SE545325C2 - Process for the preparation of a bonding resin - Google Patents
Process for the preparation of a bonding resinInfo
- Publication number
- SE545325C2 SE545325C2 SE1951516A SE1951516A SE545325C2 SE 545325 C2 SE545325 C2 SE 545325C2 SE 1951516 A SE1951516 A SE 1951516A SE 1951516 A SE1951516 A SE 1951516A SE 545325 C2 SE545325 C2 SE 545325C2
- Authority
- SE
- Sweden
- Prior art keywords
- lignin
- bonding resin
- ether
- mdf
- veneered
- Prior art date
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J197/00—Adhesives based on lignin-containing materials
- C09J197/005—Lignin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27N—MANUFACTURE BY DRY PROCESSES OF ARTICLES, WITH OR WITHOUT ORGANIC BINDING AGENTS, MADE FROM PARTICLES OR FIBRES CONSISTING OF WOOD OR OTHER LIGNOCELLULOSIC OR LIKE ORGANIC MATERIAL
- B27N3/00—Manufacture of substantially flat articles, e.g. boards, from particles or fibres
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B21/00—Layered products comprising a layer of wood, e.g. wood board, veneer, wood particle board
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G1/00—Lignin; Lignin derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L97/00—Compositions of lignin-containing materials
- C08L97/005—Lignin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D197/00—Coating compositions based on lignin-containing materials
- C09D197/005—Lignin
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Forests & Forestry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The present invention relates to a process for preparing a bonding resin, wherein lignin is provided in the form of a solution in ammonia and/or an organic base and mixed with one or more crosslinkers and optionally one or more additives. The bonding resin is useful for example in the manufacture of laminates, mineral wool insulation and wood products such as plywood, oriented strandboard (OSB), laminated veneer lumber (LVL), medium density fiberboards (MDF), high density fiberboards (HDF), parquet flooring, curved plywood, veneered particleboards, veneered MDF or particle boards. The bonding resin is also useful for example in composites, molding compounds and foundry applications.
Description
PROCESS FOR THE PREPARATION OF A BONDING RESIN Field of the invention The present invention relates to a process for preparing a bonding resin, wherein lignin is provided in the form of a solution in ammonia and/or an organic base and mixed with one or more crosslinker selected from polyglycerol diglycidyl ether, polyglycerol polyglycidyl ether, glycerol triglycidyl ether, alkoxylated glycerol polyglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolpropane diglycidyl ether, polyoxypropylene glycol triglycidyl ether, diglycidylether of cyclohexane dimethanol, resorcinol diglycidyl ether, isosorbide diglycidyl ether or pentaerythritol tetraglycidyl ether and optionally one or more additives, wherein the lignin has been generated in the Kraft process and is optionally modified by glyoxylation, etherification or esterification. The bonding resin is useful for example in the manufacture of laminates, mineral wool insulation and wood products such as plywood, oriented strandboard (OSB), laminated veneer Iumber (LVL), medium density fiberboards (MDF), high density fiberboards (HDF), parquet flooring, curved plywood, veneered particleboards, veneered MDF or particle boards. The bonding resin is also useful for example in composites, molding compounds and foundry applications.
Background Lignin, an aromatic polymer is a major constituent in e.g. wood, being the most abundant carbon source on Earth second only to cellulose. ln recent years, with development and commercialization of technologies to extract lignin in a highly purified, solid and particularized form from the pulp-making process, it has attracted significant attention as a possible renewable substitute to primarily aromatic chemical precursors currently sourced from the petrochemical industry.
Lignin, being a polyaromatic network has been extensively investigated as a suitable substitute for phenol during production of phenol-formaldehyde adhesives. These are used during manufacturing of laminate and structural wood products such as plywood, oriented strand board and fiberboard. During synthesis of such adhesives, phenol, which may be partially replaced by lignin, is reacted with formaldehyde in the presence of either basic or acidic catalyst to form a highly cross-linked aromatic resins termed novolacs (when utilizing acidic catalysts) or resoles (when utilizing basic catalysts). Currently, only limited amounts of the phenol can be replaced by lignin due to the lower reactivity of lignin.
