SE546098C2 - Method for preparing a bonding resin comprising lignin, a bonding resin comprising lignin, products comprising said bonding resin, and use of said bonding resin - Google Patents
Method for preparing a bonding resin comprising lignin, a bonding resin comprising lignin, products comprising said bonding resin, and use of said bonding resinInfo
- Publication number
- SE546098C2 SE546098C2 SE2050835A SE2050835A SE546098C2 SE 546098 C2 SE546098 C2 SE 546098C2 SE 2050835 A SE2050835 A SE 2050835A SE 2050835 A SE2050835 A SE 2050835A SE 546098 C2 SE546098 C2 SE 546098C2
- Authority
- SE
- Sweden
- Prior art keywords
- lignin
- bonding resin
- crosslinker
- products
- functional group
- Prior art date
Links
- 229920005610 lignin Polymers 0.000 title claims abstract description 82
- 229920005989 resin Polymers 0.000 title claims abstract description 58
- 239000011347 resin Substances 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000004971 Cross linker Substances 0.000 claims abstract description 21
- 239000000843 powder Substances 0.000 claims abstract description 17
- 239000006185 dispersion Substances 0.000 claims abstract description 13
- 150000001412 amines Chemical class 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 239000000654 additive Substances 0.000 claims abstract description 9
- 150000001408 amides Chemical class 0.000 claims abstract description 8
- 150000003949 imides Chemical class 0.000 claims abstract description 8
- 150000002466 imines Chemical class 0.000 claims abstract description 8
- 125000000524 functional group Chemical group 0.000 claims abstract description 7
- 229920000962 poly(amidoamine) Polymers 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 239000011120 plywood Substances 0.000 claims description 9
- 239000002023 wood Substances 0.000 claims description 9
- 239000000853 adhesive Substances 0.000 claims description 8
- 230000001070 adhesive effect Effects 0.000 claims description 8
- 239000011094 fiberboard Substances 0.000 claims description 7
- 238000009408 flooring Methods 0.000 claims description 7
- 239000011491 glass wool Substances 0.000 claims description 7
- 239000011490 mineral wool Substances 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 238000009413 insulation Methods 0.000 claims description 5
- 239000002655 kraft paper Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 4
- 238000006266 etherification reaction Methods 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 239000004848 polyfunctional curative Substances 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002009 diols Chemical group 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 239000001648 tannin Substances 0.000 claims description 2
- 235000018553 tannin Nutrition 0.000 claims description 2
- 229920001864 tannin Polymers 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000002156 mixing Methods 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000004033 plastic Substances 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 230000003750 conditioning effect Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 239000003637 basic solution Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012707 chemical precursor Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- HANVTCGOAROXMV-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine;urea Chemical compound O=C.NC(N)=O.NC1=NC(N)=NC(N)=N1 HANVTCGOAROXMV-UHFFFAOYSA-N 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000011121 hardwood Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000007731 hot pressing Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- B27N3/002—Manufacture of substantially flat articles, e.g. boards, from particles or fibres characterised by the type of binder
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
-
- 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
- B27N3/02—Manufacture of substantially flat articles, e.g. boards, from particles or fibres from particles
-
- 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
- B27N3/04—Manufacture of substantially flat articles, e.g. boards, from particles or fibres from fibres
-
- 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
- B27N3/08—Moulding or pressing
-
- 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
- B27N5/00—Manufacture of non-flat articles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Manufacturing & Machinery (AREA)
- Wood Science & Technology (AREA)
- Forests & Forestry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The present invention is directed to a method for preparing a bonding resin, wherein lignin in powder form or in the form of an aqueous dispersion is mixed with at an aqueous solution of least one substantially formaldehydefree crosslinker that includes at least one amine, amide, imine, imide, or nitrogen-containing heterocyclic functional group that can react with at least one functional group of the lignin, at a pH in the range of from 3 to 9, and optionally one or more additives.
Description
Field of the invention
The present invention relates to a method for preparing a bonding resin useful for example in the manufacture of mineral wool insu|ation products, glass wool products, laminates, boards and wood products such as particleboards, medium density fibreboards (MDF), high density fiberboards, flooring and plywood.
Background
For mineral wool insu|ation products, glass wool products, laminates, boards such as corrugated boards, and wood products such as particleboards, medium density fibreboards (MDF), high density fiberboards, flooring and plywood, currently used resins are typically formaldehyde-based resins such as urea formaldehyde, melamine-urea-formaldehyde, phenol-urea-formaldehyde and 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. Lignin, being green and renewable material, is suitable for replacement of hazardous and fossil-based chemicals in the resins.
