CA1176778A - Polyisocyanate adhesives and wood composites therefrom - Google Patents
Polyisocyanate adhesives and wood composites therefromInfo
- Publication number
- CA1176778A CA1176778A CA000424505A CA424505A CA1176778A CA 1176778 A CA1176778 A CA 1176778A CA 000424505 A CA000424505 A CA 000424505A CA 424505 A CA424505 A CA 424505A CA 1176778 A CA1176778 A CA 1176778A
- Authority
- CA
- Canada
- Prior art keywords
- adhesive composition
- hot
- salt
- fatty acid
- components
- 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.)
- Expired
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
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6484—Polysaccharides and derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/01—Hydrocarbons
-
- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
-
- 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
- C08L2666/28—Non-macromolecular organic substances
- C08L2666/30—Hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Dry Formation Of Fiberboard And The Like (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
A heat-curable adhesive is described comprising a liquid poly-isocyanate, a hydrocarbon oil and a salt of u higher fatty acid The adhesive is fast-curing and has mold release properties. Hot-pressed wood composites have been prepared (e.g. waferboard) with relatively short hot-pressing times and without sticking.
A heat-curable adhesive is described comprising a liquid poly-isocyanate, a hydrocarbon oil and a salt of u higher fatty acid The adhesive is fast-curing and has mold release properties. Hot-pressed wood composites have been prepared (e.g. waferboard) with relatively short hot-pressing times and without sticking.
Description
~7b~78 Thls invention relates to adhesive formulations particularly suitable for forming hot-pressed wood composites, such as particleboard and waferboard. A fast-curing adheæive with non-sticking properties i8 provided fro~ a llquid polyisocyanate, a hydrocarbon oil and a higher fatty acid salt.
Description of the Prior Art Phenolformaldehyde (PF) resins have been used exclusively for some time for outdoor type particleboard and waferboard making. The use of these reslns presents certain disadvantages. The density of boards made from PF resln ls-5-10~ higher than that of aminoplast bonded boards.
The rate of thickness swelling i9 high because of the high alkalinity of the re~in and some discoloration may occur due to diffuslon of unbound phenolic residues. With thick bosrds, press times are long. ~arious polyurethane type adhesives also have been used in these context~.
The use of i60cyanates as an adhesive offers some advantages over PF resins. The denfiity of 4,4'-diphe~ylmethane diisocyanate (MDI) bonded boards may be reduced by 10 to 15% without reducing their strength properties; press times may be reduced since isocyanates do not contain water which would need to be evaporated. ~ith 3-layer particleboard6, a higher proportion of fine particles may be incorporated in the core. The weather resistance of isocyanate-bonded particleboards or waferboards is equal to that of PF-bonded boards and the bond quality is not affected within a broad moisture range, i.e. 0 to ~5%. The disadvantages of iso-cyanate bonding are the high cost of the isocyanate (offset by the above mentioned advantages) and sticking to metal parts which necessitates the use of anti-sticking agents on the metal surfaces.
Polyisocyanate-formaldehyde binder systems are known in forming wood composites with release agent coatings on caul sheets normally being necessary on hot-pressing (~ee United States Patents 3,919,017 and 3,930,110, Shoemaker et al). In United States Patent 3,870,665, 11 ~arch 1975, Diehr et al, the use of polyisocyanates in con~unction with com-pounds which catalyze the formation of isocyanurates from isocyanates as mold release agents, is described. Many types of such catalytic com-pounds are mentioned with one type being certain metal salts of carbox-ylic acids.
~.
..~, " ~ :
.- ~ . ' :
, ~76~
Polyisocyanate adhesive systems used in con~unction wLth selected phosphates as internal mold release agents, are described in Canadian Patent 1,123,817, May 18, 19~2, McLaughlin et al~
It would be desirable to provide alternatives to the release agents mentioned which function internally, are inexpensive, and are readily available.
Description of the Invention According to this invention, a heat-curable adhesive co~position is provided, which does not stick significantly to hot mold surfaces, comprising:
a) a liquid polyisocyanate, b) a hydrocarbon oil, and c) a salt of a higher fatty acid having at least 14 carbon atoms.
