Method for preparing a binding resin

Abstract

The present invention relates to a process for preparing a binder resin, in which lignin in the form of a solid or a dispersion in water is mixed with a crosslinking agent and optionally one or more additives, and then a basic solution is added. For example, the binder resin is useful in the production of laminates, mineral wool insulation, and wood products such as plywood, oriented strand board (OSB), laminated veneer lumber (LVL), medium density fiberboard (MDF), high density fiberboard (HDF), parquet flooring, curved plywood, veneered particleboard, veneered MDF or particleboard, laminates, or mineral wool insulation.

Description

[Technical field]

[0001] The present invention relates to a process for preparing a binding resin, in which lignin is provided in the form of a solid or a dispersion in water, the lignin being selected from the group consisting of glycerol diglycidyl ether, diglycerol polyglycidyl ether, polyglycerol polyglycidyl ether, glycerol triglycidyl ether, sorbitol polyglycidyl ether, alkoxylated glycerol polyglycidyl ethers, trimethylolpropane triglycidyl ether, trimethylolpropane diglycidyl ether, polyoxypropylene glycol diglycidyl ether, polyoxypropylene glycol triglycidyl ether, diglycidyl ether of cyclohexanedimethanol, resorcinol diglycidyl ether, isosorbide diglycidyl ether, pentaerythritol tetraglycidyl ether, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether having 2 to 9 ethylene glycol units, diglycidyl ethers, propylene glycol diglycidyl ethers having 1 to 5 propylene glycol units, hexahydrophthalic acid diglycidyl esters of terminal diols having a linear carbon chain of 3 to 6 carbon atoms and / or diglycidyl ethers of said terminal diols, or diglycidyl-, triglycidyl- or polyglycidyl-ethers of carbohydrates, diglycidyl-, triglycidyl- or polyglycidyl-esters of carbohydrates, diglycidyl ethers or diglycidyl esters of salicylic acid, vanillic acid or 4-hydroxybenzoic acid, epoxidized or glycidyl-substituted plant phenolic compounds (e.g. tannins, cardanol, cardol, anacardic acid), epoxidized vegetable oils (e.g. rapeseed oil, linseed oil, soybean oil), tris(4-hydroxyphenyl)methane triglycidyl ether, N,N-bis(2,3-epoxypropyl)aniline, p-(2,3-epoxypropoxy-N,N-bis(2,3-epoxypropyl)aniline, diglycidyl ether of bis-hydroxymethylfuran, and one or more crosslinkers having functional groups selected from diglycidyl amide, triglycidyl amide, polyglycidyl amide, diglycidyl ester, triglycidyl ester, polyglycidyl ester, diglycidyl azide, triglycidyl azide, polyglycidyl azide, diglycidyl methacrylate, triglycidyl methacrylate, and polyglycidyl methacrylate, and optionally further one or more additives, are mixed together, and then a basic solution is added. The binder resins are useful, for example, in the manufacture of laminates, mineral wool insulation, and wood products such as plywood, oriented strand board (OSB), laminated veneer lumber (LVL), medium density fiberboard (MDF), high density fiberboard (HDF), parquet flooring, curved plywood, veneered particleboard and veneered MDF, laminates or mineral wool insulation. The binder resins are also useful, for example, in composites, molding compounds, casting applications, and coatings on paper, wood or metal substrates. [Background technology]

[0002] Lignin, an aromatic polymer, is, for example, the major constituent in wood and is the most abundant carbon source on earth after cellulose. In recent years, the development and commercialization of techniques to extract lignin in a highly purified, solid, specific form from the pulp manufacturing process has attracted considerable attention as a renewable alternative to the predominantly aromatic chemical precursors currently supplied by the petrochemical industry.