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.
US2007218307 describes a method using an adhesive composition wherein lignin was dissolved in an alkali solution and was reacted with a formaldehyde free curing agent based on a compound that includes at least one amine, amide, imine, imide or nitrogen-containing heterocyclic functional group, e.g. polyamidoamine epichlorohydrin. However, the binder does not give enough wet strength to pass the standard test requirements.
Summary of the invention
lt has now been found that the wet strength of an adhesive obtained from a bonding resin comprising lignin can be improved.
lt has surprisingly been found that when lignin powder or lignin in the form of an aqueous dispersion is mixed with an aqueous solution of at least one substantially formaldehyde-free crosslinker that includes at least one amine, amide, imine, imide, or nitrogen-containing heterocyclic functional group that can react with at least one functional group of the lignin, at a pH in the range of from 3 to 9, and optionally one or more additives, a bonding resin that leads to an adhesive with very good bonding strength (wet strength) and
moisture resistance is obtained.
When lignin in the form of a powder or in the form of an aqueous dispersion is mixed with an aqueous solution of at least one substantially formaldehyde- free crosslinker that includes at least one amine, amide, imine, imide, or
nitrogen-containing heterocyclic functional group that can react with at least
one functional group of the lignin, at a pH in the range of from 3 to 9, the lignin becomes at least partly dissolved. ln addition, the phenolic hydroxyl groups in the lignin structure are deprotonated and free to react with the crosslinker. This catalyzes the reaction and improves the reactivity and performance of the binder. Therefore, it is possible to easily prepare a bonding resin in which the use of formaldehyde can be avoided, i.e. which is free from formaldehyde.
The present invention is thus directed to a method for preparing a bonding resin, wherein lignin in powderform or in the form of an aqueous dispersion is mixed with an aqueous solution of at least one substantially formaldehyde- free crosslinker that includes at least one amine, amide, imine, imide, or nitrogen-containing heterocyclic functional group that can react with at least one functional group of the lignin, at a pH in the range of from 3 to 9, and optionally one or more additives, wherein the lignin is an alkaline lignin generated in the Kraft process and wherein the lignin is optionally modified by
glyoxylation, etherification or esterification.
The present invention is also directed to a bonding resin comprising lignin in solid form, such as lignin powder, and at least one substantially formaldehyde-free crosslinker that includes at least one amine, amide, imine, imide, or nitrogen-containing heterocyclic functional group that can react with at least one functional group of the lignin, having a pH in the range of from 3 to 9 and wherein the lignin is an alkaline lignin generated in the Kraft process and wherein the lignin is optionally modified by glyoxylation, etherification or esterification and to the use of the bonding resin in the manufacture of mineral wool insulation products, glass wool products, laminates, boards such as corrugated boards, or wood products such as particleboards, medium density fibreboards (MDF), high density fiberboards, flooring or plywood. The present invention is also directed to such mineral wool insulation products, glass wool products, laminates, boards such as corrugated boards, and wood products such as particleboards, medium density fibreboards (MDF), high
density fiberboards, flooring or plywood manufactured using the bonding
resin.
Detailed description
lt is intended throughout the present description that the expression "|ignin" 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. Preferably, 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 Iiquor and optionally 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%, more preferably at least 98%. Thus, the lignin used according to the method of the present invention preferably contains less than 10%, preferably less than 5% or less than less than 2% impurities. The lignin may then be separated from the black Iiquor by using the process disclosed in WO2006031175. The lignin may then be separated from the black Iiquor by using the process referred to
as the LignoBoost process.
The particle size of the lignin powder is preferably such that 50 wt-% of the particles have a particle size larger than 100 micrometers. Preferably, at least 20 wt-% of the particles have a particle size larger than 300 micrometers. Typically, at least 80 wt-% of the agglomerates have a diameter within the range of from 0.2 mm to 5.0 mm, more preferably at least 80 wt-% of the agglomerates have a diameter within the range of from 0.2 mm to 2.0 mm. Preferably, at least 80 wt-% of the particles have a particle size smaller than 2000 micrometers. Preferably, the moisture content of the particles is less
than 40 wt-%, more preferably less than 20 wt-%.
