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WO1998037147A2 - Composition adhesive et son utilisation - Google Patents

Composition adhesive et son utilisation Download PDF

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Publication number
WO1998037147A2
WO1998037147A2 PCT/IB1998/000607 IB9800607W WO9837147A2 WO 1998037147 A2 WO1998037147 A2 WO 1998037147A2 IB 9800607 W IB9800607 W IB 9800607W WO 9837147 A2 WO9837147 A2 WO 9837147A2
Authority
WO
WIPO (PCT)
Prior art keywords
carbohydrates
composition according
anyone
phenolic compounds
composition
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.)
Ceased
Application number
PCT/IB1998/000607
Other languages
English (en)
Other versions
WO1998037147A3 (fr
Inventor
Kuo Cheng Shen
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.)
Kc Shen International Ltd
Kronospan GmbH
Original Assignee
Kc Shen International Ltd
Kronospan GmbH
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 Kc Shen International Ltd, Kronospan GmbH filed Critical Kc Shen International Ltd
Priority to AU67435/98A priority Critical patent/AU6743598A/en
Priority to AT98912672T priority patent/ATE264889T1/de
Priority to PCT/IB1998/000607 priority patent/WO1998037147A2/fr
Priority to US09/367,657 priority patent/US6589460B1/en
Priority to EP98912672A priority patent/EP0961813B1/fr
Priority to DE69823338T priority patent/DE69823338T2/de
Priority to PL335165A priority patent/PL190838B1/pl
Publication of WO1998037147A2 publication Critical patent/WO1998037147A2/fr
Publication of WO1998037147A3 publication Critical patent/WO1998037147A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • C08H99/00—Subject matter not provided for in other groups of this subclass, e.g. flours, kernels
    • 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