[0003] Lignin, an aromatic polymer network, has been widely studied as a suitable replacement for phenol during the manufacture of phenol-formaldehyde adhesives. These are used in the manufacture of structural wood products such as plywood, oriented strand board, fiberboard, and laminates. During the synthesis of such adhesives, phenol, which may be partially replaced by lignin, reacts with formaldehyde in the presence of a basic or acidic catalyst to form highly crosslinked aromatic resins called novolacs (when an acidic catalyst is utilized) or resols (when a basic catalyst is utilized). Currently, only a limited amount of phenol can be replaced by lignin due to the low reactivity of lignin. Summary of the Invention [Problem to be solved by the invention]

[0004] One problem in preparing resins containing lignin is the use of formaldehyde when lignin is used in formaldehyde-containing resins, such as lignin-phenol-formaldehyde resins. Formaldehyde-based resins emit formaldehyde, a toxic volatile organic compound. Current or proposed legislation aimed at reducing or eliminating formaldehyde emissions has led to the development of formaldehyde-free resins for wood adhesive applications.

[0005] Jingxian Li R.et.al (Green Chemistry, 2018, 20, 1459-1466) describes the preparation of a resin containing glycerol diglycidyl ether and lignin, where the lignin is provided in a solid form. One problem with the technique described in this paper is the long pressing times and high pressing temperatures. Three-ply plywood samples were pressed at a temperature of 150°C for 15 minutes to allow the resin to fully cure.

[0006] Engelmann G. and Ganster J. (Holzforschung, 2014, 68, 435-446) describe the preparation of bio-based epoxy resins using low molecular weight kraft lignin and pyrogallol, where the lignin component consists of an acetone extractable from kraft lignin. [Means for solving the problem]

[0007] Surprisingly, it has now been found that when lignin is dispersed in a suitable crosslinking agent, such as a glycidyl ether, the crosslinking reaction can be catalyzed by a basic solution, resulting in a fast-curing resin with excellent reactivity, adhesive strength, and water resistance.

[0008] When the lignin dispersed in glycidyl ether is mixed with water or alkali, the lignin dissolves in the basic solution. In addition, the phenolic hydroxyl groups in the lignin structure are deprotonated and are free to react with the epoxide groups of the glycidyl ether. This catalyzes the reaction and improves the reactivity and performance of the binder. Thus, the binding resin can be easily prepared and the use of formaldehyde can be avoided. The binding resin according to the invention significantly accelerates the reaction and therefore allows the use of shorter pressing times and lower pressing temperatures to cure the binding resin when producing laminates, mineral wool insulation, and wood products such as plywood, oriented strand board (OSB), laminated veneer lumber (LVL), medium density fiberboard (MDF), parquet flooring, curved plywood, veneered particleboard, veneered MDF, or particleboard, laminates or mineral wool insulation. The bonded resins are also useful, for example, in composites, molding compounds, foundry applications, and for coating paper, wood or metal substrates.

[0009] Accordingly, the present invention relates to the following: 1. A method for preparing a binding resin comprising the steps of: Lignin in the form of a solid or a dispersion in water is Glycerol diglycidyl ether, diglycerol polyglycidyl ether, polyglycerol polyglycidyl ether, glycerol triglycidyl ether, sorbitol polyglycidyl ether, alkoxylated glycerol polyglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolpropane diglycidyl ether, polyoxypropylene glycol diglycidyl ether, polyoxypropylene glycol triglycidyl ether, diglycidyl ether of cyclohexane dimethanol, resorcinol diglycidyl ether glycidyl ether, isosorbide diglycidyl ether, pentaerythritol tetraglycidyl ether, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether having 2 to 9 ethylene glycol units, propylene glycol diglycidyl ether having 1 to 5 propylene glycol units, hexahydrophthalic acid diglycidyl esters of terminal diols having a linear carbon chain of 3 to 6 carbon atoms and / or diglycidyl ethers of such terminal diols, or diglycidyl- and triglycidyl esters of carbohydrates. diglycidyl- or polyglycidyl-ethers, diglycidyl-, triglycidyl- or polyglycidyl-esters of carbohydrates, diglycidyl ethers or esters of salicylic acid, vanillic acid, or 4-hydroxybenzoic acid, epoxidized or glycidyl-substituted plant phenolic compounds (e.g., tannins, cardanol, cardol, anacardic acid), epoxidized vegetable oils (e.g., rapeseed oil, linseed oil, soybean oil), tris(4-hydroxyphenyl)methane triglycidyl ether, N,N-bis(2,3-epoxypropyl)aniline, p-(2,3-epoxypropoxy-N,N-bis(2,3-epoxypropyl)aniline, diglycidyl ether of bis-hydroxymethylfuran, and one or more crosslinkers having functional groups selected from diglycidyl amide, triglycidyl amide, polyglycidyl amide, diglycidyl ester, triglycidyl ester, polyglycidyl ester, diglycidyl azide, triglycidyl azide, polyglycidyl azide, diglycidyl methacrylate, triglycidyl methacrylate, and polyglycidyl methacrylate; then adding a basic solution; The above method.