The crosslinker is for example adducts of epoxides with polyamine resins, polyamidoamines resins, or polyamide resins. Preferably, the crosslinker is
polyamidoamine epichlorohydrin, polyvinyl amine or a combination thereof.
The crosslinker is provided as an aqueous solution. The concentration of the crosslinker is typically 10-20%. When mixed with the lignin in the form of a powder or in the form of an aqueous dispersion, an adhesive is obtained. The forming of the adhesive is often referred to as curing. Typically, the bonding resin according to the present invention is applied to a surface, such as 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.
When the lignin powder or lignin in the form of an aqueous dispersion is mixed with the crosslinker, the pH of the mixture is in the range of from 3 to 9, preferably in the range of from 4 to 9, more preferably in the range of from 6 to
The lignin in the form of an aqueous dispersion can be prepared by mixing lignin, preferably lignin powder, with water, to obtain a dispersion. Preferably, the pH of the aqueous medium with which the lignin is mixed is in the range of from 5 to 9, such as from 5 to 7 or from 5 to 8 or from 6 to 8. The pH of the aqueous medium and/or the aqueous dispersion can be adjusted by adding
acid or base. For example, a basic solution can be added to increase the pH.
The pH of the basic solution is preferably in the range of from 10 to 14. Examples of suitable bases include sodium hydroxide, potassium hydroxide, ammonia or other organic base, and mixtures thereof. ln one embodiment, the amount of alkali in the basic solution is preferably from 0.1 wt-% to 60 wt- % of the solution, such as from 20 wt-% to 55 wt-% of the solution. ln one embodiment, the basic solution is aqueous.
lf the bonding resin comprises additives, the additives can for example be urea, tannin, solvents, surfactants, tensides, dispersing agents, fillers and hardeners. 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 Iimestone, cellulose, sodium carbonate, and starch. Solvents that can be used as additives in the bonding resins according to the present invention are for example glycerol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, sorbitol and/or any terminal diol having a linear carbon chain of 3-6 carbon
atoms.
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 reactivity of the lignin with the crosslinker can be increased by modifying
the lignin by glyoxylation, etherificationor esterification.
The lignin in powder form or in the form of an aqueous dispersion is preferably mixed with the crosslinker (as an aqueous solution), at room temperature, such as at a temperature of from 15°C to 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 samples and determining the viscosity thereof. The mixing can also be carried out by providing the crosslinker as an aqueous solution, on lignin particles, such as by spraying the crosslinker as an aqueous solution onto lignin
particles, optionally followed by drying.
Examples
Example 1 (comparative)
Lignin solution was prepared first by adding 180 g of powder lignin (solid content 90%) and 260 g of water were added to a 1 L glass reactor at ambient temperature and were stirred until the lignin was fully and evenly dispersed. Then, 60 g of 50% alkali solution was added to the lignin dispersion. The composition was stirred for 120 minutes to make sure that the lignin was completely dissolved in the alkaline media.
An bonding resin was prepared by mixing g of 82g of the lignin solution and 19 g of 16% polyamidoamine epichlorohydrin (PAE) solution using an overhead stirrer at room temperature in a 250 ml plastic beaker for 30 minutes or until the mixture is evenly dispersed. The pH of the formulation
was 11.
The bonding resin was tested in a lap-joint test using an Automated Bonding Evaluation System (ABES) tensile tester.
For this purpose, relatively thin beech veneers of thickness of 0.6 mm were used that were cut into 105x20 mm pieces. Resin was applied to an area of 5 mm x 20 mm on one side of one end section of the two pieces. Resin coated, overlapped end section of a series of specimens were pressed together in a hot press at a pressure of 5 kg/m2 using pressing time of 90 seconds at
pressing temperature of 150 °C.
Prior to evaluation, few samples were soaked in water for 24 hours at room temperature. Average data from five test specimens with and without conditioning is presented in the Table 1. All the samples delaminated after
water soaking.
Shear strength [N/mmz] Dry Strength
Shear strength [N/mmz] Wet Strength
Bonding resin 2.0Table 1: Dry and wet shear strength
Example 2 (comparative)
Lignin solution was prepared first by adding 161 g of powder lignin (solid content 90%) and 320 g of water were added to a 1 L glass reactor at ambient temperature and were stirred until the lignin was fully and evenly dispersed. Then, 35 g of 50% alkali solution was added to the lignin dispersion. The composition was stirred for 120 minutes to make sure that the lignin was completely dissolved in the alkaline media.
