Abstract: A method for the enhanced recovery of oil comprised of injecting into an oil containing formation an aqueous surfactant system comprised of a blend of an oil soluble amine, a lignin selected from the group consisting of lignosulfonates and sulfonated alkali and soda lignins, and a water soluble anionic or non-ionic surfactant and water; driving the surfactant system through the formation and producing the oil mobilized by the surfactant system. A surfactant composition useful for enhanced oil recovery methods comprised of an oil soluble amine, a lignin, and a water soluble anionic or non-ionic surfactant.

Abstract: A binder composed of a graft copolymer of high molecular weight sulfonated lignin material and an acrylic compound. At least 35% by weight of the lignin material has a molecular weight in excess of 5,000 daltons. The binder is produced by reacting the high molecular weight sulfonated lignin material with 0.0125 to 0.5 parts, per part of lignin material, of acrylic acid, methyacrylic acid or acrylonitrile. A process for making the binder is also disclosed.

Abstract: Synthetic inorganic chemical fertilizers are treated with lignosulfonate to harden and provide anticaking and anti-dusting properties to the fertilizer particles. The fertilizer/lignosulfonate mixture includes up to about 5.0% by weight lignosulfonate on fertilizer. An improved method of treating inorganic fertilizers with lignosulfonate is also disclosed.

Abstract: An additive for oil well drilling cement is provided by an azo lignosulfonate formed from the coupling of a diazonium salt made from sulfanilic acid or para-aminobenzoic acid and a lignosulfonate to provide an effective cement dispersant with low set time retardation.

Abstract: A deicing composition comprising saccharinic acid, lignosulfonate and an alkali metal or alkaline earth metal chloride selected from among sodium chloride, magnesium chloride, calcium chloride and mixtures thereof, the ratio of said saccharinic acid, lignosulfonate and chloride being from about 0.05:0.95:15 to about 0.75:2.25:1. The composition has a pH value of from about 5.0 to 9.5. The saccharinic acid contemplated for use in the composition is isosaccharinic or metasaccharinic acid, or mixtures thereof. The saccharinic acid may be conveniently derived from the alkali treatment of monosaccharides and oligosaccharides inherently contained in spent sulfite liquor by heating at a temperature of 50.degree. C. to 150.degree. C., preferably at 80.degree. C. to 100.degree. C.

Abstract: A hydrolyzed lignosulfonate-acrylonitrile graft copolymer matrix providing a slow release solubility to fertilizers. The hydrolysis of the graft copolymer of lignosulfonate and acrylonitrile may be carried out in the presence of an alkali in situ during the fertilizer manufacturing process or in a prehydrolysis step with subsequent use of the hydrolyzed copolymer in the fertilizer manufacturing process to provide a controlled release formulation for various fertilizers.

Abstract: A hydrolyzed lignosulfonate-acrylonitrile graft copolymer matrix providing a slow release solubility to fertilizers. The hydrolysis of the graft copolymer of lignosulfonate and acrylonitrile may be carried out in the presence of an alkali in situ during the fertilizer manufacturing process or in a prehydrolysis step with subsequent use of the hydrolyzed copolymer in the fertilizer manufacturing process to provide a controlled release formulation for various fertilizers.

Abstract: A hydrolyzed lignosulfonate-acrylonitrile graft copolymer matrix providing slow release solubility to urea fertilizer. The hydrolysis of the graft copolymer of lignosulfonate and acrylonitrile may be carried out in the presence of a caustic in situ during the urea prill manufacturing process or in a prehydrolysis step with subsequent use of the hydrolyzed copolymer in the urea prill manufacturing process to provide the controlled release formulation for urea.

Abstract: Disclosed herein are sulfonated ligno-aminodicarboxylic acid and the salts thereof of the formula ##STR1## wherein X is an alkali cation, such as sodium, potassium, lithium, and ammonium, and Lignin denotes the polymeric sulfonated lignin material derived from commercial pulping of wood, straw, corn stalks, bagasse and the like. The dicarboxylic acid is made by a three-step process: (1) amination with ammonia and formaldehyde; (2) cyanomethylation with formaldehyde and sodium cyanide; and (3) hydrolysis of nitrile to carboxylic acid. The sulfonated ligno-aminodicarboxylic acid and its salts are useful as metal complexing agents.

