Abstract: Water based lignoepoxy resins, and methods for their preparation and use are provided. Methods of making lignoepoxy resins without the use of volatile organic compounds are also provided.

Abstract: This invention discloses a high-performance lignin-based water reducer with high degree of sulfonation and high molecular weight and its preparation method. This water reducer exhibits an excellent water-reducing performance, its water-reducing rate of this lignin-based water reducer reaches 25% at a dosage of 0.70 wt %, which is higher than that of the naphthalene-based water reducer and the sulfonated lignin water reducer prepared by oxidation and sulfonation of alkali lignin, and 28-days compressive strength ratio of the concrete with this water reducer to the concrete without this water reducer is up to 150:100. Furthermore, the water reducer of present invention will not be crystallized in winter, and the concrete iron won't be corroded. The water reducer of the present invention makes the concretes having a low bleeding rate, excellent properties of workability, anti-freeze and anti-carbonization.

Abstract: Methods for converting waste streams from the wood pulping industry to high-value surfactants are described. For example, isolated lignin and lignosulfonate or waste streams containing lignin and lignosulfonate can be directly converted to surfactants, or they can be first converted to methylol derivatives and treated with further reagents to produce surfactants.

Abstract: This invention discloses a high-performance lignin-based water reducer with high degree of sulfonation and high molecular weight and its preparation method. This water reducer exhibits an excellent water-reducing performance, its water-reducing rate of this lignin-based water reducer reaches 25% at a dosage of 0.70 wt %, which is higher than that of the naphthalene-based water reducer and the sulfonated lignin water reducer prepared by oxidation and sulfonation of alkali lignin, and 28-days compressive strength ratio of the concrete with this water reducer to the concrete without this water reducer is up to 150:100. Furthermore, the water reducer of present invention will not be crystallized in winter, and the concrete iron won't be corroded. The water reducer of the present invention makes the concretes having a low bleeding rate, excellent properties of workability, anti-freeze and anti-carbonization.

Abstract: The present invention provides for novel compositions and methods for recycling or recovering ionic liquid used in IL pretreated cellulose and/or lignocellulosic biomass (LBM).

Abstract: Water based lignoepoxy resins, and methods for their preparation and use are provided. Methods of making lignoepoxy resins without the use of volatile organic compounds are also provided.

Abstract: The present disclosure relates to reactive modified lignin, methods of preparing such modified lignin, and materials, such as polymer systems, incorporating the modified lignin. More specifically, the lignin can be modified by selectively masking reactive functional groups such that the material has a modulated reactivity and is thus better suited for incorporation into and/or formation of further materials, such as carbon fibers.

Abstract: A friction material containing, as a binder, a lignin-phenol resin having a weight average molecular weight of 5,000 or less or a cardanol-modified lignin-phenol resin having a weight average molecular weight of 5,000 or less. The friction material is produced by a method including: reacting a lignin having a weight average molecular weight of 5,000 or less, a phenol, an aldehyde, and optionally a cardanol, in the presence of an acid catalyst.

Abstract: Methods for converting waste streams from the wood pulping industry to high-value concrete admixtures are described. For example, isolated lignin and lingnosulfonate or waste streams containing lignin and lingnosulfonate can be directly converted to the concrete admixtures, or they may be first converted to their methylol derivatives and treated with further reagents to produce the concrete admixtures.

Abstract: Methods for converting waste streams from the wood pulping industry to high-value fertilizers are described. For example, isolated lignin and lignosulfonate or waste streams containing lignin and lignosulfonate can be converted to methylol derivatives and treated with further reagents to produce controlled release fertilizers, hydrogel fertilizers, and soil stabilizers.

Abstract: A cationic electrodepositable coating composition is disclosed. The present invention in directed to a cationic electrodepositable coating composition comprising a lignin-containing cationic salt resin, that comprises (A) the reaction product of: lignin, an amine, and a carbonyl compound; (B) the reaction product of lignin, epichlorohydrin, and an amine; or (C) combinations thereof.

Abstract: Disclosed is a flame retardant agent, including a nitrogen-based lignin formed by reacting 1 part by weight of lignin, 0.8 to 2.4 parts by weight of a nitrogen-containing compound, and 0.3 to 0.9 parts by weight of an aldehyde under an alkaline condition. The flame retardant agent can be added to thermoplastic or thermosetting resins to form flame retardant materials.

Abstract: The present invention relates to a crosslinked lignin comprising a lignin structure having methylene or ethylene linking groups therein crosslinking between phenyl ring carbon atoms, wherein said crosslinked lignin is crosslinked to an extent that it has a number-average molecular weight of at least 10,000 g/mol, is melt-processible, and has either a glass transition temperature of at least 100° C., or is substantially soluble in a polar organic solvent or aqueous alkaline solution. Thermoplastic copolymers containing the crosslinked lignin are also described. Methods for producing the crosslinked lignin and thermoplastic copolymers are also described.