[0010] One aspect of the invention is a method for preparing a binding resin, in which solid lignin is mixed with one or more crosslinking agents and / or one or more glycidyl ethers, the crosslinking agents having an epoxy equivalent of more than 4 equivalents / kg, and then a basic solution is added. The epoxy equivalent (epoxy value) can be measured according to ISO 3001. Preferably, the crosslinking agent has an epoxy equivalent of more than 5 equivalents / kg. The crosslinking agent is an aliphatic or preferably aromatic glycidyl ether. Preferably, the crosslinking agent is aliphatic.

[0011] The glycidyl ether may be a polyfunctional epoxide. The process according to the invention may use mixtures of epoxides, such as, for example, monofunctional, difunctional, trifunctional and / or tetrafunctional.

[0012] Therefore, the present invention also relates to the binding resin obtained using the above method. Furthermore, the present invention relates to the use of said binding resin in the manufacture of laminates, mineral wool insulation, and wood products such as plywood, oriented strand board (OSB), laminated veneer lumber (LVL), medium density fiberboard (MDF), and particle board. The binding resin according to the present invention can also be used in or for coatings, such as coatings applied on metal surfaces or on wood or other substrates. The present invention also relates to such laminates, mineral wool insulation, and wood products, such as plywood, oriented strand board (OSB), laminated veneer lumber (LVL), medium density fiberboard (MDF), high density fiberboard (HDF), parquet flooring, curved plywood, veneered particleboard, veneered MDF, laminates or mineral wool insulation, manufactured with said binding resin. The binding resin according to the present invention can also be used in the manufacture of composites, moulding compounds, casting applications, and coatings for paper, wood or metal substrates. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] Throughout the present specification, the expression "lignin" is intended to encompass any type of lignin, for example lignin derived from hardwoods (broadleaf trees), softwoods (conifers) or annular plants. Preferably, the lignin is alkaline lignin, for example produced in the Kraft process. Preferably, the lignin is purified or isolated before being used in the process according to the invention. The lignin may be isolated from black liquor and, optionally, may be further purified before being used in the process according to the invention. The purification is typically carried out so that the purity of the lignin is at least 90%, preferably at least 95%. Thus, preferably, the lignin used according to the method of the invention contains less than 10%, preferably less than 5%, of impurities. The lignin can then be separated from the black liquor by using the process disclosed in WO2006 / 031175. The lignin can then be separated from the black liquor using a process called the LignoBoost process.

[0014] The particle size of the lignin is preferably such that 50% by weight of the particles have a particle size greater than 100 micrometers. Preferably, at least 20% by weight of the particles have a particle size greater than 300 micrometers. Preferably, at least 80% by weight of the particles have a particle size less than 1000 micrometers. Preferably, the moisture content of the particles is less than 40% by weight.