Definitions

  • Adhesive Composition and its use
  • the present invention relates to the use of water-soluble carbohydrates and phenolic compounds as ermosetting adhesives.
  • exterior grade composite and panel wood products are bonded with synthetic adhesives.
  • Phenol-formaldehyde resin adhesives are used in more than 90 % of exterior grade composite products.
  • the finite supply of fossil fuels, coupled with an increasing global demand for wood products has created a need for an alternative, environmentally sound adhesive system based on renewable resources.
  • the need to produce uniform and high quality composite products from lower cost raw material such as smaller diameter logs, wood processing byproducts such as sawdust and bark, and agricultural wastes, has created a need for improved bonding products and processes.
  • Wood similar to other plant resources, is composed of about 45 to 50 % cellulose, 20 to 35 % hemicellulose, 20 to 25 % lignin, and > 0 to 10 % extractives. Chemically, cellulose is the main structural component of all plant cell walls, and is a linear polysaccharide built up from anhydro glucose units having the general formula ( HJ O O J ),,. Cellulose is the most abundant source of carbohydrates in plants. Upon acid hydrolysis cellulose converts into glucose.
  • Hemicelluloses are a group of heterogenous polysaccharides that, next to cellulose, constitute the most abundant sources of carbohydrates in plants. Hemicellulose, associated with the cell wall, is highly soluble in alkali and is relatively easy to degrade by an acid hydrolysis into simple sugars or sugars acids. Hemicellulose may be repeated by the general formula representing five and six carbon sugars such as pentosan and hexosan. Upon acid hydrolysis hemicellulose converts into various reducing sugars.
  • lignin The third major component of lignocellulose is lignin, which is phenolic in character and acts as the natural binder within the lignocellulose to cement cells together.
  • lignin is phenolic in character and acts as the natural binder within the lignocellulose to cement cells together.
  • the precursors of lignin and its formation in lignocellulosic material are still not completely understood, although recently, considerable progress has been made in this area of research. It is generally accepted that lignin is a polymeric material composed of phenyl propane units that are linked together by carbon to carbon as well as carbon to oxygen (ether) bonds.
  • thermo- setting adhesive suitable for particle board production.
  • Stofko a thermo- setting adhesive suitable for particle board production.
  • K.C. Shen (US-A-5,017,319, EP-B-0, 161 ,766 and EP-A-0,492,016) converted lignocellulosic material directly into both mermosetting resin adhesive and composite products by selectively hydrolyzing and decomposing hemicellulose and/or cellulose fractions, using high pressure steam, into low molecular weight water-soluble resin material including pentose and hexose sugars, sugar polymer, furfural, hydroxymethyl furfural, dehydrated carbohydrates, organic acids and other decomposition products.
  • the water-soluble resin material alone, thus produced, can be used in liquid or powder form as a thermosetting water-proof resin adhesive. Since lignin is believed to be the natural binder within lignocellulose and is phenolic in nature, it has been extensively studied and researched in the past hundred years as a binder for lignocellulosic composite products.
  • the hemicellulose was hydrolysed into water-solubles and removed from the treated lignocellulose before the fibres and lignins received made into hard board. Under high temperature and pressure lignins were melted as a binder to cement fibres into a high density hard board.
  • the water-solubles consisting mainly of reducing sugars, were concentrated into wood molasses commonly used in animal fodder.
  • the well-known Masonite process of making hard board, using natural lignin as binder has been in commercial production since the 1930s in USA and other countries, it is now an industry in decline due to inefficiencies and environmental concerns about the enormous quantities of waste water.
  • Fractionation of the spent sulfite liquor to contain a high proportion of the low molecular weight fraction further improved the adhesive quality.
  • the improved spent sulfite liquor adhesive still required high press temperature and long press time to thermoset or cure into a water-proof bond.
  • tannins there are two types of tannins: condensed and hydrolyzable.
  • Condensed tannins using phenolic components from bark extract or from certain agricultural residues, with the addition of formaldehyde, have been used from time to time as a resin adhesives for bonding plywood and particle board.
  • Tannin extractives from the bark of Acacia (wattle of mimosa bark extract) and the wood of Quebracho normally fortified with a small portion of synthetic phenol-formaldehyde resin have been used in the commercial production of exterior grade plywood and particle board in certain countries.
  • tannin adhesives which have restricted their application for wider commercial use.
  • thermosetting adhesives entirely based on lignocellulose vegetation offer permanent solutions to the wood industry.
  • tannins are relatively expensive and hmited in production quantity, up to 400,000 tons per year worldwide for condensed tannins, a mermosetting adhesive consisting of a minor portion of tannin and a major portion of carbohydrates and lignins would provide a significant economic advantage to the wood industry.