Abstract: This invention discloses a high-performance lignin-based water reducer with high degree of sulfonation and high molecular weight and its preparation method. This water reducer exhibits an excellent water-reducing performance, its water-reducing rate of this lignin-based water reducer reaches 25% at a dosage of 0.70 wt %, which is higher than that of the naphthalene-based water reducer and the sulfonated lignin water reducer prepared by oxidation and sulfonation of alkali lignin, and 28-days compressive strength ratio of the concrete with this water reducer to the concrete without this water reducer is up to 150:100. Furthermore, the water reducer of present invention will not be crystallized in winter, and the concrete iron won't be corroded. The water reducer of the present invention makes the concretes having a low bleeding rate, excellent properties of workability, anti-freeze and anti-carbonization.

Abstract: Disclosed is a flame retardant agent, including a nitrogen-based lignin formed by reacting 1 part by weight of lignin, 0.8 to 2.4 parts by weight of a nitrogen-containing compound, and 0.3 to 0.9 parts by weight of an aldehyde under an alkaline condition. The flame retardant agent can be added to thermoplastic or thermosetting resins to form flame retardant materials.

Abstract: Delignification of biomass consisting of lignin containing plant is done by utilizing an amino compound in and aqueous solution at ambient temperature up to 150 degree C. to produce and aqueous solution of amino salt of lignin and an amino-lignin-cellulose which is not soluble in water. The aqueous solution of amino salt of lignin is then filtered off of the amino-lignin-cellulose. The aqueous solution of amino salt of lignin or the amino salt of lignin with the amino-lignin-cellulose may be reacted with an aldehyde to produce an amino-lignin-aldehyde resin or an amino-lignin-cellulose aldehyde resin which may be of the thermoplastic or thermosetting type. The thermoplastic resins are fire resistant, hard, strong, not water soluble and may be used to make exterior fiberboard, OAS boards, plywood, molded products, etc. These urea salts of lignin may also be utilized as long acting fertilizer, to produce plastics and other products.

Abstract: A cationic electrodepositable coating composition is disclosed.

Abstract: The present invention disclosed a concrete water reducer by grafting of lignosulfonate with carbonyl aliphatics and its preparation method. A technical solution of the method is as follows: compound proportioning of the concrete water reducer (weight) is: carbonyl group aliphatics:lignosulfonate=1:(0.75-1). The said concrete water reducer by grafting of lignosulfonate with carbonyl aliphatics is prepared through following process steps: controlling the temperature of aliphatics water reducer at 95-100° C.; dropping lignosulfonate into said aliphatics water reducer; conducting graft copolymerization reaction at 95° C.-100° C. for 2-5 h and obtaining lignosulfonate modified and grafted aliphatics concrete water reducer. The method of present application is simple, low cost and friendly to environment. The water reducer has good water reducing effect and can reduce colour aberration of concrete and thus be applied broadly.

Abstract: Delignification of biomass consisting of lignin containing plant is done by utilizing an amino compound in and aqueous solution at ambient temperature up to 150 degree C. to produce and aqueous solution of amino salt of lignin and an amino-lignin-cellulose which is not soluble in water. The aqueous solution of amino salt of lignin is then filtered off of the amino-lignin-cellulose. The aqueous solution of amino salt of lignin or the amino salt of lignin with the amino-lignin-cellulose may be reacted with an aldehyde to produce an amino-lignin-aldehyde resin or an amino-lignin-cellulose aldehyde resin which may be of the thermoplastic or thermosetting type. The thermoplastic resins are fire resistant, hard, strong, not water soluble and may be used to make exterior fiberboard, OAS boards, plywood, molded products, etc. These urea salts of lignin may also be utilized as long acting fertilizer, to produce plastics and other products.

Abstract: Flame retardant and water resistant products are produced from bio-based materials such as lignin cellulose containing materials. The lignin cellulose materials are modified by the method of delignification. The method of this invention utilizes an amino compound in an aqueous solution to react with the lignin in the lignin cellulose and the amino lignin and freed lignin becomes water soluble. The amino compound also reacts with the non-water soluble lignin still attached to the cellulose and also to the cellulose that is produced. Other products are produced in this method such as carbohydrates, hemi-cellulose, rosins, waxes, alcohols and other products. The amino lignin, lignin, amino lignin and amino cellulose is reacted with many organic and inorganic compounds such as aldehydes, polyisocyanates, epoxies, polycarboxylic acids, vegetable oils and many other compounds to produce resins and adhesives which may be used to produce products such as molded products, particleboard, plywood, ABS, etc.