One problem when preparing resins comprising lignin is the use of formaldehyde, when the lignin is used in formaldehyde-containing resins, such as Iignin-phenol-formaldehyde resins. Formaldehyde based resins emit formaldehyde, which is a toxic volatile organic compound. The present and proposed legislation directed to the lowering or elimination of formaldehyde emissions have led to the development of formaldehyde free resin for wood adhesive applications.
Jingxian Li R. et al. (Green Chemistry, 2018, 20, 1459-1466) describes preparation of a resin comprising glycerol diglycidyl ether and lignin, wherein the lignin is provided in solid form. One problem with the technology described in the article is a long pressing time and high pressing temperature. The 3 plies plywood sample was pressed at 150°C temperature forminutes to fully cure the resins.
Engelmann G. and Ganster J. (Holzforschung, 2014, 68, 435-446) describes preparation of a biobased epoxy resin with low molecular weight kraft lignin and pyrogallol, wherein the lignin component consists of an acetone extraction from Kraft lignin.
Summary of the invention lt has now surprisingly been found that it is possible to easily prepare a bonding resin in which the use of formaldehyde can be avoided. lt has also been found that an improved bonding resin can be achieved by providing lignin in the form of an aqueous solution comprising ammonia and/or an organic base. By providing the lignin in the form of an aqueous solution comprising ammonia and/or an organic base, the step of milling of lignin particles can be avoided, avoiding lignin lump formation and the use of dispersing agent. lt has been found that when lignin is provided in form of an aqueous solution comprising ammonia and/or organic base, the phenolic hydroxyl groups in the lignin structure are deprotonated and free to react with the epoxide groups. This improves the reactivity and performance of the binder. Therefore, providing the lignin in the form of a an aqueous solution comprising ammonia and/or an organic base speeds up the reaction significantly and hence reduces the pressing time and enables the use of a lower pressing temperature for curing the bonding resin, when manufacturing for example laminates, mineral wool insulation and wood products such as plywood, oriented strandboard (OSB), laminated veneer lumber (LVL), medium density fiberboards (MDF), high density fiberboards (HDF), parquet flooring, curved plywood, veneered particleboards, veneered MDF or particle boards. The bonding resin is also useful for example in composites, molding compounds and foundry applications.
Furthermore, by providing lignin in the form an aqueous solution of lignin comprising ammonia and/or an organic base the risk of degrading for example glass wool and mineral wool fibers is minimized.
The present invention is thus directed to a method for preparing a bonding resin, wherein an aqueous solution of lignin comprising ammonia and/or an organic base is mixed with one or more crosslinker selected from polyglycerol diglycidyl ether, polyglycerol polyglycidyl ether, glycerol triglycidyl ether, alkoxylated glycerol polyglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolpropane diglycidyl ether, polyoxypropylene glycol triglycidyl ether, diglycidylether of cyclohexane dimethanol, resorcinol diglycidyl ether, isosorbide diglycidyl ether or pentaerythritol tetraglycidyl ether.
One aspect of the present invention is a method for preparing a bonding resin, wherein an aqueous solution of lignin comprising ammonia and/or an organic base is mixed with one or more cross-linkers and/or one or more glycidyl ethers, wherein the cross-linker has an epoxy index above 4 eq/kg. The epoxy index can be determined according to ISO 3001. Preferably, the cross-linker has an epoxy index above 5 eq/kg. The cross-linker is an aliphatic or, preferably, aromatic glycidyl ether. Preferably, the cross-linker is aliphatic.
The glycidyl ethers may be polyfunctional epoxides and the method according to the present invention may use a mixture of epoxides, such as monofunctional, di-functional, tri-functional and/or tetra-functional.
The present invention is thus also directed to the use of the bonding resin in the manufacture of laminates, mineral wool insulation and wood products such as plywood, oriented strandboard (OSB), laminated veneer lumber (LVL), medium density fiberboards (MDF), high density fiberboards (HDF), parquet flooring, curved plywood, veneered particleboards, veneered MDF or particle boards. The bonding resin according to the present invention may also be used in the manufacture of composites, molding compounds and foundry applications.