  • the lower cost adhesives will allow for the application of higher resin content to produce new and/or better quality composite products.
  • an adhesive composition comprising a product produced by copolymerization of one or more phenolic compounds and one or more water-soluble carbohydrates; or a mixture comprising one or more phenolic compounds or one or more water-soluble carbohydrates, the one or more phenolic compounds being copolymerizable with the one or more water-soluble carbohydrates.
  • the carbohydrates comprise reducing sugars or other reducing carbohydrates.
  • Example 1 The invention is more in detail but without restriction illustrated by the following Examples: Example 1
  • Chips made from pine were prehydrolysed with sulphuric acid at a concentration 0,01 % based on dry wood at a temperature o 200 ° C for 3 min. For this purpose the chips were sprayed with sulphuric acid solution and treated with pressurized steam at a concentration 0,01 % based on dry wood at a temperature o 200 ° C for 3 min. For this purpose the chips were sprayed with sulphuric acid solution and treated with pressurized steam at
  • This example describes the use of bark extract from Western hemlock in combination with black liquor, a by-product from a wet process hard board mill, for bonding particle board.
  • This example demonstrates the use of water-soluble resin material derived from hydrolyzed pine sawdust and modified with hemlock bark extract and formaldehyde to formulate a copolymer adhesive for bonding particle board.
  • Wet pine sawdust was first impregnated with 0.2 % sulphuric acid in dilute solution and steamed at 10.5 bar (180 ° C) for 30 minutes.
  • the steamed hydrolysed sawdust was eluted with hot water and the solution was evaporated under vacuum to a concentration of about 50 % solids with a pH of 3.5.
  • the yield of water-solubles was about 17 % solids based on the original O.D. weight of pine sawdust.
  • Copolymer 7S6 17.6 9.2 37.2 560 8.2
  • the copolymer liquid resin adhesive had a solids content of about 50 %, a pH of about 4.8, and a viscosity of 378 cps.
  • Commercial poplar wafers were sprayed with the liquid copolymer resin adhesive at a rate of 6 % solids weight based on O.D. weight of poplar wafers.
  • 1 % by weight of molten slack wax was also sprayed onto the wafers.
  • the resinated wafers were hand felted into mats that were hot pressed at
  • This example describes the use of sugar molasses, quebracho tannin, pine bark fine powder and formalin to formulate a copolymer resin adhesive for bonding a 3-layer poplar particle board.
  • the sugar molasses was obtained from a beet sugar refinery with solids content of 68 % and pH of 9.3.
  • Quebracho tannin powder was dissolved into the molasses with sodium hydroxide solution to adjust the pH of the mixture to 12.6 and the solids content of 42 % .
  • - To this mixture was added 10 % dry weight of pine bark powder ( ⁇ 0.125 mm based on O.D. weight of wood particle furnish) and an equal amount of water.
  • 9 % formaldehyde (30 % solution formalin) based on solids weight of tannin powder and beet molasses was added to form a viscous liquid.
  • pine bark powder is particularly beneficial: - direct use of tannin in the pine bark as adhesive and as well as a filler, proportionally enhances bonding efficiency, reduces wood particle furnish in the particle board and acts as a scavenger to reduce free formaldehyde.
  • the sucrose-phenolic copolymer liquid adhesi- ve had a solids content of about 51.3 %, a pH of 6.8 and a viscosity of 142 cps.
  • the corn-syrup phenolic copolymer liquid adhesive had a solid content of 52.5 %, a pH of 5.6 and a viscosity of 395.
  • This example demonstrates the production of exterior grade medium density fibre board (MDF) with addition of liquid mimosa tannin and formaldehyde resin in combi- nation with the water-soluble resin material (carbohydrates) already existing in the pine wood fibre, at a conventional MDF manufacturing facility.
  • MDF medium density fibre board
  • the wet pine fibre had a pH of 3.9 and contained about 16.2 % water-soluble resin material derived from hemicellulose hydrolysis, resulting from the ten minute cooking.
  • the wet fibre was then blended with liquid tannin and formaldehyde solution (20 % solids content) at a rate of 4 % based on O.D. weight of pine fibre and dried to 4 - 6 % M.C. and formed into a mat, which was pressed in a continuous press to produce an 8.5 mm MDF with a density of about 870 kg/m 3 .
  • liquid tannin and formaldehyde solution (20 % solids content) at a rate of 4 % based on O.D. weight of pine fibre and dried to 4 - 6 % M.C. and formed into a mat, which was pressed in a continuous press to produce an 8.5 mm MDF with a density of about 870 kg/m 3 .
  • a 60 gram sample of the liquid adhesive was mixed with 2 kg of AFS GEN 60 sand, resulting in a resin content of 1.5 % by weight of the sand.
  • the resin coated sand was then used to produce 6.3 mm thick tensile specimen (dog bones) by heating hand ram- med sand between a pair of hot plates at 250 ° C for 2, 3 and 4 minutes respectively, to cure and thermoset the resin adhesive. All heated solids turned brownish in colour. Edge retention and surface definition appeared normal. Test results of tensile strenghts, curing time and results from a commercial phenolic resin are summarized in Table 6.

