lignite, x, is in the range of 1 to 500; such that the total copolymer molecular weight is in the range of 1,500 to 30,000,000.Type: GrantFiled: November 16, 1992Date of Patent: July 19, 1994Inventor: John J. Meister
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Patent number: 5194552Abstract: A soluble, solid, or crosslinked graft copolymer of lignin-(2-propenamide)-(2-methyl-3-oxo-4-oxybut-1-ene-(p-ethoxy-(3*p+3)-ol ) having a central lignin network and at least one grafted side chain, R, having randomly repeating units of the formula: ##STR1## such that the central lignin network has a molecular weight of about 1,000 to 150,000; the number of ethoxyl repeat units, p, in the polyol repeat unit is between 1 and 300,000; and the total number of random units in the grafted side chain, n+m, or chains, x*(n+m), is in the range of 1 to 300,000 units, such that the total copolymer molecular weight is in the range of 1,000 to 300,000,000.The copolymers of the present invention are useful as 1) thickeners for water and aqueous solutions or 2) plastics and elastomers.Type: GrantFiled: March 27, 1992Date of Patent: March 16, 1993Inventors: John J. Meister, Amit Lathia, Fu-Fong Chang
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Patent number: 5177169Abstract: 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: GrantFiled: May 29, 1991Date of Patent: January 5, 1993Assignee: Colorado State University Research FoundationInventor: Herbert A. Schroeder
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Patent number: 5147964Abstract: A process for forming an oil well cement composition comprising: mixing cement and a vinyl grafted wattle tannin fluid loss additive, the vinyl grafted wattle tannin comprising a wattle tannin grafted with at least one vinyl monomer selected from the group consisting of: 2-acrylamido-2-methylpropanesulfonic acid and acrylamide, wherein the wattle tannin is present in an amount of between about 0.05 to about 14 weight percent based on actives, the 2-acrylamido-2-methylpropanesulfonic acid is present in an amount of between about 68 to about 99.95 percent, and acrylamide is present in an amount of between about 0 to about 18 percent, to form a cement blend; and mixing the cement blend with water.Type: GrantFiled: April 23, 1991Date of Patent: September 15, 1992Assignee: Nalco Chemical CompanyInventors: David A. Huddleston, Robert K. Gabel, Charles D. Williamson
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Patent number: 5138007Abstract: 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: GrantFiled: February 14, 1990Date of Patent: August 11, 1992Inventor: John J. Meister
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Patent number: 5134215Abstract: A process for forming an oil well cement composition comprising: mixing cement and a vinyl grafted wattle tannin fluid loss additive, the vinyl grafted wattle tannin comprising a wattle tannin grafted with at least one vinyl monomer selected from the group consisting of: 2-acrylamido-2-methylpropanesulfonic acid and acrylamide, wherein the wattel tannin is present in an amount of between about 2 to about 14 weight percent based on actives, the 2-acrylamido-2-methylpropanesulfonic acid is present in an amount of between about 84 to about 98 percent, and acrylamide is present in an amount of between about 0 to about 4 percent, to form a cement blend; and mixing the cement blend with water.Type: GrantFiled: October 15, 1990Date of Patent: July 28, 1992Assignee: Nalco Chemical CompanyInventors: David A. Huddleston, Robert K. Gabel, Charles D. Williamson
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Patent number: 5121801Abstract: A soluble or crosslinked graft copolymer of lignin-(2-propenamide)-(2-methyl-3-oxo-4-oxyhex-1-ene-6-ol) having a central lignin network and at least one grafted side chain, R, having randomly repeating units of the formula: ##STR1## such that the central lignin network has a molecular weight of about 1,000 to 150,000 and the total number of randomly repeating units in the grafted side chain or chains is in the range of 1 to 300,000, such that the total copolymer molecular weight is in the range of 1,000 to 30,000,000 for use as thickeners for water and aqueous solutions and may be advantageously used in the recovery of oil from subterranean wells, in the preparation and use of drilling fluid compositions, or in plastics and elastomers.Type: GrantFiled: September 18, 1989Date of Patent: June 16, 1992Inventor: John J. Meister