Detailed description lt is intended throughout the present description that the expression "lignin" embraces any kind of lignin, e.g. lignin originated from hardwood, softwood or annular plants. The lignin is an alkaline lignin generated in e.g. the Kraft process. The lignin has been purified or isolated before being used in the process according to the present invention. The lignin may be isolated from black liquor and optionaily be further purified before being used in the process according to the present invention. The purification is typically such that the purity of the lignin is at least 90%, preferably at least 95%. Thus, the lignin used according to the method of the present invention preferably contains less than 10%, preferably less than 5% impurities. The lignin may then be separated from the black liquor by using the process disciosed in WO2006031175. The lignin may then be separated from the black liquor by using the process referred to as the LignoBoost process. The lignin may be provided in the form of particles, such as particles having an average particle size of from 50 micrometers to 500 micrometers.
The polyglycerol diglycidyl ether, polyglycerol polyglycidyl ether, glycerol triglycidyl ether, alkoxylated glycerol polyglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolpropane diglycidyl ether, polyoxypropylene glycol triglycidyl ether, diglycidylether of cyclohexane dimethanol, resorcinol diglycidyl ether, isosorbide diglycidyl ether or pentaerythritol tetraglycidyl ether used according to the present invention acts as a cross-linker. Glycidyl ethers with more functional epoxide groups can be used such as glycerol triglycidyl ether. As the chain lengths between two glycidyl ether groups gets longer, the resin becomes more flexible, which may negatively influence its performance. lt results in an adhesive during curing. Typically, the bonding resin according to the present invention is and applied to the surfaces of for example veneers, such as in the manufacture of plywood. When the veneers are pressed together under heating, the cross-linking in the bonding resin takes place, resulting in an adhesive.
An aqueous solution of lignin comprising ammonia and/or an organic base can be prepared by methods known in the art, such as by mixing lignin and ammonia and/or organic base with water. The pH of the aqueous solution of lignin comprising ammonia and/or an organic base is preferably in the range of from 10 to 14. Examples of organic bases include amines, such as primary, secondary and tertiary amines and mixtures thereof. Preferably, the organic base is selected from the group consisting of methylamine, ethylamine, propylamine, butylamine, ethylenediamine, methanolamine, ethanolamine, aniline, cyclohexylamine, benzylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, dimethanolamine, diethanolamine, diphenylamine, phenylmethylamine, phenylethylamine, dicyclohexylamine, piperazine, imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4- methylimidazole, 2-isopropylimidazole, 2- phenylimidazole, 2- methylimidazoline, 2-phenylimidazoline, trimethylamine, triethylamine, dimethylhexylamine, N-methylpiperazine, dimethylbenzylamine, aminomethyl propanol, tris(dimethy|aminomethyl)pheno| and dimethylaniline or mixtures thereof. The total amount of ammonia and/or organic base in the aqueous solution is preferably in the range of from 0.1 wt-% to 20 wt-%, preferably 0.1 wt-% to 10 wt-%, of the total weight of the aqueous solution comprising water, lignin and ammonia and/or an organic base. The amount of lignin in the aqueous solution of lignin comprising ammonia and/or an organic base is preferably from 1 wt-% to 60 wt-% of the solution, such as from 10 wt-% to 30 wt-% of the solution. The aqueous solution of lignin comprising ammonia and/or an organic base does not comprise alkali.
The weight ratio between lignin (dry weight) and the total amount of crosslinker is preferably in the range of from 1:10 to 10:1. The amount of lignin in the bonding resin is preferably from 5 wt-% to 50 wt-%, calculated as the dry weight of lignin and the total weight of the bonding resin.
The bonding resin may also comprise additives, such as urea, tannin, surfactants, dispersing agents and fillers.
The amount of urea in the bonding resin can be 0-40% preferably 5-20% calculated as the dry weight of urea and the total weight of the bonding resin.