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

Abstract

Afin de produire des planches en copeaux ou en fibres ou bien des articles analogues par liaison de copeaux ou de fibres en matériau de type lignocellulosique particulaire avec des adhésifs à base de tanin, tels que des résines taniques ou des résines contenant du tanin, on pré-hydrolyse le matériau lignocellulosique par addition d'acides, de sels acides ou d'autres composés chimiques libérant de l'acide avant l'addition d'une composition particulaire de matière adhésive.
PCT/IB1998/000607 1997-02-20 1998-02-19 Composition adhesive et son utilisation Ceased WO1998037147A2 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AU67435/98A AU6743598A (en) 1997-02-20 1998-02-19 Adhesive composition and its use
AT98912672T ATE264889T1 (de) 1997-02-20 1998-02-19 Klebstoffzusammensetzung und ihre verwendung
PCT/IB1998/000607 WO1998037147A2 (fr) 1997-02-20 1998-02-19 Composition adhesive et son utilisation
US09/367,657 US6589460B1 (en) 1997-02-20 1998-02-19 Adhesive composition and its use
EP98912672A EP0961813B1 (fr) 1997-02-20 1998-02-19 Composition adhesive et son utilisation
DE69823338T DE69823338T2 (de) 1997-02-20 1998-02-19 Klebstoffzusammensetzung und ihre verwendung
PL335165A PL190838B1 (pl) 1997-02-20 1998-02-19 Kompozycja spoiwa i sposób wytwarzania złącza klejonego

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP97102778.4 1997-02-20
PCT/IB1998/000607 WO1998037147A2 (fr) 1997-02-20 1998-02-19 Composition adhesive et son utilisation

Publications (2)

Publication Number Publication Date
WO1998037147A2 true WO1998037147A2 (fr) 1998-08-27
WO1998037147A3 WO1998037147A3 (fr) 1998-10-22

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ID=11004708

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB1998/000607 Ceased WO1998037147A2 (fr) 1997-02-20 1998-02-19 Composition adhesive et son utilisation

Country Status (1)

Country Link
WO (1) WO1998037147A2 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000023233A1 (fr) * 1998-10-16 2000-04-27 Kostiw Darren J Procede de production d'articles a partir de particules lignocellulosiques et de liant
FR2828128A1 (fr) * 2001-08-01 2003-02-07 Kronospan Tech Co Ltd Panneau de fibres fabrique sous moyenne pression et son procede de fabrication
WO2003013809A1 (fr) * 2001-08-01 2003-02-20 Kronospan Technical Company Ltd. Panneau realise dans un materiau derive du bois et de production ecologique
FR2866633A1 (fr) * 2004-02-23 2005-08-26 Oenologie Immele Composition pour la fabrication de bouchons destines notamment a l'industrie vinicole, bouchon utilisant ladite composition et procede de fabrication dudit bouchon
WO2006114089A1 (fr) * 2005-04-26 2006-11-02 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Procede pour fabriquer des panneaux de fibres a moyenne densite et elements de moulage fibreux a emissions polluantes reduites et faible gonflement
DE102004010196B4 (de) * 2003-03-10 2008-11-13 Andritz Ag Vorrichtung zum Austragen von lignozellulosem Rohmaterial aus einem Kocher und zur Förderung des Rohmaterials zu einem Refiner
EP2193899A1 (fr) * 2008-12-05 2010-06-09 Kronotec Ag Procédé de fabrication de matières dérivées du bois à partir de lignocellulose contenant des produits de broyage et une telle matière dérivée du bois
CN101618565B (zh) * 2009-04-28 2011-02-02 王勇 一种环境友好型木质基复合材料的制造方法
WO2013163242A1 (fr) * 2012-04-27 2013-10-31 Georgia-Pacific Chemicals Llc Produits composites constitués de compositions liantes catalysées à l'acide de lewis comprenant des acides tanniques et des aldéhydes multifonctions
EP2817374B1 (fr) 2011-09-02 2017-06-28 Knauf Insulation Système liant à base de glucides et son procédé de production
CN112300350A (zh) * 2020-11-19 2021-02-02 西南林业大学 一种脲醛树脂胶黏剂改性剂及其应用、改性脲醛树脂胶黏剂及其应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4357194A (en) * 1981-04-14 1982-11-02 John Stofko Steam bonding of solid lignocellulosic material
JPS5855146A (ja) * 1981-09-30 1983-04-01 Sumitomo Deyurezu Kk シエルモ−ルド用フエノ−ル樹脂粘結剤およびそれを用いてなるレジンコ−テツドサンド
SU1639873A1 (ru) * 1989-01-02 1991-04-07 Предприятие П/Я В-2869 Смесь дл изготовлени литейных форм и стержней

