WO2008129056A1 - Matériaux de bois à base de liants contenant des polyamines - Google Patents

Matériaux de bois à base de liants contenant des polyamines Download PDF

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Publication number
WO2008129056A1
WO2008129056A1 PCT/EP2008/054904 EP2008054904W WO2008129056A1 WO 2008129056 A1 WO2008129056 A1 WO 2008129056A1 EP 2008054904 W EP2008054904 W EP 2008054904W WO 2008129056 A1 WO2008129056 A1 WO 2008129056A1
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WO
WIPO (PCT)
Prior art keywords
formaldehyde
amino groups
compound
polyamine
wood
Prior art date
Application number
PCT/EP2008/054904
Other languages
German (de)
English (en)
Inventor
Daniel KÄSMAYR
Stephan WEINKÖTZ
Original Assignee
Basf Se
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 Basf Se filed Critical Basf Se
Publication of WO2008129056A1 publication Critical patent/WO2008129056A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/02—Polyamines
    • 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
    • C08L97/02—Lignocellulosic material, e.g. wood, straw or bagasse
    • 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
    • C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
    • C09J179/02—Polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
    • C08L2666/16—Addition or condensation polymers of aldehydes or ketones according to C08L59/00 - C08L61/00; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen

Definitions

  • the invention relates to a process for the production of wood-based materials containing a binder based on polyamines or polyamine-containing aminoplast resins, wood-based materials obtainable by this process, and special polyamine-containing binders.
  • Wood materials in the context of the invention are materials which are produced by mixing wood particles, for example fibers, chips, strips and wood layers of different thickness, with a binder and subsequent hot pressing.
  • Typical examples of such materials are wood fiber materials such as medium density fiberboard (MDF), chipboard materials such as chipboard and oriented strand board (OSB), plywood such as veneered plywood, and laminated wood.
  • MDF medium density fiberboard
  • OSB oriented strand board
  • plywood such as veneered plywood
  • the binders used are mainly amino resins, in particular melamine-reinforced urea-formaldehyde condensates (mUF resin), phenolic resins and binders based on isocyanates, in particular of polymeric methylene diisocyanate.
  • mUF resin melamine-reinforced urea-formaldehyde condensates
  • phenolic resins binders based on isocyanates, in particular of polymeric methylene diisocyanate.
  • the properties of wood-based materials which contain polyamine-based binders can advantageously be modified if the binder additionally contains a crosslinker which contains at least two primary alcohol groups (-CH 2 OH).
  • the invention therefore provides a process for the production of wood-based materials, wherein
  • (a-1) an aliphatic polyamine having at least three groups selected from the group of primary and secondary amino groups which has a weight-average molecular weight of 600 to 1,000,000 g / mol and is substantially free from other functional groups except for tertiary amino groups (Polyamine P); and or
  • (a-22) a compound (a-22) selected from the group consisting of urea and melamine, wherein the ratio of the amino groups of the compound (a-22) to the formaldehyde is 0.3: 1 to 3.0: 1;
  • step (B) the glued wood particles obtained according to step (A) pressed at elevated temperature to a wood material.
  • the invention furthermore relates to wood-based materials obtainable, preferably obtained, by the process according to the invention.
  • the binder (L) according to the invention is the binder (L) according to the invention and its use as a binder for wood-based materials.
  • Wood-based materials according to the invention are characterized by better mechanical properties, less swelling due to contact with water, lower emissions of formaldehyde and shorter pressing times.
  • wood particles within the meaning of the invention comprises the comminuted and processed wood parts commonly used for the production of the desired wood materials (such as MDF boards and chipboard), for example wood layers, wood strips, wood chips or wood fibers, the latter optionally also of wood fiber-containing plants such as flax, hemp , Sunflowers, Jerusalem artichoke or canola.
  • desired wood materials such as MDF boards and chipboard
  • wood layers, wood strips, wood chips or wood fibers for example wood layers, wood strips, wood chips or wood fibers, the latter optionally also of wood fiber-containing plants such as flax, hemp , Sunflowers, Jerusalem artichoke or canola.
  • Starting materials for wood particles are usually thinning, industrial waste and used wood as well as wood fiber containing plants.