[0015] Glycerol diglycidyl ether, diglycerol polyglycidyl ether, polyglycerol polyglycidyl ether, glycerol triglycidyl ether, sorbitol polyglycidyl ether, alkoxylated glycerol polyglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolpropane diglycidyl ether, polyoxypropylene glycol diglycidyl ether, polyoxypropylene glycol triglycidyl ether, diglycidyl ether of cyclohexanedimethanol, resorcinol diglycidyl ether, isosorbide diglycidyl ether, pentaerythritol tetraglycidyl ether , ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether having 2-9 ethylene glycol units (preferably having 2-5 ethylene glycol units, e.g., having 2-3 ethylene glycol units or having 4-5 ethylene glycol units), propylene glycol diglycidyl ether having 1-3 propylene glycol units or having 4-5 propylene glycol units, hexahydrophthalic acid diglycidyl ester of a terminal diol having a linear carbon chain of 3-6 carbon atoms and / or diglycidyl ether of said terminal diol are used according to the present invention to function as crosslinkers. Glycidyl ethers having multiple epoxide functional groups, such as glycerol diglycidyl ether, glycerol triglycidyl ether, and sorbitol polyglycidyl ether, can be used. Other glycidyl ethers having 2-9 (e.g., 2-4 or 2-6) alkylene glycol groups can be used, such as diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, and tripropylene diglycidyl ether. The longer the chain length between the two glycidyl ether groups, the more flexible the resin will be, which can negatively affect the performance of the resin. This results in an adhesive (tackifier) ​​during curing.Diglycidyl-, triglycidyl-, or polyglycidyl-ethers of carbohydrates, diglycidyl-, triglycidyl-, or polyglycidyl-esters of carbohydrates, diglycidyl ethers or esters of salicylic acid, vanillic acid, or 4-hydroxybenzoic acid, epoxidized or glycidyl-substituted plant-based phenolic compounds (e.g., tannins, cardanol, cardol, anacardic acid), epoxidized vegetable oils (e.g., rapeseed oil, linseed oil, soybean oil), tris(4-hydroxyphenyl)methane triglycidyl ether, N,N-bis(2,3-epoxypropyl)aniline, p-(2,3-epoxypropoxy-N,N-bis(2,3-epoxypropyl)aniline, bis-hydroxyphenyl Crosslinkers selected from diglycidyl ethers of dimethylfuran, and crosslinkers having functional groups selected from diglycidyl amides, triglycidyl amides, polyglycidyl amides, diglycidyl esters, triglycidyl esters, polyglycidyl esters, diglycidyl azides, triglycidyl azides, polyglycidyl azides, diglycidyl methacrylates, triglycidyl methacrylates, and polyglycidyl methacrylates, may be used according to the present invention. This results in an adhesive during curing. Typically, the binding resin according to the present invention is applied to the surface of, for example, a veneer, such as in the manufacture of plywood. When multiple veneers are pressed together while being heated, crosslinking in the binding resin occurs, producing an adhesive.

[0016] The pH of the basic solution is preferably in the range of 10 to 14. Examples of suitable bases include sodium hydroxide, potassium hydroxide, ammonia or other organic bases, and mixtures thereof. In one embodiment, the amount of alkali in the basic solution is preferably 0.1% to 15% by weight of the solution, such as 0.1% to 10% by weight of the solution. In one embodiment, the basic solution is an aqueous solution. The basic solution may contain additives such as urea, tannins, solvents, surfactants, dispersants, and fillers.

[0017] Lignin (dry weight) and glycerol diglycidyl ether, diglycerol polyglycidyl ether, polyglycerol polyglycidyl ether, glycerol triglycidyl ether, sorbitol polyglycidyl ether, alkoxylated glycerol polyglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolpropane diglycidyl ether, polyoxypropylene glycol diglycidyl ether, polyoxypropylene glycol triglycidyl ether, diglycidyl ether of cyclohexanedimethanol, resorcinol diglycidyl ether, isosorbide diglycidyl ether, pentaerythritol tetraglycidyl ether, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether having 2 to 9 ethylene glycol units, and polyethylene glycol diglycidyl ether having 1 to 5 propylene glycol units. Propylene glycol diglycidyl ether, hexahydrophthalic acid diglycidyl esters of terminal diols having a linear carbon chain of 3 to 6 carbon atoms and / or diglycidyl ethers of said terminal diols, or diglycidyl-, triglycidyl- or polyglycidyl-ethers of carbohydrates, diglycidyl-, triglycidyl- or polyglycidyl-esters of carbohydrates, diglycidyl ethers or esters of salicylic acid, vanillic acid or 4-hydroxybenzoic acid, epoxidized or glycidyl-substituted plant phenolic compounds (e.g., tannins, cardanol, cardol, anacardic acid), epoxidized vegetable oils (e.g., rapeseed oil, linseed oil, soybean oil), tris(4-hydroxyphenyl)methane triglycidyl ether, N,N-bis(2,3-epoxypropyl)aniline, p-(2,3-epoxypropoxy-N,N-bis(2,The weight ratio of the total weight of the crosslinking agent having a functional group selected from 3-epoxypropyl)aniline, diglycidyl ether of bis-hydroxymethylfuran, and diglycidyl amide, triglycidyl amide, polyglycidyl amide, diglycidyl ester, triglycidyl ester, polyglycidyl ester, diglycidyl azide, triglycidyl azide, polyglycidyl azide, diglycidyl methacrylate, triglycidyl methacrylate, and polyglycidyl methacrylate is preferably in the range of 1:10 to 10:1. The amount of lignin in the binding resin is preferably 5% by weight to 50% by weight, calculated as the dry weight of lignin based on the total weight of the binding resin.