The adheslve composition may be in the form of an emulsion in the oil.
The liquid polyisocyanate may be selected from a wide variety ~nown to form adhesive systems. Such polyisocyanates include 4,4'-di phenylmethane diisocyanate; 1,4-butylene diisocyanate; 2,4-toluylene di-isocyanate; 4,4'-biphenylene diisocyanate; hexamethylene dlisocyanate;
and triphenylmethane triisocyanate. Liquid dimers, trimer~, tetramers, etc. (oligomers) thereof may be used.
The hydrocarbon oil is selected from petroleum fractions of light to heavy viscosity, particularly those similar to a ~ineral oil or paraEfin oil. A suitable viscosity range is from about 125 to 350 Saybolt viscosity units at 100F. These oils are non-reactive with the polyisocyanate.
The fatty acid moiety should be selected from those having at least 14 carbon atoms. Suitable fatty acids include myristic, palmitic, stearic, oleic, linoleic, behenic and mixtures thereof. The fatty acid is used ln the form of a salt with a polyvalent cation, for instance, zinc, copper, iron, cobalt, calcium, magnesium, and aluminum. We have found the cations of zinc or calcium very suitable.
The relative proportions of the three components can vary within the approximate range by wt. 100:40-200:5-30. Preferably the proportions are about 100:100:16.
.. ,~
~'7~;778 The hydrocarbon oil and the fatty acld salt have been found to bestow very effective anti-sticking and mold release properties on the polyisocyanate without interfering significantly with the wood adhesi~e properties.
The emulsion formation may be facilitated using small amounts of emulsifiers of the nonionic type, for example, esters or modified esters of fatty acids, such as sorbitan mo~olaurate (Span ~ 20) and polyoxyethylene sorbitan monostearate ~Tween ~ 60), other equivalent emulsifiers and mixtures thereof. The emulsion is very stable and can be sprayed onto the wood with standard spray means. Where any water is present in the emulsion, or where there is a slow reaction between the polyisocyanate and emulsifier used, the emulsion should be used as soon as posslble after preparation.
Compo~ite wood products may be prepared by steps comprising:
i) applying to the wood components, as a mlxture, (a) a liquid polyisocyanate (b) a hydrocarbon oil, and (c) a salt of a higher fatty acid having at least 14 carbon atoms;
ii) sub~ecting the coated components to heat and pressure by hot-press-ing surfaces sufficient to consolidate the componen~s and cure the adhesive; and iii) separating the composite wood product from the hot-pressing surfaces without significant sticking thereto.
The amount of the composition applied to the wood surf2ces normally is within ~he range of about 0.5 to about 5% by wt. of the dry wood compon-ents.
The wood should not be abnormally wet or too dry: a moisture content within the range from about 3 to about 10% by wt, i8 preferred.
Hot-pressing may be carried out at temperatures within the approximate range from 150 to 300C for from about 0.75 to about 15 min., preferably about 1-4 min. at about 200C. Pressures applied suitably are within about 400-1200 psi but these are not critical.
' `
-6~
The following examples are illustrative.
The aspen wafers used in this work were prepared with a labora-tory waferizer~ After sifting, flake thickness varied from 23-30 thou-sandthæ of an inch ~0.58-0.78 mm), the length from 1.0-1.8 inches (25.6-46 mm), and width from 0.25-1.25 inches (6.4-31 mm), the maJority being in the 0.75 in. range (19.2 mm). The wafers were airdried on trays for a few days, then in a forced air oven to a molsture content of 4-6% by wt.
The following will illustrate the preparation and use of a polyisocyanate emulsion in paraffin oil.
Emulsion preparation: An emulsion was prepared having the following composltion, (given in parts by weight per part of polyisocyan-ate) paraffln oil: 1, mixed emulsifier: 0~094, water: 0,085, zlnc stear-ate: 0.162. The polyisocyanate was a mixture of monomer, dimer, trimer and tetramer of 4,4'-diphenylmethane diisocyanate (MDI-E 441 Mobay). The paraffin oil was added to the MDI with vigorous stirring~ then the mixed emulsifler was added, followed by the water and the ~inc stearate. The mixed emulsifler had the following composition: Span 20 [trademark]:
85%; Tween 60 [trademarkl: 15% by weight. These two emulsifying agents were mixed separately, then added to the MDI-paraffin oil mixture.