  • sizing solution (L-1) preferred is a solution containing the components (a-1) and (b).
  • sizing solution (L-2) containing the component (a-1), (b) and (c).
  • sizing solution (L-3) containing the component (a-2) and (b).
  • a sizing solution (L-4) containing the component (a-1), (a-2), and (b).
  • sizing solution (L-5) containing the component (a-1), (a-2), (b) and (C).
  • sizing solution (L-6) containing the component (a-2), (b) and (c).
  • the polyamine (P) component (a-1) is an aqueous solution of an aliphatic polyamine having at least 3 functional groups selected from the group of primary and secondary amino groups and having a weight-average molecular weight of 600 to 1,000. 000 g / mol and, apart from tertiary amino groups is substantially free of other functional groups. Essentially free in the sense of the invention means, in particular, that in the case of polyvinylamine partial hydrolysates are included, which may still contain up to about 10% formamide groups or other functions.
  • components (a-1) it is preferred to use polyamines which have a molecular weight of at least 500 g / mol and at least 10 primary or secondary amino groups.
  • Preferred polyamines are poly (ethyleneimine) and poly (vinylamine).
  • the weight-average molecular weight of the polyvinylamine is preferably 5,000 to 250,000 g / mol, more preferably 5,000 to 100,000 g / mol, that of the polyethyleneimine is preferably 500 to 200,000 g / mol, more preferably 800 to 70,000 g / mol, most preferably 2,000 to 50,000 g / mol and in particular 5,000 to 50,000 g / mol.
  • the component (a-1) - if present - contains one or more, preferably one or two, more preferably a polyamine (P).
  • Component (a-2) is an aminoplast resin which is available from:
  • (a-22) a compound (a-22) selected from the group consisting of urea and melamine, wherein the ratio of the amino groups of the compounds (a-22) to the formaldehyde is 0.3: 1 to 3.0: 1;
  • (a-23) a polyamine P, wherein the molar ratio of the sum of the primary, secondary and tertiary amino groups of the polyamine P to the sum of the primary amino groups of the compound (a-22) is 0.0005: 1 to 2000: 1;
  • the compounds (a-24) are, for example, guanidines, thiourea or alkali hydrogen sulphite or alkali metal sulphite.
  • the compounds (a-25) are, for example, carboxylic acids or carboxylic anhydrides, preferably C 1 -C 10 -mono- or di- or polycarboxylic acids or anhydrides, in particular maleic anhydride, succinic anhydride or phthalic anhydride, organic halogen compounds such as Cr to C 1 0-alkyl halides, isocyanates, such as are generally known for preparing polyurethanes, for example, hexamethylene diisocyanate (HDI), toluene diisocyanate (TDI) and polymethylene polyisocyanates (PMDI) , Aldehydes, in particular aliphatic d- to Ci 0 - mono- or dialdehydes, such as succinaldehyde, glutaraldehyde or acetaldehyde, chlorohydrins, in particular epichlorohydrin, or epoxides derived from these chlorohydrins.
  • the preparation of polyamine-modified urea-formaldehyde resins is described in Journal of Applied Polymer Science, 47 (1991) 2957.
  • step 1 an aqueous solution of
  • Formaldehyde such amounts of the compound (a-22) that the ratio of the amino groups of the compound (a-22) to the formaldehyde is 0.1: 1 to 2.0: 1; - such amounts of the polyamine (P) that the molar ratio of the sum of the primary, secondary and tertiary amino groups of the polyamine P to the sum of the primary amino groups of the compound (a-22) is 0.0005: 1 to 2000: 1; optionally up to 0.2 mol per mol of formaldehyde of another compound (a-24); and optionally in amounts up to 0.2 mol per mol of amino groups of the compound (a-25);
  • step 2 if necessary, raising the pH to 6 to 9 and, if necessary, adding such amounts of urea that the final molar ratio of the components (a-21), (a-22), (a-) 23) and (a-24) is reached, and the reaction mixture further reacted at a temperature of 20 to 100 0 C until the solution has a viscosity of 10 to 2,000 mPas.
  • the information on the viscosity refers to samples which were measured at 20 ° C. and adjusted to a solids content of 40% by weight before the measurement.
  • the component (a-2), if present, contains one or more, preferably one or two, more preferably a modified aminoplast resin.
  • the crosslinker component (b) contains one or more, preferably one or two, particularly preferably one, low molecular weight, oligomeric or polymeric crosslinker (V) which contains two or more primary hydroxyl groups.
  • crosslinkers (V) are examples of crosslinkers (V).
  • V-1 aliphatic di- or polyols of the formula (I)
  • R 1 is a straight-chain, branched or cyclic alkylene group having 1 to 10
  • Preferred examples are ethanediol (glycol), 1, 3-propanediol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, trimethylolmethane, trimethylolethane, trimethylolpropane, (2,2-bis-hydroxymethyl-1 butanol), pentaerythritol (2,2-bis-hydroxymethyl-1-butanol) and 1,1,2,2-tetramethylolethane.
