EP3781641A1 - Procédé de préparation d'une résine de collage - Google Patents

Procédé de préparation d'une résine de collage

Info

Publication number
EP3781641A1
EP3781641A1 EP19788281.4A EP19788281A EP3781641A1 EP 3781641 A1 EP3781641 A1 EP 3781641A1 EP 19788281 A EP19788281 A EP 19788281A EP 3781641 A1 EP3781641 A1 EP 3781641A1
Authority
EP
European Patent Office
Prior art keywords
resin
mixture
lignin
properties
preparing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19788281.4A
Other languages
German (de)
English (en)
Other versions
EP3781641A4 (fr
Inventor
Ben NASLI BAKIR
Ashar ZAFAR
Jesper EKSTRÖM
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Stora Enso Oyj
Original Assignee
Stora Enso Oyj
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Stora Enso Oyj filed Critical Stora Enso Oyj
Publication of EP3781641A1 publication Critical patent/EP3781641A1/fr
Publication of EP3781641A4 publication Critical patent/EP3781641A4/fr
Withdrawn legal-status Critical Current

Links

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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
    • C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
    • C08G16/0293—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with natural products, oils, bitumens, residues
    • 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
    • B27N1/00—Pretreatment of moulding material
    • B27N1/02—Mixing the material with binding agent
    • B27N1/0209—Methods, e.g. characterised by the composition of the agent
    • 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
    • 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
    • B27N3/007—Manufacture of substantially flat articles, e.g. boards, from particles or fibres and at least partly composed of recycled material
    • 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
    • C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
    • C08H8/00—Macromolecular compounds derived from lignocellulosic materials
    • 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
    • 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
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
    • 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
    • C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
    • C09J161/04—Condensation polymers of aldehydes or ketones with phenols only
    • C09J161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • 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
    • 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
    • C09J2461/00—Presence of condensation polymers of aldehydes or ketones
    • 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
    • C09J2497/00—Presence of lignin

