WO2000036020A1 - Extended polymethylene poly(phenylisocyanate) resin binders for the production of wood composite products - Google Patents
Extended polymethylene poly(phenylisocyanate) resin binders for the production of wood composite products Download PDFInfo
- Publication number
- WO2000036020A1 WO2000036020A1 PCT/US1999/029360 US9929360W WO0036020A1 WO 2000036020 A1 WO2000036020 A1 WO 2000036020A1 US 9929360 W US9929360 W US 9929360W WO 0036020 A1 WO0036020 A1 WO 0036020A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- weight
- isomer
- content
- wood
- polyisocyanate
- 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
Links
Classifications
-
- 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
- Composite materials such as oriented stand board, particle board and flake board are generally produced by blending or spraying lignocellulose materials such as wood flakes, wood fibers, wood particles, wood wafers, strips or strands, pieces of wood or other comminuted lignocellulose materials with a binder composition while the comminuted materials are blended by tumbling or agitating them in a blender or like apparatus. After blending sufficiently to form a uniform mixture, the materials are formed into a loose mat, which is compressed between heated platens or plates to set the binder and bond the flakes, strands, strips, pieces, etc. together in densified form.
- Isocyanate prepolymers are among the preferred isocyanate materials which have been used in binder compositions to solve various processing problems, particularly adhesion to press platens and high reactivity.
- U.S. Patent 4,100,328 discloses isocyanate- terminated prepolymers which improve product release from a mold.
- U.S. Patent 4,609,513 also discloses a process in which an isocyanate- terminated prepolymer binder is used to improve product release.
- a binder composition in which a particular type of isocyanate prepolymer is used to improve adhesiveness at room temperature is disclosed in U.S. Patent 5,179,143.
- This prepolymer is prepared by reacting (1 ) about 0.05 to about 0.5 hydroxyl equivalents of a polyol having a functionality of from 2 to 8 and a molecular weight of from about 62 to about 2000 with (2) one equivalent of a polyisocyanate mixture containing (a) from 0 to about 50% by weight of polyphenyl polymethylene polyisocyanate and (b) about 50 to about 100% by weight isomer mixture of diphenylmethane diisocyanate containing 10 to 75% by weight of 2,4'-isomer and 25 to 90% by weight of 4,4'-isomer.
- Pressing of wafer board, oriented strand board, and parallel strand lumber using steam injection and a conventional binder such as a urea- formaldehyde resin or a polymeric diphenylmethane diisocyanate (MDI) is known.
- a conventional binder such as a urea- formaldehyde resin or a polymeric diphenylmethane diisocyanate (MDI)
- MDI polymeric diphenylmethane diisocyanate
- This improved binder has the advantages that it uses less of the relatively expensive polyisocyanate to provide properties comparable to traditional MDI binders.
- the reactive amine containing extenders act as carriers for the liquid binder. These extenders do not contain additional water which can increase press cycle times. The tendency of the resin to adhere to the platens may also be reduced.
- the process comprises a) combining wood particles with (2) a polymethylene poly(phenyl isocyanate) having a functionality of about 2.1 to about 3.5, an NCO group content of from about 30 to 33%, and a monomer content of from about 30 to about 90% by weight, wherein the content of the monomer comprise up to about 5% by weight of the 2,2'-isomer, from about 1 to about 20% by weight of the 2,4'-isomer and from about 25% to about 65% by weight of the 4,4'-isomer, based on the entire weight of the polyisocyanate; b) coating the combination from a) with (1 ) a solid, dry compound selected from the group consisting of urea, melamine and mixtures thereof; and c) molding or compressing the coated combination formed in b).
- a polymethylene poly(phenyl isocyanate) having a functionality of about 2.1 to about 3.5, an NCO group content of from about 30 to 33%, and a monomer content of from about 30
- Suitable polyisocyanates to be used as component (2) of the compositions in the present invention include those polymethylene poly(phenylisocyanate) compositions and blends having a NCO group content of about 25% to 33% by weight, and having a viscosity of less than about 2,000 cps at 25 °C.
- the mixtures of solid amines and polyisocyanate have the consistency of a moist powder or that of brown sugar.