A bonding resin was prepared by mixing g of 82g of the lignin solution and 22 g of 16% polyamidoamine epichlorohydrin (PAE) solution using an overhead stirrer at room temperature in a 250 ml plastic beaker for 30 minutes or until
the mixture is evenly dispersed. The pH of the formulation was 10.
The bonding resin was tested in a lap-joint test using an Automated Bonding Evaluation System (ABES) tensile tester as described by the procedure in the
example
Average data from five test specimens with and without conditioning is presented in the Table 2. All the samples were delaminated.
Shear strength [N/mmz] Shear strength [N/mm2] Dry Strength Wet Strength
Bonding resin 1.8Table 2: Dry and wet shear strength
Example 3 A bonding resin was prepared by mixing 28 g of powder lignin (solid content
90%), 1.55g of 50% sodium hydroxide solution, 38g of 16% polyamidoamine epichlorohydrin (PAE) solution and 21 g of 15% polyvinyl alcohol using an overhead stirrer at room temperature in a 250 ml plastic beaker for 30 minutes or until the mixture is evenly dispersed. The pH of the formulation
was 6.
The bonding resin was tested in a lap-joint test using an Automated Bonding Evaluation System (ABES) tensile tester as described by the procedure in the
example
Average data from five test specimens with and without conditioning is presented in the Table
Shear strength [N/mm2] Dry Strength
Shear strength [N/mmz] Wet Strength
Bonding resin 4-6 2.Table 3: Dry and wet shear strength
ExamgleA bonding resin was prepared by mixing 34 g of powder lignin (solid content 90%), 1.8 g of 50% sodium hydroxide solution, 44 g of 16% polyamidoamine epichlorohydrin (PAE) solution and 19 g of glycerol using an overhead stirrer at room temperature in a 250 ml plastic beaker for 30 minutes or until the
mixture is evenly dispersed. The pH of the formulation was 6.
The bonding resin was tested in a lap-joint test using an Automated Bonding Evaluation System (ABES) tensile tester as described by the procedure in the
example
Average data from five test specimens with and without conditioning is presented in the Table
Shear strength [N/mmz] Dry Strength
Shear strength [N/mmz] Wet Strength
Bonding resin 4-2 2.Table 4: Dry and wet shear strength
ExamgleA bonding resin was prepared by mixing 44 g of powder lignin (solid content 90%), 2.6 g of 50% sodium hydroxide solution, 17g of water, 44 g of 16% polyamidoamine epichlorohydrin (PAE) solution and 34 g of 15% polyvinyl alcohol solution using an overhead stirrer at room temperature in a 250 ml
plastic beaker for 30 minutes or until the mixture is evenly dispersed.
The bonding resin was used to prepare a 5-ply plywood panel. Birch veneers of thickness 1.54-1.62 mm were sawn to 300 x 300 mm2 size and conditioned in 20°C, 65% RH prior to manufacture. Target glue content was 220 g/m2 which were spread on one side. Hot pressing was performed at 150°C with a pressure of 1.8 MPa for 9 minutes.
Shear strength of the test pieces were evaluated according to EN314_1_2005 test method. Prior to evaluation, samples were conditioned for class 1 (dry interior) according to 5.1.1 in the EN314_1_2005. Average data from 20 test specimens is presented in Table
Shear strength [N/mm2]
Bonding resin 1.Table 5: Shear strength of test specimen according to EN314_1_Examgle 5 A bonding resin was prepared by mixing 36 g of powder lignin (solid content
90%), 47.4 g of water and 23 g of 18% polyvinyl amine solution using an overhead stirrer at room temperature in a 250 ml plastic beaker for 30 minutes or until the mixture is evenly dispersed. The pH of the formulation was 4.