This procedure could be simpliEied by simply adding the stea-rate powder to the MDI-paraffin oll mixture with strong stirring. An emulsion i8 also obtained which is stable for 2 hours or so, and could be used in this condition.
Spraying and Boardmaking: The emulsion was sprayed shortly after its preparation onto aspen wafers of 4-6% moisture content in a rotary drum equipped with a spraying system. The amount of MDI in the emulsion sprayed was 1.5% oE the weight of oven dried wafers.
The coated wafers were placed in a wooden frame set over a car-bon steel caul plate. This plate was given a light coat of a commercial anti-sticking compound before pressing the first board only. About 1500 gms. of coated wafers were used to give board deDsities varying from 39-41 pounds per cu. ft. The mat was then pressed to stops at 500 psi and 410F (210C) for 3 min. Board thickness was 7/16 inch ~ 2 mm).
Five boards were prepared in this manner without one board sticking to the caul plate~ In a control experiment, the caul plate was similarly coated with an anti-sticking compound, but the wafers were sprayed with the same emulsion containing no zinc stearate. The second board made stuck very badly to the caul plate.
The boards were conditioned at 65% R.H. for a week before determinlng their modulus of rupture (MOR), modulus of elasticity (MOE) and the internal bond strength (IB). The wet MOR was determined after boiling in water for 2 hours. Results are shown in Table I.
TABLE I
Strength Properties of Aspen Poplar Waferboards Adhesive Components MOR MOE IB Densit~
(~ of o.d. wafers) dry wet(psi) psi(10-3) psi lbs/ft Paraffln Zinc MDI Oil Stearate 1.5% 1.5% 0.25~ 4484 2143 8~6 47 39.1 All MOR and IB values exceed CSA Standard 0188, namely, 2000 psi ln the dry state, 1000 psi after 2 hours of boiling in water and 40 psi for IB.
, .~ .
Description of the Prior Art Phenolformaldehyde (PF) resins have been used exclusively for some time for outdoor type particleboard and waferboard making. The use of these reslns presents certain disadvantages. The density of boards made from PF resln ls-5-10~ higher than that of aminoplast bonded boards.
The rate of thickness swelling i9 high because of the high alkalinity of the re~in and some discoloration may occur due to diffuslon of unbound phenolic residues. With thick bosrds, press times are long. ~arious polyurethane type adhesives also have been used in these context~.
The use of i60cyanates as an adhesive offers some advantages over PF resins. The denfiity of 4,4'-diphe~ylmethane diisocyanate (MDI) bonded boards may be reduced by 10 to 15% without reducing their strength properties; press times may be reduced since isocyanates do not contain water which would need to be evaporated. ~ith 3-layer particleboard6, a higher proportion of fine particles may be incorporated in the core. The weather resistance of isocyanate-bonded particleboards or waferboards is equal to that of PF-bonded boards and the bond quality is not affected within a broad moisture range, i.e. 0 to ~5%. The disadvantages of iso-cyanate bonding are the high cost of the isocyanate (offset by the above mentioned advantages) and sticking to metal parts which necessitates the use of anti-sticking agents on the metal surfaces.
Polyisocyanate-formaldehyde binder systems are known in forming wood composites with release agent coatings on caul sheets normally being necessary on hot-pressing (~ee United States Patents 3,919,017 and 3,930,110, Shoemaker et al). In United States Patent 3,870,665, 11 ~arch 1975, Diehr et al, the use of polyisocyanates in con~unction with com-pounds which catalyze the formation of isocyanurates from isocyanates as mold release agents, is described. Many types of such catalytic com-pounds are mentioned with one type being certain metal salts of carbox-ylic acids.
~.