Abstract: A stable lignosulfonate emulsion for use as a binding agent includes an aqueous dispersion of lignosulfonate containing material having an initial solids concentration of between about 45% to about 65% by weight, and about 1 part to about 50 parts, per 100 parts of the lignosulfonate containing material, of a hydrophobe such as wax, oil, fat, asphalt or mixtures thereof. Spray drying the emulsion provides a powder which is less dusty than comparable lignosulfonate products similarly dried, and which upon rewetting provides a stable emulsion. A method of preparing the emulsion is also disclosed.

Abstract: A method of enhanced oil recovery comprising injecting a surfactant system comprised of an oxidized alkali lignin and an anionic and/or nonionic surfactant into a formation containing oil and producing the oil thus mobilized.

Abstract: A reaction product and process for making the same of a lignosulfonate with an unsaturated fatty amine of 18 to 20 carbon atoms and an aldehyde. The process includes forming an aqueous solution of lignosulfonate at a solids concentration of 20% to 40%, adjusting the pH of the solution to above 10 or below 5, mixing the solution with a specified quantity of fatty amine to form a homogeneous mixture, adding the aldehyde to the mixture, and finally heating the mixture at a temperature of 25.degree. C. to 100.degree. C. for a period of one to 24 hours.

Abstract: A method for the enhanced recovery of oil comprised of injecting into an oil containing formation a surfactant system comprised of an oil soluble amine modified lignin and an anionic or nonionic surfactant; driving the surfactant system through the formation and producing the oil mobilized by the surfactant system. A surfactant composition useful for enhanced oil recovery methods comprised of an oil soluble amine modified lignin and an anionic or nonionic surfactant.

Abstract: A high quality chrome lignosulfonate for use as an oil well drilling additive is produced from molecular weight and/or high carbohydrate containing spent sulfite liquor. The additive is obtained by adding boron prior to the oxidation of the lignosulfonate and complexing with chrome. The use of boron allows the raw material spent sulfite liquor source to be less pure and from a wide variety of wood.

Abstract: Dispersants, especially well suited for use with insoluble dyes, are produced by reacting hydroxyl benzyl alcohol compounds with sulfonated lignin derivatives. The dispersants have high levels of heat stability, coupled with desirable dye reduction, staining, foaming, milling and viscosity-reducing properties. Dyestuffs, dye pastes and dye baths, as well as methods utilizing them, are provided.

Abstract: Improved drilling fluid additives or conditioners are obtained by oxidation of sulfonated lignin-containing materials with manganese dioxide and boron addition either before or after the oxidation step. The resulting manganese-boron lignosulfonates are more thermally stable and they are rheologically suitable as drilling fluid additives. Additional improvements in thermal stability and rheological properties are realized by complexing the manganese-boron lignosulfonates with a heavy metal cation, notably, iron, preferably used as ferrous sulfate.

Abstract: Cationic reaction products having improved flocculating performance for suspended solids are obtained by the reaction of kraft lignin with aldehydes and polyamines.

Abstract: Drilling fluid additives are prepared by oxidation of sulfonated lignin-containing materials with manganese dioxide under highly acidic conditions to make manganese lignosulfonates. Additional improvements in the rheological properties of the additives may be obtained by complexing the manganese lignosulfonate so obtained with a heavy metal cation (preferably iron or copper), by, for example, addition of ferrous sulfate or ferric sulfate to the manganese lignosulfonate. These products show the requisite combination of rheological properties for a satisfactory drilling fluid additive or conditioner.

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.

Abstract: Valuable new and widely used compositions of matter are comprised of products having enhanced solubility and increased dispersant and the like surfactant activity which products are resulfonated units of alkaline oxidized, hydrolyzed, partially desulfonated lignosulfonates.