The bonding resin was tested in a lap-joint test using an Automated Bonding Evaluation System (ABES) tensile tester as described by the procedure in
exampleAverage data from five test specimens with and without Conditioning is
presented in the Table
Shear strength [N/mm2] Dry Strength
Shear strength [N/mmz] Wet Strength
Bonding resin
2.1.Table 6: Dry and wet shear strength
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)
- Claims A method for preparing a bonding resin, characterized by that lignin in powder form or in the form of an aqueous dispersion is mixed with an aqueous solution of at least one substantially formaldehyde-free crosslinker that includes at least one amine, amide, imine, imide, or nitrogen-containing heterocyclic functional group that can react with at least one functional group of the lignin, at a pH in the range of from 3 to 9, and optionally one or more additives, wherein the lignin is an alkaline lignin generated in the Kraft process and wherein the lignin is optionally modified by glyoxylation, etherification or esterification. A method according to claim 1, where the crosslinker is polyamidoamine epichlorohydrin, polyvinyl amine or a combination thereof. A method according to claim 1 or 2, 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 1-3, wherein one additive is urea, tannin, a surfactant, a dispersing agent, tenside, a filler, a hardener and/or a solvent. A method according to claim 4, wherein one additive is a solvent and the solvent is glycerol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, sorbitol and/or a terminal diol having a linear carbon chain of 3-6 carbon atoms. A bonding resin comprising lignin in solid form and at least one aqueous solution of at least one substantially formaldehyde-free crosslinker that includes at least one amine, amide, imine, imide, or nitrogen-containing heterocyclic functional group that can react with at least one functional group of the lignin, having a pH in the range of from 3 to 9 and wherein the lignin is an alkaline ligningenerated in the Kraft process and wherein the lignin is optionally modified by glyoxylation, etherification or esterification. A bonding resin according to claim 6, wherein the crosslinker is polyamidoamine epichlorohydrin, polyvinyl amine or a combination thereof. A bonding resin according to claim 6 or 7, wherein the lignin in solid form is lignin powder. Use of a bonding resin according to any one of claims 6-8 in the manufacture of mineral wool insulation products, glass wool products, lamínates, boards, corrugated boards, or wood products such as particleboards, medium density fibreboards (MDF), high density fiberboards, flooring and plywood. Use of a bonding resin according to any one of claims 6-8, wherein the bonding resin is provided to a surface in the preparation of mineral wool insulation products, glass wool products, lamínates, boards, corrugated boards, or wood products such as particleboards, medium density fibreboards (MDF), high density fiberboards, flooring and plywood, and wherein curing of the bonding resin to form an adhesive takes place when the surface is exposed to pressure and heating. Mineral wool insulation product, glass wool product, laminate, board, corrugated board, or wood product such as particleboards, medium density fibreboards (MDF), high density fiberboards, flooring and plywood manufactured using a bonding resin according to any one of claims 6-8.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE2050835A SE546098C2 (en) | 2020-07-03 | 2020-07-03 | Method for preparing a bonding resin comprising lignin, a bonding resin comprising lignin, products comprising said bonding resin, and use of said bonding resin |
| EP21832758.3A EP4176018A4 (en) | 2020-07-03 | 2021-07-01 | METHOD FOR PREPARING A BONDING RESIN |
| PCT/IB2021/055902 WO2022003614A1 (en) | 2020-07-03 | 2021-07-01 | Method for preparing a bonding resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE2050835A SE546098C2 (en) | 2020-07-03 | 2020-07-03 | Method for preparing a bonding resin comprising lignin, a bonding resin comprising lignin, products comprising said bonding resin, and use of said bonding resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE2050835A1 SE2050835A1 (en) | 2022-01-04 |
| SE546098C2 true SE546098C2 (en) | 2024-05-21 |
Family
ID=79315662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE2050835A SE546098C2 (en) | 2020-07-03 | 2020-07-03 | Method for preparing a bonding resin comprising lignin, a bonding resin comprising lignin, products comprising said bonding resin, and use of said bonding resin |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP4176018A4 (en) |
| SE (1) | SE546098C2 (en) |