- the powdered binder formulations are applied to wood particles in the manufacture of particle board, wafer board, fiber board, etc., by intermixing a stream of wood particles with a stream of the powdered binder formulation at the desired ratio and using mechanical agitation which is in common usage in the manufacture of composite products such as particle board.
- the wood may have a wide range of moisture content, i.e., from about 0.5 to about 10% by weight, based on the total weight of the wood particles.
- Suitable solid, dry compounds to be used as component (1 ) of the present invention include urea, melamine, and mixtures thereof.
- the dry, solid urea, melamine and mixtures thereof contain, for the purposes of this invention, less than 10% by weight of water, and are preferably in the absence of water.
- similar compounds including, but not limited to guanidine or dicyanodiamide can be used, but they are preferably added as mixtures with urea and/or melamine due to their disadvantageous tendency to release ammonia.
- dry means that there is less than 10% by weight of entrained water in the solid.
- the formulation for a particular product will depend upon wood species, requirements of physical properties of the resultant product, and pressing conditions, For example, a formulation range for Douglas fir commercial furnish requirements for interior particle board pressed at a press platten temperature of 350°F for 4.4 minutes press time, to give a high quality commercial product is as follows:
- This binder formulation may be used in an amount of 1 to 25% by weight, expressed as a percentage of the total wood weight, or about 0.25 to 8.0% of PMDI based on the wood weight.
- the quantity of binder formulation based on the weight of the wood is about 2 to 10%, depending on the configuration of the particulate wood and the requirements of the products.
- relatively greater proportions of binder formulation will be used (e.g., 8 to 10% binder formulation, or 1 to 2% isocyanate based on the wood weight).
- Sebacic Acid This substance was purchased from Aldrich Chemical Company, ground using a mortar and pestle, and sieved through a #45 US-mesh sieve. In all cases (with the exception of example 6) for the purpose of this invention, sebacic acid is added at 0.5 weight percent based on the total weight (wood + binder) of every individual formulation.
- Isocyanate A Two parts were combined with one part Sebacic acid in a 32-oz. jar and mixed well. One and one half parts Isocyanate A/Sebacic acid were added to seven parts Melamine. Burundum cylinders were added to the 32-oz. jar, which was then rolled in a roller table for 1 to 1.5 hours. The container was periodically opened, and material clinging to the container walls was scraped off. The binder mix was then sieved through a #45 US-mesh sieve and placed in a catch pan. The catch pan containing the binder was placed in a dessicator for 3 to 4 hours. Procedure for Preparation of Isocyanate A/Urea Binder
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Dry Formation Of Fiberboard And The Like (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR9916219-9A BR9916219A (pt) | 1998-12-17 | 1999-12-10 | Aglutinantes de resina de polimetileno poli(fenil-isocianato) estendido para produção de produtos compósitos de madeira |
| HK02104728.9A HK1042917B (zh) | 1998-12-17 | 1999-12-10 | 用於生產木材複合產品的填充的多亞甲基多(苯基異氰酸酯)樹脂粘合劑 |
| AU31184/00A AU748481B2 (en) | 1998-12-17 | 1999-12-10 | Extended polymethylene poly(phenylisocyanate) resin binders for the production of wood composite products |