  • V-2 sugar alcohols (alditols), in particular of the formula (II),
  • n is a natural number from 1 to 4, for example glycerol, tetrides, such as threitol and erythritol, pentides, such as ribitol, adonite, arabitol and XyNt, and hexitols, such as dulcitol, mannitol and sorbitol.
  • tetrides such as threitol and erythritol
  • pentides such as ribitol, adonite, arabitol and XyNt
  • hexitols such as dulcitol, mannitol and sorbitol.
  • V-3 acyclic and cyclic bis- and oligomethylol-urea derivatives, preferably of the formula (III), O
  • R 2 , R 3 are identical or different H, (C r C 6 ) alkyl or (CH 2 ) n OH
  • n 2 or 3, preferably 2, and
  • n 1 or 2, preferably 1,
  • Examples are 1, 3-dimethylol-4,5-dihydroxyethyleneurea (4,5-dihydroxy-1,3-bis (hydroxymethyl) imidazolidin-2-one), dimethylolethyleneurea (1,3-bis (hydroxymethyl) imidazolidin-2-one) on), di- and trimethyloltriazinones, such as 5-methyl
  • R H, (C 1 -Ce) alkyl, (CH 2 ) n -OH;
  • n 1 or 2;
  • V-5 bis- or polyhydroxymethylated melamine derivatives of the formula (V),
  • R 5 is the same or different H or - (CH 2 ) n OR ';
  • R ' is H or (C r C 4 ) alkyl
  • n is 1, 2, 3 or 4, preferably 1 or 2, more preferably 1,
  • V-6 polyalkylene glycols preferably those of the formula (VI),
  • E is identical or different and is 0-CH 2 -CH 2 or 0-CH 2 -CH (CH 3 ) - and
  • the compounds may be random, alternating or block copolymers in the case of copolymers.
  • polyethylene glycol in particular with a molecular weight of 80 to 2,000.
  • Resole resins of the types which are also used as binders in the production of wood-based materials are preferred, ie. H. Resoles obtainable by base catalyzed condensation of (optionally modified) phenol and formaldehyde in a molar ratio of 1: 1, 5 to 1: 1, 25. Preferably, such a resol is used as an aqueous alkaline solution having an alkali content of 3-10%.
  • crosslinkers V-1 to V-8 mentioned are known and either commercially available or can be prepared by known methods known to the person skilled in the art.
  • V-1) Aliphatic di- or polyols of the formula (I) (V-1) and their preparation are described, for example, in Houben Weyl, Methods of Organic Chemistry and are commercially available from BASF SE, Ludwigshafen, Germany.
  • V-2 Sugar alcohols and their preparation are described, for example, in Römpp Chemie Lexikon, Vol. 6, 9th ed., C. Thieme Verlag, Stuttgart 1995 and the literature cited therein. Such compounds are sold, for example, as food additives.
  • V-3 Methylol ureas and their preparation are described, for example, in Ullmann's Encyclopedia of Industrial Chemistry. Derivatives of these compounds are marketed, for example, by BASF SE under the name Fixapret® crosslinking agents for textile production and processing.
  • V-4) Tris (hydroxymethyl) aminoalkyl compounds and their preparation are described, for example, in Römpp Chemie Lexikon (supra) and the references cited therein.
  • V-5 Melamine derivatives of the formula (V) and their preparation are described, for example, in Römpp Chemie Lexikon (see above) and the literature cited therein. sol che connections are still available under the name Luwipal® ® from BASF SE.
  • V-6 polyalkylene glycols and their preparation are, for example, in Römpp Chemie Lexikon (see above) and described in the literature cited therein, and are typically sold by BASF under the name SE Pluriol ®.
  • V-7 Polyoxymethylenes and their preparation are described, for example, in Römpp Chemie Lexikon (supra) and references cited therein, and are described i.a. from Ticino (Kelsterbach, Germany).
  • V-8 Resole resins and their preparation are described, for example, under the heading phenolic resins in Ullmann's Encyclopedia of Industrial Chemistry and the literature cited therein, and can be obtained, for example, from Hexion AG (Iserlohn, Germany).
  • the optionally contained aminoplast resin (c) is available from
  • Formaldehyde is 0.3: 1 to 3: 1;
  • Such size resins (c) are generally known and described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 1996, VCH Verlagsgesellschaft, Vol. A2, Chapter “Amino Resins", page 115 et seq.
  • the aminoplast resins (c) are basically made in the same way as the aminoplast resins (a2), except that no polyamine (P) is used.
  • the glue solutions according to the invention may furthermore contain customary auxiliaries, such as water repellents, for example paraffins, or wood preservatives.
  • the glue solutions can be mixed with a hardener, for example a carboxylic acid, such as formic acid or an ammonium salt, immediately before processing in order to shorten the curing times.
  • the solids content of the glue solutions is usually determined by pouring a defined amount by weight (about 2 g) of the appropriate solution onto a tray and drying for 2 hours at 120 0 C in a drying oven.