..~, " ~ :
.- ~ . ' :
, ~76~
Polyisocyanate adhesive systems used in con~unction wLth selected phosphates as internal mold release agents, are described in Canadian Patent 1,123,817, May 18, 19~2, McLaughlin et al~
It would be desirable to provide alternatives to the release agents mentioned which function internally, are inexpensive, and are readily available.
Description of the Invention According to this invention, a heat-curable adhesive co~position is provided, which does not stick significantly to hot mold surfaces, comprising:
a) a liquid polyisocyanate, b) a hydrocarbon oil, and c) a salt of a higher fatty acid having at least 14 carbon atoms.
The adheslve composition may be in the form of an emulsion in the oil.
The liquid polyisocyanate may be selected from a wide variety ~nown to form adhesive systems. Such polyisocyanates include 4,4'-di phenylmethane diisocyanate; 1,4-butylene diisocyanate; 2,4-toluylene di-isocyanate; 4,4'-biphenylene diisocyanate; hexamethylene dlisocyanate;
and triphenylmethane triisocyanate. Liquid dimers, trimer~, tetramers, etc. (oligomers) thereof may be used.
The hydrocarbon oil is selected from petroleum fractions of light to heavy viscosity, particularly those similar to a ~ineral oil or paraEfin oil. A suitable viscosity range is from about 125 to 350 Saybolt viscosity units at 100F. These oils are non-reactive with the polyisocyanate.
The fatty acid moiety should be selected from those having at least 14 carbon atoms. Suitable fatty acids include myristic, palmitic, stearic, oleic, linoleic, behenic and mixtures thereof. The fatty acid is used ln the form of a salt with a polyvalent cation, for instance, zinc, copper, iron, cobalt, calcium, magnesium, and aluminum. We have found the cations of zinc or calcium very suitable.
The relative proportions of the three components can vary within the approximate range by wt. 100:40-200:5-30. Preferably the proportions are about 100:100:16.
.. ,~
~'7~;778 The hydrocarbon oil and the fatty acld salt have been found to bestow very effective anti-sticking and mold release properties on the polyisocyanate without interfering significantly with the wood adhesi~e properties.
The emulsion formation may be facilitated using small amounts of emulsifiers of the nonionic type, for example, esters or modified esters of fatty acids, such as sorbitan mo~olaurate (Span ~ 20) and polyoxyethylene sorbitan monostearate ~Tween ~ 60), other equivalent emulsifiers and mixtures thereof. The emulsion is very stable and can be sprayed onto the wood with standard spray means. Where any water is present in the emulsion, or where there is a slow reaction between the polyisocyanate and emulsifier used, the emulsion should be used as soon as posslble after preparation.
Compo~ite wood products may be prepared by steps comprising:
i) applying to the wood components, as a mlxture, (a) a liquid polyisocyanate (b) a hydrocarbon oil, and (c) a salt of a higher fatty acid having at least 14 carbon atoms;
ii) sub~ecting the coated components to heat and pressure by hot-press-ing surfaces sufficient to consolidate the componen~s and cure the adhesive; and iii) separating the composite wood product from the hot-pressing surfaces without significant sticking thereto.
The amount of the composition applied to the wood surf2ces normally is within ~he range of about 0.5 to about 5% by wt. of the dry wood compon-ents.
The wood should not be abnormally wet or too dry: a moisture content within the range from about 3 to about 10% by wt, i8 preferred.
Hot-pressing may be carried out at temperatures within the approximate range from 150 to 300C for from about 0.75 to about 15 min., preferably about 1-4 min. at about 200C. Pressures applied suitably are within about 400-1200 psi but these are not critical.
' `
-6~
The following examples are illustrative.
The aspen wafers used in this work were prepared with a labora-tory waferizer~ After sifting, flake thickness varied from 23-30 thou-sandthæ of an inch ~0.58-0.78 mm), the length from 1.0-1.8 inches (25.6-46 mm), and width from 0.25-1.25 inches (6.4-31 mm), the maJority being in the 0.75 in. range (19.2 mm). The wafers were airdried on trays for a few days, then in a forced air oven to a molsture content of 4-6% by wt.