A filler and/or hardener can also be added to the bonding resin. Examples of such fillers and/or hardeners include limestone, cellulose, sodium carbonate, and starch.
The reactivity of the Iignin with the glycidyl ether can be increased by modifying the Iignin by glyoxylation, etherification or esterification.
The aqueous solution of Iignin comprising ammonia and/or an organic base is preferably mixed with the glycidyl ether at room temperature, such as at a temperature of from 15°C to 30°C. The mixing is preferably carried out for about 5 seconds to 2 hours. Preferably, the viscosity of the mixture is monitored during mixing, either continuously or by taking samples and determining the viscosity thereof. ln the production of mineral wool insulation, curing of the bonding resin to form an adhesive takes place when the components used for the preparation of the mineral wool insulation are exposed to heating.
Examples ExampleLignin solution was prepared first by adding 243 g of powder Iignin (solid content 95%) and 619 g of waterwere added to a 1 L glass reactor at ambient temperature and were stirred until the Iignin was fully and evenly dispersed. Then, 138 g of 28-30% ammonia solution was added to the Iignin dispersion. The composition was stirred for 60 minutes to make sure that the Iignin was completely dissolved.
Example 2 3-Aminopropyl trimethoxysilane was diluted to 1% solution in water. Binder composition was prepared by weighing 31.2 g of Iignin-ammonia solution from the example 1, 7.8 g of polyglycerol polyglycidyl ether and 3 g of 1% of 3- Aminopropyl trimethoxysilane into a 250m| plastic container and was stirred with a wooden stick for 2 minutes. Silica sand was weighed into a bowl and the lignin mixture were poured on top of the sand and mixed with an electric hand mixer for 2 minutes. Then, the sand bars were prepared by putting the sand-binder mixture into a mould for baking in an oven at 200°C for 2 hours. All sand bars were hard and stable after curing in the oven. The size of the bar for each test is height x thickness x length: 23mm x 22mm x 84mm.
Sand bars were conditioned in a water bath at 80°C for 2 hours. Sand bars were post-cured for 24 hours and soaked in a water bath at 80°C for 2 hours. The sand bars were evaluated with 3 point bending test. The flexural strength before and after water soaking is given in the Table ExampleBinder composition was prepared by weighing 37.8 g of lignin-ammonia solution from the example 1, 7.6 g of polyglycerol polyglycidyl ether and 3 g of 1% of 3-aminopropyl trimethoxysilane into a 250ml plastic container and was stirred with a wooden stick for 2 minutes. Silica sand was weighed in to a bowl and the lignin mixture were poured on top of the sand and mixed with an electric hand mixer for 2 minutes. Then, the sand bars were prepared by putting the sand-binder mixture into a mould for baking in an oven at 180°C for 2 hours. All sand bars were hard and stable after curing in the oven.
Sand bars were conditioned in a water bath at 80°C for 2 hours. Sand bars were post-cured for 24 hours and then soaked in a water bath at 80°C for 2 hours. The sand bars were evaluated with 3 point bending test. The flexural strength before and after water soaking is given in the Table Flexural Strength Flexural Strength after without conditioning conditioning [MPa] [MPa] Sand bars from the 8.8 3.ExampleSand bars from the 7.1 2.5 ExampleTable 1. Flexural Strength of the sand bars with and without Conditioning ln view of the above detailed description of the present invention, other modifications and Variations will become apparent to those skilled in the art.
However, it should be apparent that such other modifications and Variations may be effected without departing from the spirit and scope of the invention.