Definitions

  • the present invention relates to a process for preparing a bonding resin, wherein a first resin prepared from lignin, formaldehyde and optionally phenol is mixed with a second resin prepared from lignin, formaldehyde and optionally phenol, wherein the first resin is different from the second resin, to achieve a mixture useful as a bonding resin useful in the manufacture of laminates, mineral wool insulation and wood products such as plywood, laminated veneer lumber (LVL), medium density fiberboards (MDF) and particle boards.
  • a first resin prepared from lignin, formaldehyde and optionally phenol is mixed with a second resin prepared from lignin, formaldehyde and optionally phenol, wherein the first resin is different from the second resin, to achieve a mixture useful as a bonding resin useful in the manufacture of laminates, mineral wool insulation and wood products such as plywood, laminated veneer lumber (LVL), medium density fiberboards (MDF) and particle boards.
  • LDL laminated veneer lumber
  • MDF medium density
  • 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.
  • 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).
  • novolacs when utilizing acidic catalysts
  • resoles when utilizing basic catalysts
  • One problem when preparing resins comprising lignin is to optimize the properties of the final resin for different products.
  • resins need to have different properties depending on end use, numerous different resins, i.e. individual resins having different properties, need to be produced and sometimes stored, to allow the production of a range of final end products.
  • the present invention is thus directed to a method for preparing a resin in the form of a mixture comprising the steps of
  • the first resin can be prepared using methods known in the art. For example, lignin can be dissolved into an aqueous medium comprising alkali. The dissolution of the lignin may be carried out with or without heating. In a subsequent step, formaldehyde and optionally phenol is added to the solution, separately or simultaneously. The reaction mixture is heated to approximately 40-95°C until the reaction is completed and desirable properties, such as viscosity, have been achieved.
  • the amount of lignin used in the preparation of the resin is typically such that lignin has replaced phenol to a replacement level of 40-100% in the first resin used in the context of the present invention. Thus, the lignin reacts during the preparation of the first resin.
  • Lignin may be utilized as a powder at the time that it is incorporated into the resin formulation. Lignin can also be utilized in“liquid form” in an alkali solution in order to avoid lignin dust.
  • the second resin can be prepared using methods known in the art.
  • the second resin can be prepared in the same way as the first resin.
  • the second resin is different from the first resin.
  • the lignin has typically replaced phenol to a replacement level of 5-100%. Thus, the lignin reacts during the preparation of the second resin.
  • the difference between the first resin and the second resin can for example be the lignin content, such as the degree to which lignin has replaced phenol.
  • the difference between the first and the second resin can also be the solid content, viscosity, pH or any other property.
  • the first resin and the second resin may prepared in any order prior to being mixed with each other.
  • the step of mixing the first resin and the second resin can be carried out at room temperature. However, it is preferable to carry out the mixing step at a temperature of from 20°C to 35°C.
  • the mixing can be carried using traditional mixing equipment and the mixing can be carried out batch-wise or
  • the mixing is preferably carried out such that the stirring is performed at less than 10000 rpm, more preferably in the range of from 10 to 5000 rpm, such as from 10 to 1000 rpm, particular 20 to 500 rpm.
  • the mixing is typically carried out for at least one minute, such as from 1 minute to 2 hours, depending on the volume of the mixture being prepared.
  • the viscosity of the mixture of the first resin and the second resin is preferably monitored, either on a continuous basis or by taking samples at defined time intervals.
  • the amount of each of the first resin and the second resin that is added to provide the mixture of the first resin and the second resin depends on the intended use of the mixture and the required properties necessary for that use. Typically, the amount of each of the first resin and second resin is added according to a predetermined recipe such that the mixture of the first resin and the second resin yields the desired properties.
  • the step of mixing the first resin and the second resin is carried out until the first resin and the second resin have been adequately mixed, such that the composition of the mixture is essentially homogenous throughout the mixture obtained.
  • the properties of the mixture of the first resin and the second resin can be adjusted by adding additives to the mixture.
  • additives are for example acids or bases, to adjust the pH of the mixture of the first resin and the second resin to a desired pH.
  • the additives may also be colorants, pigments, fire retardants or other additives typically used in the preparation of resins. These additives can also be added in one of the resin before mixing.
  • the mixture may comprise additives and/or additional resins.
  • the present invention is thus also directed to the use of the mixture of the first resin and the second resin in the manufacture of laminates, mineral wool insulation and wood products such as plywood, laminated veneer lumber (LVL), medium density fiberboards (MDF) and particle boards.
  • the present invention is also directed to such laminates, mineral wool insulation and wood products such as plywood, laminated veneer lumber (LVL), medium density fiberboards (MDF) and particle boards manufactured using the mixture of the first resin and the second resin.
  • the present invention is also directed to a method for selecting an optimized resin mixture for a specific end use, comprising the steps of
  • the second resin is different from the first resin; d) mixing the first resin and the second resin in a defined weight ratio of from 0.5: 10 to 10:0.5 based on weight of the mixture of the first resin and second resin;
  • step d) in an empty vessel, repeating step d) with a different weight ratio
  • step f) repeating step e) at least five times with additional different weight ratios in step d) in each repetition;
  • step h) selecting the optimized mixture of the first resin and the second resin obtained in step f), based on the results of the evaluation carried out in step g), said selection step comprising the determination of which mixture of the first resin and second resin obtained in step f) has properties closest to the desired properties of a resin defined in step a).
  • the evaluation of the properties if the resin mixture or product manufactured using the resin mixture can be carried out using methods known in the art.
  • properties of the resin include viscosity, pH, storage time, solid content etc and of the product manufactured using the resin include pressing time, assembly time, reactivity etc.
  • the properties concerned can be determined by the skilled person.
  • lignin embraces any kind of lignin, e.g. lignin originated from hardwood, softwood or annular plants.
  • lignin is an alkaline lignin generated in e.g. the Kraft process.
  • the lignin may then be separated from the black liquor by using the process disclosed in W02006031175.
  • the pH of the mixture of the first resin and the second resin may be adjusted by addition of acid or base, depending on the final use of the mixture of the first resin and the second resin.
  • alkali it is preferably sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide or a mixture thereof.
  • acid it is preferably sulphuric acid or paratoluenesulphonic acid.
  • the mixture of the first resin and the second resin according to the present invention is useful for example in the manufacture of laminate.
  • the mixture of the first resin and the second resin is then impregnated into paper that should form the laminate and said sheets are pressed together and heated at a temperature of about 130-150 °C.
  • the mixture of the first resin and the second resin according to the present invention is also useful for example in the manufacture of plywood.
  • the mixture of the first resin and the second resin is then applied to the surfaces of the plies or veneers that should form the plywood and said plies or veneers are pressed together and heated at a temperature of about 110-180 °C.
  • Lignin-phenol-formaldehyde (LPF) resin was synthesized for plywood application with a phenol replacement level of 50% with lignin.
  • the first step 918 g powder lignin (solid content 91 %) and 1225 g of water were added to a 5L glass reactor at ambient temperature and were stirred until the lignin was fully and evenly dispersed. Then, 426 g of sodium hydroxide solution (50%) was added to the lignin dispersion. The composition was heated to 73°C and stirred for 60 minutes to make sure that lignin was completely dissolved in the alkaline media. Then, the temperature of the lignin composition was lowered to 45 °C.
  • Lignin-phenol-formaldehyde (LPF) resin was synthesized with a phenol replacement level of 20% with lignin.
  • the 66 g of powder lignin (solid content 91 %) and 115 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, 39 g of sodium hydroxide solution (50%) was added to the lignin dispersion. The composition was heated to 80°C and stirred for 60 minutes to make sure that lignin was completely dissolved in the alkaline media. Then, the temperature of the lignin composition was lowered to 45 °C.
  • the resin blend was prepared by mixing LPF resin from example 1 and LPF resin from example 2 in a ratio of 1 : 1 by weight.
  • the resin blend was analyzed and the results of the analysis are given in Table 1 .
  • Birch veneers were sawn to 300 x 300 mm 2 size and conditioned in 20°C, 65% RFI prior to manufacture.
  • Glue comprising resin from example 3 was formulated according to Table 2.
  • Target glue content was 165 g/m 2 which were spread on one side. Pre- pressing was performed at a pressure of 1 .8 MPa for 15 minutes. The close assembly time was 30 minutes. Hot pressing was performed at 127°C with a pressure of 1.8 MPa. The total pressing time was 6 minutes 25 seconds. Prior to evaluation, all samples were conditioned according to EN636 class 3 test method. Shear strength was evaluated according to EN314 test method. Average data from 20 test specimens is presented in Table 3.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Wood Science & Technology (AREA)
  • Forests & Forestry (AREA)
  • Biochemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dry Formation Of Fiberboard And The Like (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne un procédé de préparation d'une résine de collage, une première résine préparée à partir de lignine, de formaldéhyde et éventuellement de phénol étant mélangée avec une deuxième résine préparée à partir de lignine, de formaldéhyde et éventuellement de phénol, la première résine étant différente de la deuxième résine, pour obtenir un mélange utile en tant que résine de collage utile dans la fabrication de stratifiés, d'isolation en laine minérale et de produits à base de bois tels que le contreplaqué, le lamibois (LVL), les panneaux de fibres de densité moyenne (MDF) et des panneaux de particules.
EP19788281.4A 2018-04-20 2019-04-16 Procédé de préparation d'une résine de collage Withdrawn EP3781641A4 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE1850469A SE543465C2 (en) 2018-04-20 2018-04-20 Process for preparing a bonding resin
PCT/IB2019/053099 WO2019202477A1 (fr) 2018-04-20 2019-04-16 Procédé de préparation d'une résine de collage