| CA002354602A CA2354602C (en) | 1998-12-17 | 1999-12-10 | Extended polymethylene poly(phenylisocyanate) resin binders for the production of wood composite products |
| AT99965219T ATE262565T1 (de) | 1998-12-17 | 1999-12-10 | Gestreckte polymethylene poly(phenylisocyanate) harzbindemittel zur herstellung von holzverbundprodukten |
| EP99965219A EP1141134B1 (en) | 1998-12-17 | 1999-12-10 | Extended polymethylene poly(phenylisocyanate) resin binders for the production of wood composite products |
| DE69915879T DE69915879T2 (de) | 1998-12-17 | 1999-12-10 | Gestreckte polymethylene poly(phenylisocyanate) harzbindemittel zur herstellung von holzverbundprodukten |
| JP2000588274A JP2002532293A (ja) | 1998-12-17 | 1999-12-10 | 木材複合物製品の製造のための伸長ポリメチレンポリ(フェニルイソシアネート)樹脂結合剤 |
| NZ512386A NZ512386A (en) | 1998-12-17 | 1999-12-10 | Extended polymethylene poly(phenylisocyanate) resin binders for the production of wood composite products |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/213,606 US6224800B1 (en) | 1998-12-17 | 1998-12-17 | Extended polymethylene poly(phenylisocyanate) resin binders for the production of wood composite products |
| US09/213,606 | 1998-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2000036020A1 true WO2000036020A1 (en) | 2000-06-22 |
Family
ID=22795760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1999/029360 Ceased WO2000036020A1 (en) | 1998-12-17 | 1999-12-10 | Extended polymethylene poly(phenylisocyanate) resin binders for the production of wood composite products |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6224800B1 (enExample) |
| EP (1) | EP1141134B1 (enExample) |
| JP (1) | JP2002532293A (enExample) |
| CN (1) | CN1124319C (enExample) |
| AT (1) | ATE262565T1 (enExample) |
| AU (1) | AU748481B2 (enExample) |
| BR (1) | BR9916219A (enExample) |
| CA (1) | CA2354602C (enExample) |
| DE (1) | DE69915879T2 (enExample) |
| ES (1) | ES2217870T3 (enExample) |
| HK (1) | HK1042917B (enExample) |
| NZ (1) | NZ512386A (enExample) |
| PL (1) | PL349316A1 (enExample) |
| WO (1) | WO2000036020A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7199168B2 (en) * | 2002-02-13 | 2007-04-03 | Bayer Materialscience Llc | Process for making cellular composites using polymeric isocyanates as binders for hollow filler particles |
| US20040079670A1 (en) * | 2002-10-16 | 2004-04-29 | Ibrahim Sendijarevic | Protective packaging comprised of shape memory foam |
| US20040170856A1 (en) * | 2002-12-04 | 2004-09-02 | Bill Arndell | Laminated wood products and process for making the same |
| US7071248B2 (en) * | 2003-01-21 | 2006-07-04 | Ashland Licensing And Intellectual Property, Llc | Adhesive additives and adhesive compositions containing an adhesive additive |
| US20050054807A1 (en) * | 2003-09-05 | 2005-03-10 | Weyerhaeuser Company | Low-nitrogen content phenol-formaldehyde resin |
| US7141195B2 (en) * | 2003-09-05 | 2006-11-28 | Weyerhaeuser Co. | Process for making engineered lignocellulosic-based panels |
| JP4592589B2 (ja) * | 2003-09-26 | 2010-12-01 | ヘキソン スペシャルティ ケミカルズ インコーポレーテッド | 徐放性硬化系 |
| US20050242459A1 (en) * | 2004-04-29 | 2005-11-03 | Savino Thomas G | Lignocellulosic composite material and method for preparing the same |
| CA2572965A1 (en) * | 2004-07-30 | 2006-03-30 | Mannington Mills, Inc. | Flooring products and methods of making the same |
| US20060086283A1 (en) * | 2004-10-21 | 2006-04-27 | Premier Wood Treating, L.L.C. | Water repellent cellulose preservative |
| US20060128886A1 (en) * | 2004-12-14 | 2006-06-15 | Winterowd Jack G | Low-nitrogen content phenol-formaldehyde resin |
| US20070122616A1 (en) * | 2005-11-30 | 2007-05-31 | Lawson Eric N | Panel containing bamboo and cedar |