  • the solids content is determined by differential weighing.
  • the sizing solution (L) generally contains 0 to 80 wt .-% (based on the binder) of polyamine (a-1), preferably 10 to 50 wt .-%, particularly preferably 20 to 40 wt .-%.
  • the content of the polyaminomodified aminoplast component (a-2) is generally 0 to 80 wt .-%, preferably 0 to 50 wt .-%, particularly preferably 0 to 25 wt .-%.
  • the content of crosslinker (V) in the size-reducing solution according to the invention is generally from 1 to 30% by weight, preferably from 2 to 30% by weight, particularly preferably from 3 to 10% by weight.
  • the content of the aminoplast resin (C) is generally 0 to 80 wt .-%, preferably 0 to 50 wt .-%, particularly preferably 0 to 25 wt .-%.
  • the content of additives is generally 0 to 5 wt .-%.
  • the amount of water in wt .-% is preferably 1 to 150%, more preferably 2 to 120%.
  • the amount of the amine component ((a-1) and / or (a-2) and optionally (c)) based on atro wood particles is generally 0.1 to 15 wt .-%.
  • the amount of crosslinker based on the amine component is generally from 5 to 100 wt .-%, preferably 5 to 50 wt .-% and particularly preferably 10 to 25 wt .-%.
  • the weight ratio of components (a-1) :( c) is generally 1-10: 10-1.
  • the weight ratio of components (a-1): (a-2) is generally 1-10: 10-1.
  • the weight ratio of components (a-1): (a-2) is generally 1-10: 10-1 and the weight ratio of component a ((a-1) + (a-2 )): (c) generally 1-10: 10-1.
  • the moisture of the wood particles or the water content of the glue is preferably adjusted in step A such that the moisture of the glued wood particles is not more than 150%, preferably 2 to 120%.
  • polyamine component (a) is initially charged and the crosslinker component (b) is then added, more preferably only immediately before the pressing operation in step (B)
  • a sufficient mixing of the components must take place before the pressing process.
  • the gluing of the wood particles in step A takes place according to the methods and conditions which are appropriate for the respective type of wood particles and which are familiar to the person skilled in the art.
  • the gluing can be done by mixer gluing, blow-line gluing or dry gluing.
  • the loading is sizing at low temperatures, preferably carried out from 20 to 40 0 C.
  • step B The gluing of the glued wood particles in step B is carried out according to the conditions appropriate for the respective wood material, as known to those skilled in the art and described for example under the keyword “Wood” in Ullmann's' Encyclopedia of Industrial Chemistry and the literature cited therein.
  • the temperature during pressing (based on the pressure plate) is generally from 150 0 C to 250 0 C, preferably 200 0 C to 240 0 C, the temperature in the middle of the plate for plates with a thickness of> 5 mm is not more than 150 0th C rises and is about 110 0 C in the middle of the plate with conventional chipboard (16 mm).
  • the pressure is generally 1 to 5 N / mm 2 .
  • the pressing times are generally from 2 to 30 s / mm, preferably from 5 to 15 s / mm.
  • the production of MDF boards by the process according to the invention is preferred.
  • the size solutions for producing the MDF boards are applied to the cellulosic fibers by conventional methods (see “MDF - Medium Density Fiberboard", Hans-Joachim Deppe, Kurt Ernst, 1996, DRW-Verlag Weinbringer GmbH & Co., 70771 Leinfelden-Echterdingen, chapter 4.3, pages 81 ff.) -
  • a drying step to adjust a fiber moisture content of 5 to 15%.
  • the glued cellulosic fibers are pressed by a conventional method to fiberboard.
  • a conventional method to fiberboard for example, by sprinkling the glued cellulosic fibers on a support a fiber mat and squeezed them at temperatures of 80 to 250 0 C and at pressures of 5 to 50 bar to fiberboard (see loc. Cit., Chapter 4.5, pages 93ff).
  • the glued cellulosic fibers are scattered to fiber mats of such a layer thickness that result after hot pressing fiberboard with a density of 500 to 900 kg / m3 and a layer thickness of 3 to 40, preferably 3 to 25 mm.
  • the pressing times required for this purpose are usually 3 to 20 seconds per mm thickness of the resulting fiberboard.
  • suitable as smooth surface press tools e.g. two polished steel belts, one of which serves as a support for the fiber mat, or a combination of a polished steel belt as a support and an over-running polished steel roller or a combination of several polished steel rollers.
  • MDF boards can be produced, as required in particular by the furniture industry and the
  • S2S plates smooth-two sides
  • the obtained wood materials especially MDF boards, chipboard and OSB boards can be processed as usual and are particularly suitable for the production of furniture parts.