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000023233A1 (fr) * 1998-10-16 2000-04-27 Kostiw Darren J Procede de production d'articles a partir de particules lignocellulosiques et de liant
US6666951B1 (en) 1998-10-16 2003-12-23 Darren J. Kostiw Process for the production of articles from treated lignocellulosic particles and a formaldehyde based resin binder
FR2828128A1 (fr) * 2001-08-01 2003-02-07 Kronospan Tech Co Ltd Panneau de fibres fabrique sous moyenne pression et son procede de fabrication
WO2003013809A1 (fr) * 2001-08-01 2003-02-20 Kronospan Technical Company Ltd. Panneau realise dans un materiau derive du bois et de production ecologique
WO2003013808A1 (fr) * 2001-08-01 2003-02-20 Kronospan Technical Company Ltd Panneaux mdf et leur procede de production
EP2476526A1 (fr) 2001-08-01 2012-07-18 Kronoplus Technical AG Plaque MDF et fabrication
DE102004010196B4 (de) * 2003-03-10 2008-11-13 Andritz Ag Vorrichtung zum Austragen von lignozellulosem Rohmaterial aus einem Kocher und zur Förderung des Rohmaterials zu einem Refiner
WO2005090180A1 (fr) * 2004-02-23 2005-09-29 Oenologie Immele S.A. Composition pour la fabrication de bouchons destines notamment a l’industrie vinicole, bouchon utilisant ladite composition et procede de fabrication dudit bouchon
FR2866633A1 (fr) * 2004-02-23 2005-08-26 Oenologie Immele Composition pour la fabrication de bouchons destines notamment a l'industrie vinicole, bouchon utilisant ladite composition et procede de fabrication dudit bouchon
WO2006114089A1 (fr) * 2005-04-26 2006-11-02 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Procede pour fabriquer des panneaux de fibres a moyenne densite et elements de moulage fibreux a emissions polluantes reduites et faible gonflement
EP2193899A1 (fr) * 2008-12-05 2010-06-09 Kronotec Ag Procédé de fabrication de matières dérivées du bois à partir de lignocellulose contenant des produits de broyage et une telle matière dérivée du bois
EP2644340A3 (fr) * 2008-12-05 2014-04-30 Kronotec AG Procédé de fabrication de matières dérivées du bois à partir de lignocellulose contenant des produits de broyage et une telle matière dérivée du bois
CN101618565B (zh) * 2009-04-28 2011-02-02 王勇 一种环境友好型木质基复合材料的制造方法
EP2817374B1 (fr) 2011-09-02 2017-06-28 Knauf Insulation Système liant à base de glucides et son procédé de production
WO2013163242A1 (fr) * 2012-04-27 2013-10-31 Georgia-Pacific Chemicals Llc Produits composites constitués de compositions liantes catalysées à l'acide de lewis comprenant des acides tanniques et des aldéhydes multifonctions
US8674019B2 (en) 2012-04-27 2014-03-18 Georgia-Pacific Chemicals Llc Composite products made with lewis acid catalyzed binder compositions that include tannins and multifunctional aldehydes
CN104334326A (zh) * 2012-04-27 2015-02-04 佐治亚-太平洋化工品有限公司 采用含单宁和多官能醛的路易斯酸催化的粘合剂组合物制造的复合产品
CN112300350A (zh) * 2020-11-19 2021-02-02 西南林业大学 一种脲醛树脂胶黏剂改性剂及其应用、改性脲醛树脂胶黏剂及其应用
CN112300350B (zh) * 2020-11-19 2023-03-24 西南林业大学 一种脲醛树脂胶黏剂改性剂及其应用、改性脲醛树脂胶黏剂及其应用

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