| US20090263617A1 (en) * | 2005-08-31 | 2009-10-22 | Huber Engineered Woods Llc | Panel containing bamboo |
| US7459206B2 (en) * | 2005-08-31 | 2008-12-02 | Huber Engineered Woods Llc | Panel containing highly-cutinized bamboo flakes |
| US7625631B2 (en) * | 2005-08-31 | 2009-12-01 | Huber Engineered Woods Llc | Wood panel containing inner culm flakes |
| US20070116940A1 (en) * | 2005-11-22 | 2007-05-24 | Ou Nian-Hua | Panel containing bamboo |
| US7678840B2 (en) * | 2006-11-28 | 2010-03-16 | Bayer Materialscience Llc | Reduction of MDI emissions in cavity filling NVH polyurethane foams |
| US8865287B2 (en) * | 2008-08-13 | 2014-10-21 | Robert A. Haupt | Rapid curing aldehyde resin-polyisocyanate composition and method for producing hybrid polymer |
| WO2015048441A1 (en) | 2013-09-30 | 2015-04-02 | Basf Se | Lignocellulosic composite articles |
| CN104558515B (zh) * | 2015-01-21 | 2017-02-22 | 安徽建筑大学 | 多孔聚合物的制备方法 |
| CN109081902B (zh) | 2017-06-14 | 2020-11-24 | 万华化学集团股份有限公司 | 一种无醛添加的人造板胶粘剂及用其制造的无醛添加人造板 |
| KR102152087B1 (ko) * | 2019-11-28 | 2020-09-04 | 동화기업 주식회사 | 복합코어 마루바닥재의 제조방법 |
| US12091587B2 (en) * | 2021-07-13 | 2024-09-17 | Akzo Nobel Coatings International B.V. | One-component moisture-curable adhesive composition |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57170973A (en) * | 1981-04-15 | 1982-10-21 | Eidai Co Ltd | Production of modified urea resin adhesive |
| US5128407A (en) * | 1991-07-25 | 1992-07-07 | Miles Inc. | Urea extended polyisocyanates |
| JPH08269425A (ja) * | 1995-03-28 | 1996-10-15 | Dantani Plywood Co Ltd | 木材用接着剤 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3666593A (en) | 1969-10-27 | 1972-05-30 | Us Plywood Champ Papers Inc | Process for making a polyisocyanate-impregnated,paper-overlaid panel |
| DE2109686C3 (de) | 1971-03-02 | 1980-09-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung oder Veredlung lignozellulosehaltiger Werkstoffe |
| DE2325926C2 (de) | 1973-05-22 | 1990-08-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von lignozellulosehaltigen Werkstoffen |
| US4100328A (en) | 1976-06-04 | 1978-07-11 | Basf Wyandotte Corporation | Binder composition and process for preparing pressure molded cellulosic articles |
| US4393019A (en) | 1981-11-30 | 1983-07-12 | The United States Of America As Represented By The Secretary Of Agriculture | Method of pressing reconstituted lignocellulosic materials |
| DE3216363A1 (de) | 1982-05-03 | 1983-11-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zum verleimen von lignocellulosehaltigen rohstoffen mit einem praepolymeren auf basis eines urethanmodifizierten diphenylmethandiisocyanatgemisches |
| US4517147A (en) | 1984-02-03 | 1985-05-14 | Weyerhaeuser Company | Pressing process for composite wood panels |
| US4609513A (en) | 1984-08-15 | 1986-09-02 | Jim Walter Research Corp. | Binder composition for manufacture of fiberboard |
| US4617223A (en) | 1984-11-13 | 1986-10-14 | The Mead Corporation | Reinforced paperboard cartons and method for making same |
| CA1255470A (en) | 1985-05-15 | 1989-06-13 | Karl Walter | Process for making a composite wood panel |
| US4944823A (en) | 1985-09-26 | 1990-07-31 | Carbocol, Inc. | Composition for bonding solid lignocellulosic materials |
| US5001190A (en) | 1986-10-28 | 1991-03-19 | Ashland Oil, Inc. | Process for filling space in a structure with a polyurethane composite in the presence of water |
| WO1988003090A1 (en) | 1986-10-28 | 1988-05-05 | Ashland Oil, Inc. | Polyurethane composites comprising a coarse aggregate and certain polyurethane binders |
| US4850849A (en) | 1988-04-29 | 1989-07-25 | Forintek Canada Corp. | Apparatus for steam pressing compressible mat material |