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Patent number: 5116904Abstract: A soluble, solid, or crosslinked graft copolymer of lignin-(2-propenamide)-(2-methyl-3-oxo-4-oxybut-1-ene-(p-ethoxy-(3*p +3)-ol) having a central lignin network and at least one grafted side chain, R, having randomly repeating units of the formula: ##STR1## such that the central lignin network has a molecular weight of about 1,000 to 150,000; the number of ethoxyl repeat units, p, in the polyol repeat unit is between 1 and 300,000; and the total number of random units in the grafted side chain, n+m, or chains, x*(n+m), is in the range of 1 to 300,000 units, such that the total copolymer molecular weight is in the range of 1,000 to 300,000,000.The copolymers of the present invention are useful as 1) thickeners for water and aqueous solutions or 2) plastics and elastomers.Type: GrantFiled: October 22, 1990Date of Patent: May 26, 1992Inventors: John J. Meister, Amit Lathia, Fu-Fong Chang
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Patent number: 5102992Abstract: A method of producing prepolymeric materials from lignin is disclosed. The method uses lignin which has been hydroxyalkyl modified, such that the lignin is substantially non-phenolic and solvent soluble and/or liquid. The modified lignin is reacted with materials which yield prepolymers which may be polymerized according to known methods to produce useful polymers.Type: GrantFiled: August 20, 1990Date of Patent: April 7, 1992Assignees: Center for Innovative Technology, Virginia Polytechnic Institute and State UniversityInventors: Wolfgang G. Glasser, Willer De Oliveira, Stephen S. Kelley, Li S. Nieh
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Patent number: 5075402Abstract: A non-toxic stable lignosulfonate-urea-formaldehyde composition. The composition is particularly useful as a binder for animal feeds. A method of making the composition is also disclosed.Type: GrantFiled: November 21, 1990Date of Patent: December 24, 1991Assignee: Ligno Tech. U.S.A.Inventors: Linda G. Schmitt, John W. Hollis, Jr.
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Patent number: 5049612Abstract: A new depressant for use in enhanced separation of polymetallic sulphides is described. The depressant agent is used in conjunction with conventional collector agents and forthing agents in the flotation separation of copper, nickel, lead, zinc sulphides by depressing iron sulphides such as pyrrhotite, pyrite and marcasite in the tailing. The depressant consists of a cross-linked starch chemically combined with a polyacrylate and sugar free lignin sulphonate.Type: GrantFiled: January 3, 1989Date of Patent: September 17, 1991Assignee: Falconbridge LimitedInventors: Srdjan Bulatovic, Tim M. Jessup, James F. Jackson
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Patent number: 5037931Abstract: A soluble or crosslinked graft copolymer of lignin-(2-propenamide)-(2-methyl-3-oxo-4-oxyhex-1-ene-6-ol) having a central lignin network and at least one grafted side chain, R, having randomly repeating units of the formula: ##STR1## such that the central lignin network has a molecular weight of about 1,000 to 150,000 and the total number of randomly repeating units in the grafted side chain or chains is in the range of 1 to 300,000, such that the total copolymer molecular weight is in the range of 1,000 to 30,000,000 for use as thickeners for water and aqueous solutions and may be advantageously used in the recovery of oil from subterranean wells, in the preparation and use of drilling fluid compositions, or in plastics and elastomers.Type: GrantFiled: November 8, 1990Date of Patent: August 6, 1991Inventor: John J. Meister
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Patent number: 5026808Abstract: 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: GrantFiled: April 3, 1989Date of Patent: June 25, 1991Assignee: Colorado State University Research FoundationInventor: Herbert A. Schroeder
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Patent number: 5021531Abstract: 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: GrantFiled: February 20, 1990Date of Patent: June 4, 1991Assignee: Colorado State University Research FoundationInventor: Herbert A. Schroeder
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Patent number: 4988576Abstract: 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: GrantFiled: December 13, 1989Date of Patent: January 29, 1991Assignee: Daishowa Chemicals Inc.Inventors: Stephen Y. Lin, Lori L. Bushar