Abstract: Methods of making esterified lignocellulosic materials and resulting compositions and articles are disclosed.

Abstract: A lignophenol derivative is represented by Formula (1): wherein X1, X2 and X3 each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylene group, a hydroxyl group, a carboxyl group, an amino group, or an amide group; a and c each independently is an integer of 0 to 3; b is an integer of 0 to 4; and n is an integer of 1 to 10000.

Abstract: An organic expander composition for improving the cycle life and the cold crank ability properties of lead-acid batteries as compared to standard or oxylignin organic expanders. The organic expander composition is obtained by a blend of oxylignin and kraft lignin.

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.

Abstract: An improved non-dispersing set retarder additive for foamed cements, cement compositions containing the additive, and methods of cementing in a subterranean zone penetrated by a well bore are provided. The set retarder additive includes a blend of a sulfonated lignin, preferably a lignosulfonate, with an alkali lignin, preferably a kraft lignin, having an organic sulfur content of 0-3.5% by weight in a ratio of about 6:4 to 8:2. The methods are basically comprised of the steps of preparing a foamed cement composition comprised of hydraulic cement, a non-dispersing set retarder, sufficient water to form a slurry, sufficient gas to foam the slurry and a foaming and foam stabilizing surfactant present in an amount sufficient to facilitate the formation of the foam and stabilize the foamed cement composition.

Abstract: An organic expander composition for improving the cycle life and the cold crank ability properties of lead-acid batteries as compared to standard or oxylignin organic expanders. The organic expander composition is obtained by a blend of oxylignin and kraft lignin.

Abstract: An organic expander composition for improving the cycle life and the cold crank ability properties of lead-acid batteries as compared to standard or oxylignin organic expanders. The organic expander composition is obtained by a blend of oxylignin and kraft lignin.

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.

Abstract: A method for preparing a polymerized alkali lignin material which comprises reacting an alkaline solution of alkali lignin obtained from an alkaline pulping process at a temperature between about 20.degree. C. to 90.degree. C. with between 5% to 80% by weight based on said alkali lignin of sodium persulfate at a pH of between about 7 to 12 for a sufficient time to form a polymerized alkali lignin. Optionally, the alkaline solution of alkali lignin may be oxidized for a period time sufficient to activate the alkali lignin prior to reacting the solution with sodium persulfate.

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.

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.

Abstract: A composite molecular active substance group for use in restitutive chemotherapy against viral infections, which is produced by the process comprising: (a) preparing lignin units by carrying out an extraction in an aqueous media under weakly acidic or alkaline conditions of wood or wood-like materials and/or plant-cell cultures and separating-off the resultant insoluble solids; (b) preparing lignoid units by carrying out an aqueous alkaline extraction at a pH of 7 to 14 of starting materials selected from the group consisting of wood-incarbonization products and bioconverted wood-like materials and separating-off the resultant alkali-insoluble solids; and (c) preparing a water-soluble mixed polymer by reacting the lignin units from step (a) with the lignoid units from step (b), under aqueous alkaline isolating by ultrafiltration a low molecular weight fraction having a molecular weight of no more than 3000 daltons of the mixed polymer, taking a cut between 15 to 40 kilodaltons and discarding the resultant res

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.

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.

Abstract: A low inclusion animal feed binder composed of ozonated lignosulfonate. The ozonated lignosulfonate is a reaction product of lignosulfonate and ozone prepared by treating lignosulfonate with 2-20% ozone by weight of lignosulfonate solids at an initial pH of 2 to 12 and at a temperature of 5.degree. to 100.degree. C. The binder is incorporated with the animal feed in an amount from 0.01 to 2% by weight of dry feed.

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.

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.

Abstract: A nitrite-oxidized base lignosulfonate and a method of making the same; the method comprises providing a base lignosulfonate material and oxidizing it in the presence of sodium nitrite under alkaline conditions at a temperature greater than about 100.degree. C.; useful products of same are dispersants for dyes and dispersants for setting materials e.g. gypsum.

Abstract: A sulfonated lignin composition suitable for use as an additive in other chemical compositions and processes having improved solubility in aqueous medium at varying pH levels, and a method of producing such sulfonated water-soluble lignin products by reaction of an unsulfonated or a sulfonated starting lignin compound with sulfuric acid having a concentration of at least about 95%, while maintaining the temperature of the reaction below 40.degree. C. for a sufficient time to sulfonate the same. Sulfuric acid sulfonation increases the organically bound sulfonic acid content of the starting lignin compound at least about 1.7 moles sulfonic acid per mole of lignin, while providing water-solubility of the product at a wide range of pH levels.