Claims (1)
1.Claims A method for preparing a bonding resin, wherein an aqueous solution of lignin comprising ammonia and/or an organic base is mixed with one or more crosslinker selected from polyglycerol diglycidyl ether, polyglycerol polyglycidyl ether, glycerol triglycidyl ether, alkoxylated glycerol polyglycidyl ether, trimethylolpropane triglycidyl ether, trimethylolpropane diglycidyl ether, polyoxypropylene glycol triglycidyl ether, diglycidylether of cyclohexane dimethanol, resorcinol diglycidyl ether, isosorbide diglycidyl ether or pentaerythritol tetraglycidyl ether, and optionally one or more additives; wherein the lignin has been generated in the Kraft process and is optionally modified by glyoxylation, etherification or esterification. A method according to claim 1, wherein the crosslinker is polyglycerol polyglycidyl ether. A method according to claim 1 or 2, wherein the aqueous solution of lignin comprising ammonia and/or an organic base comprises at least 5% by weight of lignin. A method according to any one of claims 1-3, wherein the weight ratio between lignin, calculated on the basis of dry lignin, and the total amount of crosslinker is from 1:10 to 10: A method according to any one of claims 1-4, wherein the additive is urea, tannin, surfactant, dispersing agent, and/or a filler. A method according to any one of claims 1-5, wherein the lignin is modified by glyoxylation, etherification, esterification. Use of a bonding resin prepared according to any one of claims 1-6 in the manufacture of a laminate, mineral wool insulation, wood product such as plywood, oriented strandboard (OSB), laminated veneer lumber (LVL), medium density fiberboards (MDF), high density fiberboards (HDF), parquet flooring, curvedplywood, veneered particleboards, veneered MDF or particle boards. Use of a bonding resin according to claim 7, wherein the bonding resin is provided to a surface in the preparation of a laminate, mineral wool insulation, wood product such as plywood, oriented strandboard (OSB), laminated veneer lumber (LVL), medium density fiberboards (MDF), high density fiberboards (HDF), parquet flooring, curved plywood, veneered particleboards, veneered MDF or particle boards, and wherein curing of the bonding resin to form an adhesive takes place when the surface is exposed to pressure and heating.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1951516A SE545325C2 (en) | 2019-12-20 | 2019-12-20 | Process for the preparation of a bonding resin |
| BR112022011952A BR112022011952A2 (en) | 2019-12-20 | 2020-12-16 | PROCESS FOR THE PREPARATION OF A BINDING RESIN |
| AU2020407553A AU2020407553A1 (en) | 2019-12-20 | 2020-12-16 | Process for the preparation of a bonding resin |
| CN202080088692.3A CN114867809A (en) | 2019-12-20 | 2020-12-16 | Process for preparing adhesive resins |
| EP20900973.7A EP4077578A4 (en) | 2019-12-20 | 2020-12-16 | Process for the preparation of a bonding resin |
| CA3165411A CA3165411A1 (en) | 2019-12-20 | 2020-12-16 | Process for the preparation of a bonding resin |
| US17/757,258 US20230002654A1 (en) | 2019-12-20 | 2020-12-16 | Process for the preparation of a bonding resin |
| JP2022536561A JP2023506815A (en) | 2019-12-20 | 2020-12-16 | Method for preparing bonding resin |
| PCT/IB2020/061996 WO2021124125A1 (en) | 2019-12-20 | 2020-12-16 | Process for the preparation of a bonding resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1951516A SE545325C2 (en) | 2019-12-20 | 2019-12-20 | Process for the preparation of a bonding resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE1951516A1 SE1951516A1 (en) | 2021-06-21 |
| SE545325C2 true SE545325C2 (en) | 2023-07-04 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE1951516A SE545325C2 (en) | 2019-12-20 | 2019-12-20 | Process for the preparation of a bonding resin |
Country Status (1)
| Country | Link |
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| SE (1) | SE545325C2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE545414C2 (en) * | 2021-12-21 | 2023-09-05 | Stora Enso Oyj | Process for the preparation of a bonding resin |