| WO (1) | WO2022003614A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4484515A1 (en) | 2023-06-27 | 2025-01-01 | SWISS KRONO Tec AG | Sugar-containing binder composition for wood-based boards, in particular chip boards, as a one-component system |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1778857A (en) * | 2004-11-26 | 2006-05-31 | 江西南大中德食品工程中心 | Biomass-base artifical plate wooden adhesive without formaldehyde indoor and production thereof |
| US20070218307A1 (en) * | 2002-05-13 | 2007-09-20 | State Of Oregon Acting By And Through The Oregon State Board Of Higher Education On Behalf Of Orego | Formaldehyde-free lignocellulosic adhesives and composites made from the adhesives |
| WO2008118741A1 (en) * | 2007-03-23 | 2008-10-02 | Hercules Inc. | Adhesive, formulations containing urea additives, methods of forming plywood therewith, and plywood products made thereby |
| US20110159768A1 (en) * | 2009-12-30 | 2011-06-30 | Crescimanno Stephen A | Carboxylated lignin based binders |
| WO2016009054A1 (en) * | 2014-07-17 | 2016-01-21 | Knauf Insulation Sprl | Improved Binder Compositions and Uses Thereof |
| CN105397898A (en) * | 2015-11-24 | 2016-03-16 | 中南林业科技大学 | Preparation method for artificial board without artificial formaldehyde release |
| EP3266810A1 (en) * | 2016-07-05 | 2018-01-10 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Lignin based composite material and method for its production |
| US20200040022A1 (en) * | 2013-11-26 | 2020-02-06 | Upm-Kymmene Corporation | Method for treating lignin and for producing a binder composition |
| CN111216212A (en) * | 2020-03-10 | 2020-06-02 | 杨晨露 | Bamboo-wood fiberboard using bio-based formaldehyde-free glue and preparation method thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110409218A (en) * | 2018-04-27 | 2019-11-05 | 上海东升新材料有限公司 | A kind of lignin modification emulsifier and the AKD lotion using emulsifier preparation |
-
2020
- 2020-07-03 SE SE2050835A patent/SE546098C2/en unknown
-
2021
- 2021-07-01 WO PCT/IB2021/055902 patent/WO2022003614A1/en active Application Filing
- 2021-07-01 EP EP21832758.3A patent/EP4176018A4/en active Pending
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070218307A1 (en) * | 2002-05-13 | 2007-09-20 | State Of Oregon Acting By And Through The Oregon State Board Of Higher Education On Behalf Of Orego | Formaldehyde-free lignocellulosic adhesives and composites made from the adhesives |
| CN1778857A (en) * | 2004-11-26 | 2006-05-31 | 江西南大中德食品工程中心 | Biomass-base artifical plate wooden adhesive without formaldehyde indoor and production thereof |
| WO2008118741A1 (en) * | 2007-03-23 | 2008-10-02 | Hercules Inc. | Adhesive, formulations containing urea additives, methods of forming plywood therewith, and plywood products made thereby |
| US20110159768A1 (en) * | 2009-12-30 | 2011-06-30 | Crescimanno Stephen A | Carboxylated lignin based binders |
| US20200040022A1 (en) * | 2013-11-26 | 2020-02-06 | Upm-Kymmene Corporation | Method for treating lignin and for producing a binder composition |
| WO2016009054A1 (en) * | 2014-07-17 | 2016-01-21 | Knauf Insulation Sprl | Improved Binder Compositions and Uses Thereof |
| CN105397898A (en) * | 2015-11-24 | 2016-03-16 | 中南林业科技大学 | Preparation method for artificial board without artificial formaldehyde release |
| EP3266810A1 (en) * | 2016-07-05 | 2018-01-10 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Lignin based composite material and method for its production |
| CN111216212A (en) * | 2020-03-10 | 2020-06-02 | 杨晨露 | Bamboo-wood fiberboard using bio-based formaldehyde-free glue and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| GENG, X. et al. "Investigation of wood adhesives from kraft lignin and polyethylenimine" In: Journal of Adhesion Science and Technology, 2006, Vol. 20, No. 8, pp. 847-858, ISSN 0169-4243 * |
Also Published As
| Publication number | Publication date |
|---|---|
| SE2050835A1 (en) | 2022-01-04 |
| EP4176018A1 (en) | 2023-05-10 |
| WO2022003614A1 (en) | 2022-01-06 |
| EP4176018A4 (en) | 2024-07-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US12163064B2 (en) | Process for preparing a bonding resin | |
| US11981838B2 (en) | Adhesive formulation comprising lignin | |
| KR101226062B1 (en) | Formaldehyde-free lignocellulosic adhesives and composites made from the adhesives | |
| US7252735B2 (en) | Formaldehyde-free lignocellulosic adhesives and composites made from the adhesives | |
| US12077682B2 (en) | Use of bonding resin | |
| CA3141289A1 (en) | Process for preparing a bonding resin | |
| EP4176018A1 (en) | Method for preparing a bonding resin | |
| SE545325C2 (en) | Process for the preparation of a bonding resin | |
| US20230026752A1 (en) | Novel process for preparing a bonding resin | |
| US20100233475A1 (en) | Multifunctional surface treatment |