Abstract: A sulfonated lignin composition suitable for use as an additive in other chemical compositions and processes having essentially complete water solubility in aqueous medium at all pH levels, and a method of producing such sulfonated water-soluble lignin products by reaction of an unsulfonated or a sulfonated starting lignin compound with oleum, while maintaining the temperature of the reaction below 40.degree. C. for a sufficient time to sulfonate the same. Oleum sulfonation provide an increases the organically bound sulfuonic acid content of the starting lignin compound of at least about 4.2 moles sulfonic acid per mole of lignin, while providing essentially complete water solubility of the product at all pH levels.

Abstract: A sulfonated lignin composition suitable for use as an additive in other chemical compositions and processes having improved solubility in aqueous medium at varying pH levels, and a method of producing such sulfonated water-soluble lignin products by reaction of an unsulfonated or a sulfonated starting lignin compound with sulfuric acid having a concentration of at least about 95%, while maintaining the temperature of the reaction below 40.degree. C. for a sufficient time to sulfonate the same. Sulfuric acid sulfonation increases the organically bound sulfonic acid content of the starting lignin compound at least about 1.7 moles sulfonic acid per mole of lignin, while providing water-solubility of the product at a wide range of pH levels.

Abstract: A sulfonated lignin composition suitable for use as an additive in other chemical compositions and processes having essentially complete water solubility in aqueous medium at all pH levels, and a method of producing such sulfonated water-soluble lignin products by reaction of an unsulfonated or a sulfonated starting lignin compound with oleum, while maintaining the temperature of the reaction below 40.degree. C. for a sufficient time to sulfonate the same. Oleum sulfonation provide an increases the organically bound sulfonic acid content of the starting lignin compound of at least about 4.2 moles sulfonic acid per mole of lignin, while providing essentially complete water solubility of the product at all pH levels.

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.

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.

Abstract: A hydraulic cement slurry is disclosed which has low fluid loss properties. In addition to water and hydraulic cement, the hydraulic cement slurry contains a fluid loss control additive comprising a sulfonated or sulfomethylated kraft lignin that has been aminated by reacting it with a polyamine and an aldehyde. The slurry also contains sodium carbonate, sodium phosphate, sodium sulfite, sodium metasilicate or naphthalene sulfonate.

Abstract: A method of producing a sulfated lignin comprising the steps of dissolving lignin in an aqueous alkaline solution, adding an organic amine-sulfur trioxide complex to the dissolved lignin, and reacting the amine-sulfur trioxide complex with the lignin under conditions to sulfate the same.

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.

Abstract: A lignin dispersion of submicron particles with film forming, binding, and adhesive properties in which the median particle diameter of the lignin in dispersion preferably is less than about 300 angstroms. The aqueous dispersion is formed by reacting about 12 to 18% lignin by weight in aqueous solution with from about 2 to 15 moles ammonia, 4 to 12 moles formaldehyde, and 0.25 to 1.25 moles sodium hydroxide or potassium hydroxide at a temperature of at least about 150.degree. F. for a period of time to produce a colloidal dispersion of lignin particles.

Abstract: A product comprising, a water insoluble lignin material, at neutral or acid pH, having chemically bound a sulfur(S) content from at least 9.5%, and a phosphorus(P) content from 3.3 to 10%. At least 50% by weight of the S and P content is thiophosphate. In said lignin material the mole ratio S/P is at least 1.8 that of S to aromatic unit (S/Ar) is greater than 0.7, and the P/Ar ratio is from 0.3 to 0.8. The lignin material has chelating capacities for gold at pH 2 of at least 2.2 millimoles per gram of lignin material. On IR analysis the lignin material has infra-red absorption bands evidencing P.dbd.S, P--S or Ar--S, P--O--Ar, aromatic, CH.sub.2 --S, and P--O--C groups in the vicinity of 730-750, 640-670, 1080-1110, 1490-1510, 820-845, and 965-995 cm.sup.-1, respectively. In the absence of interferring IR bands, the sum of the intensity of the bands in the vicinity of 640-670 cm.sup.-1 and 730-750 cm.sup.-1 over the intensity of the band in the vicinity of 1080-1110 cm.sup.-1 is greater than 1.

Abstract: A carbon black composition comprising carbon black and a lignin dispersant prepared by the steps of methylolating a lignin compound by reaction of less than about 2 moles formaldehyde per 1,000 grams of the lignin, and sulfonating the methylolated lignin by reaction from about 2.5 to 3.5 moles of the sulfite or bisulfite compound per 1,000 grams of lignin at an initial reaction pH of below about 6.6 and at a temperature of at least about 170.degree. C., while allowing the pH of the reaction mixture to rise to a final pH of greater than 7.5 to sequentially sulfomethylate the aromatic nucleus and sulfonate the side chain of the lignin.