[0018] The bond resin may also contain additives such as urea, tannins, solvents and fillers.

[0019] The amount of urea in the binding resin may be 0-40%, preferably 5-20%, calculated as the dry weight of urea based on the total weight of the binding resin.

[0020] Fillers and / or hardeners may also be added to the binding resin, examples of which include limestone, cellulose, sodium carbonate, and starch.

[0021] The reactivity of lignin with glycidyl ethers can be increased by modifying the lignin by glyoxylation, etherification, esterification, or any other method that increases the hydroxyl, carboxyl, amine, or thiol content of the lignin.

[0022] Other solvents that may be used with the binding resin according to the present invention may be glycerol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, sorbitol, and / or any terminal diol having a linear carbon chain of 3 to 6 carbon atoms.

[0023] The lignin in the form of a solid or a dispersion in water is preferably mixed with the glycidyl ether at room temperature, such as at a temperature between 15° C. and 30° C. The mixing is preferably carried out for about 5 minutes to 2 hours. Preferably, the viscosity of the mixture is monitored during mixing, either continuously or by taking a sample and measuring its viscosity. After the addition of the basic solution, the mixing is preferably carried out for at least 1 minute, for example for 1 minute to about 2 hours. Preferably, the viscosity of the mixture is also monitored during mixing after the addition of the basic solution, either continuously or by taking a sample and measuring its viscosity. The mixing can also be carried out by providing the glycidyl ether on the lignin particles, for example by spraying the glycidyl ether on the lignin particles, optionally followed by drying. EXAMPLES

[0024] Working Example The first component was prepared by dispersing 40 g of lignin in 60 g of polyglycerol polyglycidyl ether and 30 g of glycerol. The second component was prepared by mixing 17.4 g of 50% sodium hydroxide solution with 49.8 g of water. Both components were mixed and stirred at room temperature using an overhead stirrer for 20 minutes.

[0025] The binders were subjected to lap joint testing using an Automated Bonding Evaluation System (ABES) tensile tester.

[0026] For this purpose, a relatively thin sheet of beech veneer with a thickness of 0.6 mm was used and cut into pieces measuring 105 x 20 mm. Resin was applied to an area of ​​5 mm x 20 mm on one side of one end of the two pieces. The resin-coated overlapping ends of a series of specimens were pressed with a pressure of 5 kg / m using a press temperature of 150°C and a press time of 90 seconds. 2 The pieces were pressed together in a hot press at a pressure of 1000 .mu.m.

[0027] All samples were soaked in water for 24 hours at room temperature prior to evaluation. Average data from five specimens with and without conditioning are shown in Table 1.

[0028] [Table 1]

[0029] Example 2 The first component was prepared by dispersing 40 g of lignin in 60 g of polyethylene glycol diglycidyl ether. The second component was prepared by mixing 22.6 g of 50% sodium hydroxide solution with 80 g of water. The first and second components were mixed and stirred at room temperature using an overhead stirrer for 20 minutes.

[0030] The binders were subjected to lap joint testing using an Automated Bonding Evaluation System (ABES) tensile tester.