| SE545570C2 (en) * | 2021-12-21 | 2023-10-24 | Stora Enso Oyj | A bonding resin and a process for the preparation of a bonding resin |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2664377A (en) * | 1950-04-24 | 1953-12-29 | Weyerhaeuser Timber Co | Method of impregnating and laminating fibrous materials with lignin |
| JP2011116930A (en) * | 2009-10-27 | 2011-06-16 | Panasonic Electric Works Co Ltd | Vegetable-originated adhesive, vegetable originated composition, and wood composite material |
| US8268102B2 (en) * | 2002-05-13 | 2012-09-18 | State Of Oregon Acting By And Through The Oregon State Board Of Higher Education On Behalf Of Oregon State University | Formaldehyde-free lignocellulosic adhesives and composites made from the adhesives |
| US20150329753A1 (en) * | 2014-05-16 | 2015-11-19 | Board Of Trustees Of The Leland Stanford Junior University | Biobased lignin adhesives for plywood applications and manufacturing of improved wood-based products |
| US20160208134A1 (en) * | 2013-09-27 | 2016-07-21 | Stora Enso Oyj | A composition comprising lignin and epoxy compound for coating and method for the manufacturing thereof and use thereof |
| CN108192547A (en) * | 2017-12-29 | 2018-06-22 | 武汉市科达云石护理材料有限公司 | Height filling high tenacity epoxy stone adhesive and preparation method thereof |
| US20180355119A1 (en) * | 2012-12-18 | 2018-12-13 | Akzo Nobel Coatings International B.V. | Lignin Based Coating Compositions |
| EP3633005A1 (en) * | 2018-10-05 | 2020-04-08 | Aarhus Universitet | An aqueous adhesive composition for lignocellulosic materials such as wood and a method of production |
| EP3632866A1 (en) * | 2018-10-05 | 2020-04-08 | Rockwool International A/S | Aqueous binder composition |
-
2019
- 2019-12-20 SE SE1951516A patent/SE545325C2/en unknown
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2664377A (en) * | 1950-04-24 | 1953-12-29 | Weyerhaeuser Timber Co | Method of impregnating and laminating fibrous materials with lignin |
| US8268102B2 (en) * | 2002-05-13 | 2012-09-18 | State Of Oregon Acting By And Through The Oregon State Board Of Higher Education On Behalf Of Oregon State University | Formaldehyde-free lignocellulosic adhesives and composites made from the adhesives |
| JP2011116930A (en) * | 2009-10-27 | 2011-06-16 | Panasonic Electric Works Co Ltd | Vegetable-originated adhesive, vegetable originated composition, and wood composite material |
| US20180355119A1 (en) * | 2012-12-18 | 2018-12-13 | Akzo Nobel Coatings International B.V. | Lignin Based Coating Compositions |
| US20160208134A1 (en) * | 2013-09-27 | 2016-07-21 | Stora Enso Oyj | A composition comprising lignin and epoxy compound for coating and method for the manufacturing thereof and use thereof |
| US20150329753A1 (en) * | 2014-05-16 | 2015-11-19 | Board Of Trustees Of The Leland Stanford Junior University | Biobased lignin adhesives for plywood applications and manufacturing of improved wood-based products |
| CN108192547A (en) * | 2017-12-29 | 2018-06-22 | 武汉市科达云石护理材料有限公司 | Height filling high tenacity epoxy stone adhesive and preparation method thereof |
| EP3633005A1 (en) * | 2018-10-05 | 2020-04-08 | Aarhus Universitet | An aqueous adhesive composition for lignocellulosic materials such as wood and a method of production |
| EP3632866A1 (en) * | 2018-10-05 | 2020-04-08 | Rockwool International A/S | Aqueous binder composition |
| WO2020069984A1 (en) * | 2018-10-05 | 2020-04-09 | Aarhus Universitet | An aqueous adhesive composition for lignocellulosic materials such as wood and a method of production |
| WO2020070337A1 (en) * | 2018-10-05 | 2020-04-09 | Rockwool International A/S | Aqueous binder composition |
Non-Patent Citations (2)
| Title |
|---|
| LI, R. J., ET AL. "A lignin-epoxy resin derived from biomass as an alternative to formaldehyde-based wood adhesives", Green Chemistry, 2018, Vol. 20, pp. 1459-1466 * |
| NONAKA, Y., ET AL. "Synthesis of lignin/epoxy resins in aqueous systems and their properties", Holzforschung, 1997, Vol. 51, No. 2, pp. 183-187 * |
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| SE1951516A1 (en) | 2021-06-21 |
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