| US5179143A (en) | 1988-07-26 | 1993-01-12 | Bayer Aktiengesellschaft | Process for the preparation of compression molded materials |
| US5140086A (en) | 1988-11-25 | 1992-08-18 | Weyerhaeuser Company | Isocyanate modified cellulose products and method for their manufacture |
| US5008359A (en) | 1988-11-25 | 1991-04-16 | Weyerhaeuser Company | Isocyanate modified cellulose products and method for their manufacture |
| JP2724360B2 (ja) | 1989-06-16 | 1998-03-09 | 武田薬品工業株式会社 | 床下用吸湿シート |
| US5002713A (en) | 1989-12-22 | 1991-03-26 | Board Of Control Of Michigan Technological University | Method for compression molding articles from lignocellulosic materials |
| US5332458A (en) | 1991-04-29 | 1994-07-26 | Weyerhaeuser Co | Corrugated paperboard strength enhancing process |
| GB9012397D0 (en) | 1990-06-04 | 1990-07-25 | Ici Plc | Mold release compositions |
| US5143768A (en) | 1991-08-30 | 1992-09-01 | Weyerhaeuser Company | Laminated dieboard structure |
| US5204176A (en) | 1992-03-03 | 1993-04-20 | The Dow Chemical Company | Structural siding composition |
| US5641819A (en) | 1992-03-06 | 1997-06-24 | Campbell; Craig C. | Method and novel composition board products |
| US5674568A (en) | 1995-10-03 | 1997-10-07 | Bayer Corporation | Treatment of cellulosic fiber products |
-
1998
- 1998-12-17 US US09/213,606 patent/US6224800B1/en not_active Expired - Lifetime
-
1999
- 1999-12-10 AU AU31184/00A patent/AU748481B2/en not_active Ceased
- 1999-12-10 EP EP99965219A patent/EP1141134B1/en not_active Expired - Lifetime
- 1999-12-10 PL PL99349316A patent/PL349316A1/xx unknown
- 1999-12-10 NZ NZ512386A patent/NZ512386A/xx unknown
- 1999-12-10 WO PCT/US1999/029360 patent/WO2000036020A1/en not_active Ceased
- 1999-12-10 BR BR9916219-9A patent/BR9916219A/pt not_active Application Discontinuation
- 1999-12-10 AT AT99965219T patent/ATE262565T1/de not_active IP Right Cessation
- 1999-12-10 CN CN99814493A patent/CN1124319C/zh not_active Expired - Fee Related
- 1999-12-10 JP JP2000588274A patent/JP2002532293A/ja not_active Withdrawn
- 1999-12-10 CA CA002354602A patent/CA2354602C/en not_active Expired - Fee Related
- 1999-12-10 HK HK02104728.9A patent/HK1042917B/zh not_active IP Right Cessation
- 1999-12-10 DE DE69915879T patent/DE69915879T2/de not_active Expired - Lifetime
- 1999-12-10 ES ES99965219T patent/ES2217870T3/es not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57170973A (en) * | 1981-04-15 | 1982-10-21 | Eidai Co Ltd | Production of modified urea resin adhesive |
| US5128407A (en) * | 1991-07-25 | 1992-07-07 | Miles Inc. | Urea extended polyisocyanates |
| JPH08269425A (ja) * | 1995-03-28 | 1996-10-15 | Dantani Plywood Co Ltd | 木材用接着剤 |
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL ABSTRACTS, vol. 98, no. 22, 30 May 1983, Columbus, Ohio, US; abstract no. 180662, "Isocyanate-modified polyurea adhesives" XP002136179 * |
| PATENT ABSTRACTS OF JAPAN vol. 1997, no. 02 28 February 1997 (1997-02-28) * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002532293A (ja) | 2002-10-02 |
| AU3118400A (en) | 2000-07-03 |
| CA2354602C (en) | 2008-10-28 |
| AU748481B2 (en) | 2002-06-06 |
| CA2354602A1 (en) | 2000-06-22 |
| HK1042917B (zh) | 2004-07-09 |
| US6224800B1 (en) | 2001-05-01 |
| EP1141134A1 (en) | 2001-10-10 |
| HK1042917A1 (en) | 2002-08-30 |
| NZ512386A (en) | 2002-12-20 |
| DE69915879D1 (de) | 2004-04-29 |
| EP1141134B1 (en) | 2004-03-24 |
| ATE262565T1 (de) | 2004-04-15 |
| PL349316A1 (en) | 2002-07-15 |
| CN1124319C (zh) | 2003-10-15 |
| ES2217870T3 (es) | 2004-11-01 |
| CN1330691A (zh) | 2002-01-09 |
| DE69915879T2 (de) | 2005-11-24 |
| BR9916219A (pt) | 2001-09-11 |
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