[0031] For this purpose, a relatively thin sheet of beech veneer with a thickness of 0.6 mm was used and cut into pieces measuring 105 x 20 mm. Resin was applied to an area of ​​5 mm x 20 mm on one side of one end of the two pieces. The resin-coated overlapping ends of a series of specimens were pressed with a pressure of 5 kg / m using a press temperature of 150°C and a press time of 90 seconds. 2 The pieces were pressed together in a hot press at a pressure of 1000 .mu.m.

[0032] All samples were soaked in water for 24 hours at room temperature prior to evaluation. Average data from five specimens with and without conditioning are shown in Table 2.

[0033] [Table 2]

[0034] Other modifications and variations will be apparent to those skilled in the art in view of the above detailed description of the invention. It should be apparent, however, that such other modifications and variations can be made without departing from the spirit and scope of the invention. One embodiment of the present invention will be described below, but the present invention is not limited thereto. [Invention 1] 1. A method for preparing a binding resin comprising the steps of: Lignin in the form of a solid or a dispersion in water is Glycerol diglycidyl ether, diglycerol polyglycidyl ether, polyglycerol polyglycidyl ether, glycerol triglycidyl ether, sorbitol polyglycidyl ether, alkoxylated glycerol polyglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolpropane diglycidyl ether, polyoxypropylene glycol diglycidyl ether, polyoxypropylene glycol triglycidyl ether, diglycidyl ether of cyclohexanedimethanol, resorcinol diglycidyl ether, isosorbide diglycidyl ether, pentaerythritol tetraglycidyl ether, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether having 2 to 9 ethylene glycol units, propylene glycol diglycidyl ether having 1 to 5 propylene glycol units Lithium diglycidyl ether, hexahydrophthalic acid diglycidyl esters of terminal diols having a linear carbon chain of 3 to 6 carbon atoms and / or diglycidyl ethers of said terminal diols, or diglycidyl-, triglycidyl- or polyglycidyl-ethers of carbohydrates, diglycidyl-, triglycidyl- or polyglycidyl-esters of carbohydrates, diglycidyl ethers or esters of salicylic acid, vanillic acid or 4-hydroxybenzoic acid, epoxidized or glycidyl-substituted plant phenolic compounds (e.g., tannins, cardanol, cardol, anacardic acid), epoxidized vegetable oils (e.g., rapeseed oil, linseed oil, soybean oil), tris(4-hydroxyphenyl)methane triglycidyl ether, N,N-bis(2,3-epoxypropyl)aniline, p-(2,3-epoxypropoxy-N,N-bis(2,3-epoxypropyl)aniline, diglycidyl ether of bis-hydroxymethylfuran, and one or more crosslinkers having functional groups selected from diglycidyl amide, triglycidyl amide, polyglycidyl amide, diglycidyl ester, triglycidyl ester, polyglycidyl ester, diglycidyl azide, triglycidyl azide, polyglycidyl azide, diglycidyl methacrylate, triglycidyl methacrylate, and polyglycidyl methacrylate, and optionally further one or more additives; then adding a basic solution; The above method. [Invention 2] The solid lignin Glycerol diglycidyl ether, diglycerol polyglycidyl ether, polyglycerol polyglycidyl ether, glycerol triglycidyl ether, sorbitol polyglycidyl ether, alkoxylated glycerol polyglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolpropane diglycidyl ether, polyoxypropylene glycol diglycidyl ether, polyoxypropylene glycol triglycidyl ether, diglycidyl ether of cyclohexane dimethanol, resorcinol diglycidyl ether ter, isosorbide diglycidyl ether, pentaerythritol tetraglycidyl ether, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether having 2 to 9 ethylene glycol units, propylene glycol diglycidyl ether having 1 to 5 propylene glycol units, hexahydrophthalic acid diglycidyl ester of a terminal diol having a linear carbon chain of 3 to 6 carbon atoms and / or diglycidyl ether of said terminal diol, and optionally further comprising one or more additives; A basic solution is then added, The method according to claim 1. [Invention 3] 3. The method according to claim 1 or 2, wherein the ether is a polyglycerol polyglycidyl ether. [Invention 4] 4. The method according to any one of claims 1 to 3, wherein one additive is a solvent. [Invention 5] 5. The method according to any one of claims 1 to 4, wherein the weight ratio of the weight of lignin, calculated on the basis of dry lignin, to the total weight of glycerol diglycidyl ether and / or ethylene glycol diglycidyl ether is 1:10 to 10:1. [Invention 6] 6. The method according to any one of claims 1 to 5, wherein one additive is urea, tannin, a surfactant, a dispersant, a filler and / or a solvent. [Invention 7] 7. The method according to claim 6, wherein the solvent is glycerol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, sorbitol, and / or any terminal diol having a linear carbon chain of 3 to 6 carbon atoms. [Invention 8] 8. The method according to any one of claims 1 to 7, wherein the lignin has been modified by glyoxylation, etherification, esterification or any other means to increase the hydroxyl or carboxyl or amine or thiol content of the lignin. [Invention 9] 1. A method for preparing a binding resin comprising the steps of: mixing solid lignin with one or more crosslinking agents and / or one or more glycidyl ethers and then adding a basic solution, wherein the crosslinking agent has an epoxy equivalent weight of greater than 4 equivalents / kg; The above method. [Invention 10] A binding resin obtained by the method according to any one of claims 1 to 9. [Invention 11] Use of the binding resin according to invention 10 in the manufacture of laminates, mineral wool insulation and wood products such as plywood, oriented strand board (OSB), laminated veneer lumber (LVL), medium density fiberboard (MDF), high density fiberboard (HDF), parquet flooring, curved plywood, veneered particleboard and veneered MDF, laminates or mineral wool insulation. [Invention 12] 11. Use of the binding resin according to invention 10 in the manufacture of laminates, mineral wool insulation and wood products such as plywood, oriented strand board (OSB), laminated veneer lumber (LVL), medium density fiberboard (MDF), high density fiberboard (HDF), parquet flooring, curved plywood, veneered particleboard, veneered MDF or particleboard, laminates or mineral wool insulation, wherein the binding resin is provided to a surface and when the surface is exposed to pressure and heat, curing of the binding resin to form an adhesive occurs. [Invention 13] 13. Laminates, mineral wool insulation and wood products such as plywood, oriented strand board (OSB), laminated veneer lumber (LVL), medium density fiberboard (MDF), high density fiberboard (HDF), parquet flooring, curved plywood, veneered particleboard, veneered MDF or particleboard, laminates or mineral wool insulation produced using the binding resins according to claim 12.