Publications (2)

Publication Number Publication Date
EP3781641A1 true EP3781641A1 (fr) 2021-02-24
EP3781641A4 EP3781641A4 (fr) 2022-03-23

Family

ID=68239506

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19788281.4A Withdrawn EP3781641A4 (fr) 2018-04-20 2019-04-16 Procédé de préparation d'une résine de collage

Country Status (3)

Country Link
EP (1) EP3781641A4 (fr)
SE (1) SE543465C2 (fr)
WO (1) WO2019202477A1 (fr)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU1680792A (en) * 1991-04-09 1992-11-17 Alcell Technologies Inc. Improved lignin-based wood adhesives
CA2042476C (fr) * 1991-05-13 1999-08-31 Louis R. Calve Adhesifs phenoliques reticules resistants precuits et a durcissement rapide et methode de production connexe
AU4596193A (en) * 1992-04-09 1993-11-18 Alcell Technologies Inc. Lignin in wood composites
WO1994024192A1 (fr) * 1993-04-09 1994-10-27 Alcell Technologies Inc. Formulations a base de lignine destinees a des materiaux composites de bois
FI123934B (en) * 2012-03-29 2013-12-31 Upm Kymmene Corp Use of low molecular weight lignin to prepare a binder composition
US20130292864A1 (en) * 2012-05-03 2013-11-07 Georgia-Pacific Chemicals Llc Methods and systems for adjusting the composition of a binder system containing two or more resins
FR3007764B1 (fr) * 2013-06-26 2016-11-25 Cie Ind De La Matiere Vegetale - Cimv "resine phenolique obtenue par polycondensation de formaldehyde, de phenol et de lignine"
FI126195B (en) * 2014-01-28 2016-08-15 Upm Kymmene Corp Fiber-based product

Also Published As

Publication number Publication date
EP3781641A4 (fr) 2022-03-23
WO2019202477A1 (fr) 2019-10-24
SE543465C2 (en) 2021-02-23
SE1850469A1 (en) 2019-10-21

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