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Patent number: 4977227Abstract: This invention provides a cement dispersant of a lignosulfonic acid graft copolymer, obtained by a redox free radical reaction of lignosulfonic acid or its salts with one or more acrylic or vinylic monomers containing functional groups, in an aqueous solution in the presence of a radical initiator, e.g, redox catalyst. The lignosulfonic acid graft copolymer has a molecular weight distribution of from 5.times.10.sup.2 to 5.times.10.sup.6.Type: GrantFiled: November 28, 1988Date of Patent: December 11, 1990Assignee: Sandoz Ltd.Inventors: Shin'ichi Negami, Hiroshi Nomachi, Toru Nemoto, Yoshio Tanaka, Akira Ohta
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Patent number: 4952329Abstract: A new depressant composition is provided for the enhanced separation into separate value metal concentrates of copper, nickel, zinc, lead present in polymetallic and massive sulphide ores.The depressant is added in an aqueous solution prepared by dissolving first a mixture of quebrachio and dextrin, or quebracho and guar gum. To the solution of modified quebracho a water soluble salt of lignin sulphonate is added. The aqueous polymer of modified quebracho lignin sulphonate is further mixed with one or more of the following inorganic reagents: water soluble cyanide, metal sulphates and water soluble sulphites. The resulting depressant is added together with conventional flotation reagents in conventional mineral separation stages as required.Type: GrantFiled: August 29, 1989Date of Patent: August 28, 1990Assignee: Falconbridge LimitedInventors: Srdjan Bulatovic, Robert S. Salter
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Patent number: 4940764Abstract: A water-soluble graft copolymer of lignin-(2-propenamide)-(2-methyl-N7,N7-dimethyl-7-ammonium-3-oxo-4-oxyoct- 1-ene chloride or methylsulfate) having a central lignin network and at least one grafted side chain, R, having randomly repeating units of the formula: ##STR1## such that the central lignin network has a molecular weight of about 1,000 to 150,000 and the total number of randomly repeating units in the grafted side chain or chains is in the range of 50 to 300,000 such that the total copolymer molecular weight is in the range of 15,000 to 30,000,000.Type: GrantFiled: December 19, 1988Date of Patent: July 10, 1990Inventor: John J. Meister
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Patent number: 4938803Abstract: A vinyl grafted lignite fluid loss additive comprising a lignite grafted with at least one vinyl monomer selected from the group consisting of: dimethylaminopropyl methacrylamide, methacrylamido propyltrimethyl ammonium chloride, N-vinylformamide, N-vinylacetamide, diallyl dimethyl ammonium chloride, and diallylamine. The vinyl monomer may also be blended with at least one co-monomer. Preferred co-monomers are: 2-acrylamido-2-methylpropanesulfonic acid, dimethylacrylamide, acrylamide, vinylpyrrolidone, vinylacetate, acrylonitrile, dimethylaminoethyl methacrylate, styrenesulfonate, vinylsulfonate, dimethylaminoethyl methacrylate methyl chloride quaternary, acrylic acid and its salts.Type: GrantFiled: July 5, 1989Date of Patent: July 3, 1990Assignee: Nalco Chemical CompanyInventors: David A. Huddleston, Charles D. Williamson
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Patent number: 4931527Abstract: A water-soluble graft copolymer of lignin-(2-propenamide)-(4n,4n-dimethyl-4-ammoniumhept-1,6-diene chloride) having a central lignin network and at least one grafted side chain, R, having randomly repeating units of the formulas: ##STR1## such that the central lignin network has a molecular weight of about 1,000 to 150,000 and the total number of randomly repeating units in the grafted side chain or chains is in the range of 5 to 300,000 such that the total copolymer molecular weight is in the range of 1,000 to 30,000,000.Type: GrantFiled: December 19, 1988Date of Patent: June 5, 1990Inventor: John J. Meister
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Patent number: 4891415Abstract: A graft copolymer of lignin and vinylic monomer is produced by a continuous process wherein the vinylic monomer and a suitable initiator compound are continuously, but separately, fed to a solution of the lignin. The monomer is selected from a group consisting of the general formula RCH.dbd.CHR'R" where R and R' are H, or alkyl group, and R" is --COOH, --CN or --CONH.sub.2 and the initiator is hydrogen peroxide, organic peroxides or persulfates.Type: GrantFiled: January 23, 1989Date of Patent: January 2, 1990Assignee: Daishowa Chemicals Inc.Inventors: Stephen Y. Lin, Lori L. Bushar