Claims

1. 1. A method for preparing a binding resin comprising the steps of: Lignin in the form of a solid or a dispersion in water is Glycerol diglycidyl ether, diglycerol polyglycidyl ether, polyglycerol polyglycidyl ether, glycerol triglycidyl ether, sorbitol polyglycidyl ether, alkoxylated glycerol polyglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolpropane diglycidyl ether, polyoxypropylene glycol diglycidyl ether, polyoxypropylene glycol triglycidyl ether, diglycidyl ether of cyclohexanedimethanol, resorcinol diglycidyl ether, isosorbide diglycidyl ether, pentaerythritol tetraglycidyl ether, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether having 2 to 9 ethylene glycol units, propylene glycol diglycidyl ether having 1 to 5 propylene glycol units Lithol diglycidyl ether, hexahydrophthalic acid diglycidyl esters of terminal diols having a linear carbon chain of 3 to 6 carbon atoms and / or diglycidyl ethers of said terminal diols, or diglycidyl-, triglycidyl- or polyglycidyl-ethers of carbohydrates, diglycidyl-, triglycidyl- or polyglycidyl-esters of carbohydrates, diglycidyl ethers or esters of salicylic acid, vanillic acid or 4-hydroxybenzoic acid, epoxidized or glycidyl-substituted plant phenolic compounds (such as tannins, cardanol, cardol, anacardic acid), epoxidized vegetable oils (such as rapeseed oil, linseed oil, soybean oil), tris(4-hydroxyphenyl)methane triglycidyl ether, N,N-bis(2,3-epoxypropyl)aniline, p-(2,3-epoxypropoxy-N,N-bis(2,3-epoxypropyl)aniline, diglycidyl ether of bis-hydroxymethylfuran, and one or more crosslinkers having functional groups selected from diglycidyl amide, triglycidyl amide, polyglycidyl amide, diglycidyl ester, triglycidyl ester, polyglycidyl ester, diglycidyl azide, triglycidyl azide, polyglycidyl azide, diglycidyl methacrylate, triglycidyl methacrylate, and polyglycidyl methacrylate, and optionally further one or more additives; then adding an aqueous solution of sodium hydroxide having a pH in the range of 10 to 14; The above method.