The following will illustrate the preparation and use of a polyisocyanate emulsion in paraffin oil.
Emulsion preparation: An emulsion was prepared having the following composltion, (given in parts by weight per part of polyisocyan-ate) paraffln oil: 1, mixed emulsifier: 0~094, water: 0,085, zlnc stear-ate: 0.162. The polyisocyanate was a mixture of monomer, dimer, trimer and tetramer of 4,4'-diphenylmethane diisocyanate (MDI-E 441 Mobay). The paraffin oil was added to the MDI with vigorous stirring~ then the mixed emulsifler was added, followed by the water and the ~inc stearate. The mixed emulsifler had the following composition: Span 20 [trademark]:
85%; Tween 60 [trademarkl: 15% by weight. These two emulsifying agents were mixed separately, then added to the MDI-paraffin oil mixture.
This procedure could be simpliEied by simply adding the stea-rate powder to the MDI-paraffin oll mixture with strong stirring. An emulsion i8 also obtained which is stable for 2 hours or so, and could be used in this condition.
Spraying and Boardmaking: The emulsion was sprayed shortly after its preparation onto aspen wafers of 4-6% moisture content in a rotary drum equipped with a spraying system. The amount of MDI in the emulsion sprayed was 1.5% oE the weight of oven dried wafers.
The coated wafers were placed in a wooden frame set over a car-bon steel caul plate. This plate was given a light coat of a commercial anti-sticking compound before pressing the first board only. About 1500 gms. of coated wafers were used to give board deDsities varying from 39-41 pounds per cu. ft. The mat was then pressed to stops at 500 psi and 410F (210C) for 3 min. Board thickness was 7/16 inch ~ 2 mm).
Five boards were prepared in this manner without one board sticking to the caul plate~ In a control experiment, the caul plate was similarly coated with an anti-sticking compound, but the wafers were sprayed with the same emulsion containing no zinc stearate. The second board made stuck very badly to the caul plate.
The boards were conditioned at 65% R.H. for a week before determinlng their modulus of rupture (MOR), modulus of elasticity (MOE) and the internal bond strength (IB). The wet MOR was determined after boiling in water for 2 hours. Results are shown in Table I.
TABLE I
Strength Properties of Aspen Poplar Waferboards Adhesive Components MOR MOE IB Densit~
(~ of o.d. wafers) dry wet(psi) psi(10-3) psi lbs/ft Paraffln Zinc MDI Oil Stearate 1.5% 1.5% 0.25~ 4484 2143 8~6 47 39.1 All MOR and IB values exceed CSA Standard 0188, namely, 2000 psi ln the dry state, 1000 psi after 2 hours of boiling in water and 40 psi for IB.
, .~ .
Claims (15)
1. An adhesive composition, heat-curable in the presence of moisture or hydroxyl compounds, which does not stick significantly to hot mold surfaces, comprising:
(a) a liquid polyisocyanate, (b) a hydrocarbon oil, and (c) a salt of a higher fatty acid having at least 14 carbon atoms.
(a) a liquid polyisocyanate, (b) a hydrocarbon oil, and (c) a salt of a higher fatty acid having at least 14 carbon atoms.
2. The adhesive composition of claim 1 in the form of an emulsion in said oil.
3. The adhesive composition of claim 1 wherein the polyisocyanate is selected from 4,4'-diphenylmethane diisocyanate; 1,4-butylene diiso-cyanate; 2,4-toluylene diisocyanate; 4,4'-biphenylene diisocyanate; hexa-methylene. diisocyanate; triphenylmethane triisocyanate, and oligomers thereof.
4. The adhesive composition of claim 1 wherein the hydrocarbon oil is a petroleum fraction of light to medium viscosity.
5. The adhesive composition of claim 1 wherein the salt of the fatty acid has salt-forming components selected from zinc, calcium, and magnesium.
6. The adhesive composition of claim 1 wherein the salt of the fatty acid has fatty acid moieties selected from myristic, palmitic, stearic, oleic, linoleic and behenic acids.
7. The adhesive composition of claim 1 wherein the relative pro-portions of (a):(b):(c) are within the approximate range 100:40-200:5-30 by wt.