Abstract

L'invention concerne un procédé de fabrication de matériaux de bois avec lequel des particules de bois sont collées à l'aide d'une solution aqueuse de colle et sont ensuite comprimées à plus haute température pour obtenir le matériau de bois. La solution de colle contient, en plus d'un composant polyaminé, un agent de réticulation qui présente au moins deux groupes alcool primaires.
PCT/EP2008/054904 2007-04-24 2008-04-23 Matériaux de bois à base de liants contenant des polyamines WO2008129056A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07106880 2007-04-24
EP07106880.3 2007-04-24

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WO2008129056A1 true WO2008129056A1 (fr) 2008-10-30

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009080748A1 (fr) * 2007-12-21 2009-07-02 Basf Se Dérivés de glyoxal en tant que liants et agents de réticulation

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2641584A (en) * 1951-10-26 1953-06-09 Du Pont Adhesive compositions, including an amylaceous material and a triazone
DE1569942A1 (de) * 1962-01-18 1969-08-28 Dow Chemical Co Verfahren zur Herstellung von Schichtgebilden
US3642671A (en) * 1969-04-14 1972-02-15 Dow Chemical Co Polyethylenimine-dextrose and/or precursors of dextrose adhesive composition
GB1353546A (en) * 1970-03-19 1974-05-22 Dow Chemical Co Polymer/polyethylenimine -substituted or unsubstituted- adhesive compositions
JPH09157627A (ja) * 1995-12-13 1997-06-17 Sekisui Chem Co Ltd 水溶性粘着剤組成物
WO2001005891A1 (fr) * 1999-07-01 2001-01-25 Basf Aktiengesellschaft Panneaux de fibres a base de polyamines ou de resines aminoplastes contenant de la polyamine comme liants
US20060292952A1 (en) * 2005-06-23 2006-12-28 Building Materials Investment Corporation Fiber mat and process for making same
WO2007149037A1 (fr) * 2006-06-23 2007-12-27 Akzo Nobel Coatings International B.V. Système adhésif et procédé de fabrication d'un produit à base de bois

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2641584A (en) * 1951-10-26 1953-06-09 Du Pont Adhesive compositions, including an amylaceous material and a triazone
DE1569942A1 (de) * 1962-01-18 1969-08-28 Dow Chemical Co Verfahren zur Herstellung von Schichtgebilden
US3642671A (en) * 1969-04-14 1972-02-15 Dow Chemical Co Polyethylenimine-dextrose and/or precursors of dextrose adhesive composition
GB1353546A (en) * 1970-03-19 1974-05-22 Dow Chemical Co Polymer/polyethylenimine -substituted or unsubstituted- adhesive compositions
JPH09157627A (ja) * 1995-12-13 1997-06-17 Sekisui Chem Co Ltd 水溶性粘着剤組成物
WO2001005891A1 (fr) * 1999-07-01 2001-01-25 Basf Aktiengesellschaft Panneaux de fibres a base de polyamines ou de resines aminoplastes contenant de la polyamine comme liants
US20060292952A1 (en) * 2005-06-23 2006-12-28 Building Materials Investment Corporation Fiber mat and process for making same
WO2007149037A1 (fr) * 2006-06-23 2007-12-27 Akzo Nobel Coatings International B.V. Système adhésif et procédé de fabrication d'un produit à base de bois

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 199734, Derwent World Patents Index; AN 1997-369750, XP002488738 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009080748A1 (fr) * 2007-12-21 2009-07-02 Basf Se Dérivés de glyoxal en tant que liants et agents de réticulation

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