2. The solid lignin Glycerol diglycidyl ether, diglycerol polyglycidyl ether, polyglycerol polyglycidyl ether, glycerol triglycidyl ether, sorbitol polyglycidyl ether, alkoxylated glycerol polyglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolpropane diglycidyl ether, polyoxypropylene glycol diglycidyl ether, polyoxypropylene glycol triglycidyl ether, diglycidyl ether of cyclohexane dimethanol, resorcinol diglycidyl ether ter, isosorbide diglycidyl ether, pentaerythritol tetraglycidyl ether, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether having 2 to 9 ethylene glycol units, propylene glycol diglycidyl ether having 1 to 5 propylene glycol units, hexahydrophthalic acid diglycidyl esters of terminal diols having a linear carbon chain of 3 to 6 carbon atoms and / or diglycidyl ethers of said terminal diols, and optionally further with one or more additives; Then, an aqueous solution of sodium hydroxide having a pH in the range of 10 to 14 is added. The method of claim 1.

3. 3. The method of claim 1 or 2, wherein the ether is a polyglycerol polyglycidyl ether.

4. The method of any one of claims 1 to 3, wherein one additive is a solvent.

5. 5. The method according to claim 1, wherein the weight ratio of the weight of lignin calculated on dry lignin to the total weight of glycerol diglycidyl ether and / or ethylene glycol diglycidyl ether is from 1:10 to 10:

1.

6. The method according to any one of claims 1 to 5, wherein one additive is urea, tannin, a surfactant, a dispersant, a filler and / or a solvent.

7. 7. The method of claim 6, wherein the solvent is glycerol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, sorbitol, and / or any terminal diol having a linear carbon chain of 3 to 6 carbon atoms.

8. 8. The method of any one of claims 1 to 7, wherein the lignin has been modified by glyoxylation, etherification, esterification or any other means to increase the hydroxyl or carboxyl or amine or thiol content of the lignin.

9. 1. A method for preparing a binding resin comprising the steps of: mixing solid lignin with one or more crosslinking agents and / or one or more glycidyl ethers and then adding an aqueous sodium hydroxide solution having a pH in the range of 10 to 14, the crosslinking agent having an epoxy equivalent weight of greater than 4 equivalents / kg; The above method.

10. 10. Use of the binding resin obtained by the method according to any one of claims 1 to 9 in the manufacture of laminates, mineral wool insulation and wood products such as plywood, oriented strand board (OSB), laminated veneer lumber (LVL), medium density fibreboard (MDF), high density fibreboard (HDF), parquet flooring, curved plywood, veneered particleboard and veneered MDF, laminates or mineral wool insulation.

11. 10. Use of the binding resin obtained by the method according to any one of claims 1 to 9 in the manufacture of laminates, mineral wool insulation and wood products such as plywood, oriented strand board (OSB), laminated veneer lumber (LVL), medium density fibreboard (MDF), high density fibreboard (HDF), parquet flooring, curved plywood, veneered particleboard, veneered MDF or particleboard, laminates or mineral wool insulation, where the binding resin is provided to a surface and when the surface is exposed to pressure and heat, hardening of the binding resin to form an adhesive occurs.

12. 10. A method for producing laminates, mineral wool insulation and wood products such as plywood, oriented strand board (OSB), laminated veneer lumber (LVL), medium density fiberboard (MDF), high density fiberboard (HDF), parquet flooring, curved plywood, veneered particle board, veneered MDF or particle board, laminates or mineral wool insulation comprising the step of using a binding resin obtainable by the method according to any one of claims 1 to 9.

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