8. The adhesive composition of claim 7 wherein the proportion of (a):(b):(c) is about 100:100:16.
CLAIMS (cont.):
CLAIMS (cont.):
9. The composition of claim 1, 7 or 8 comprising 4,4'-diphenyl-methane diisocyanate and its oligomers, a paraffin oil and zinc stearate.
10. A process for preparing hot-pressed composite wood products, comprising:
(i) applying to the wood components, as a mixture, (a) a liquid polyisocyanate, (b) a hydrocarbon oil, and (c) a salt of a higher fatty acid having at least 14 carbon atoms;
(ii) subjecting the coated components to heat and pressure by hot-pressing surfaces sufficient to consolidate the components and cure the adhesive; and (iii) separating the composite wood product from the hot-pressing surfaces without significant sticking thereto.
(i) applying to the wood components, as a mixture, (a) a liquid polyisocyanate, (b) a hydrocarbon oil, and (c) a salt of a higher fatty acid having at least 14 carbon atoms;
(ii) subjecting the coated components to heat and pressure by hot-pressing surfaces sufficient to consolidate the components and cure the adhesive; and (iii) separating the composite wood product from the hot-pressing surfaces without significant sticking thereto.
11. The process of claim 10 wherein the amount of the polyiso-cyanate applied is from about 0.5 to about 5% by wt. of the dry wood components.
12. The process of claim 11 wherein the relative proportions by wt.
of (a):(b):(c) are within the approximate range 100:40-200:5-30.
of (a):(b):(c) are within the approximate range 100:40-200:5-30.
13. The process of claim 10, 11 or 12 wherein (a), (b) and (c) are applied together as an emulsion.
14. The process of claim 10, 11 or 12 wherein the coated components are hot-pressed in (ii) at temperatures within the approximate range 150 to 300°C for from 0.75 to 15 min.
15. A composite wood product prepared by the process of claim 10, 11 or 12.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000424505A CA1176778A (en) | 1983-03-25 | 1983-03-25 | Polyisocyanate adhesives and wood composites therefrom |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000424505A CA1176778A (en) | 1983-03-25 | 1983-03-25 | Polyisocyanate adhesives and wood composites therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1176778A true CA1176778A (en) | 1984-10-23 |
Family
ID=4124873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000424505A Expired CA1176778A (en) | 1983-03-25 | 1983-03-25 | Polyisocyanate adhesives and wood composites therefrom |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1176778A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0346864A2 (en) * | 1988-06-15 | 1989-12-20 | Glunz Ag | Production method for multi-layered fibre boards |
| US5340852A (en) * | 1993-09-09 | 1994-08-23 | Imperial Chemical Industries Plc | Polyisocyanate composition |
| WO1996003461A1 (en) * | 1994-07-22 | 1996-02-08 | Imperial Chemical Industries Plc | Self-release binder system |
| EP3510091A4 (en) * | 2016-09-09 | 2020-04-08 | Robert N. Clausi | Surface modifying agent formulation |
-
1983
- 1983-03-25 CA CA000424505A patent/CA1176778A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0346864A2 (en) * | 1988-06-15 | 1989-12-20 | Glunz Ag | Production method for multi-layered fibre boards |
| EP0346864A3 (en) * | 1988-06-15 | 1991-12-04 | Glunz Ag | Production method for multi-layered fibre boards |
| US5340852A (en) * | 1993-09-09 | 1994-08-23 | Imperial Chemical Industries Plc | Polyisocyanate composition |
| WO1996003461A1 (en) * | 1994-07-22 | 1996-02-08 | Imperial Chemical Industries Plc | Self-release binder system |
| US5554438A (en) * | 1994-07-22 | 1996-09-10 | Imperial Chemical Industries, Plc | Self-release binder system |
| CN1079412C (en) * | 1994-07-22 | 2002-02-20 | 亨茨曼Ici化学品有限公司 | Self release binder system |
| EP3510091A4 (en) * | 2016-09-09 | 2020-04-08 | Robert N. Clausi | Surface modifying agent formulation |
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