WO2005039874A1 - Time released curing system - Google Patents
Time released curing system Download PDFInfo
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- WO2005039874A1 WO2005039874A1 PCT/US2003/030459 US0330459W WO2005039874A1 WO 2005039874 A1 WO2005039874 A1 WO 2005039874A1 US 0330459 W US0330459 W US 0330459W WO 2005039874 A1 WO2005039874 A1 WO 2005039874A1
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- WO
- WIPO (PCT)
- Prior art keywords
- phosphite
- resin
- curable binder
- weight
- binder
- Prior art date
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Classifications
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- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
- C08K5/526—Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl compounds
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- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/10—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with acyclic compounds having the moiety X=C(—N<)2 in which X is O, S or —N
- C08G12/12—Ureas; Thioureas
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C09D161/22—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C09D161/24—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with urea or thiourea
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249924—Noninterengaged fiber-containing paper-free web or sheet which is not of specified porosity
- Y10T428/249925—Fiber-containing wood product [e.g., hardboard, lumber, or wood board, etc.]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]
- Y10T428/249982—With component specified as adhesive or bonding agent
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]
- Y10T428/249982—With component specified as adhesive or bonding agent
- Y10T428/249985—Composition of adhesive or bonding component specified
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]
- Y10T428/249987—With nonvoid component of specified composition
- Y10T428/249991—Synthetic resin or natural rubbers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31942—Of aldehyde or ketone condensation product
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31942—Of aldehyde or ketone condensation product
- Y10T428/31949—Next to cellulosic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31942—Of aldehyde or ketone condensation product
- Y10T428/31949—Next to cellulosic
- Y10T428/31957—Wood
Definitions
- the present invention relates to a curable urea formaldehyde binder composition useful in coated abrasive and engineering wood products.
- the composition includes a curable urea formaldehyde resin and an aryl phosphite.
- This invention relates to abrasive articles in which a thin layer or, more usually, a single layer of abrasive grit is adhesively bonded to a backing.
- Such products are coated abrasives, more commonly referred to as “sandpaper,” and fibrous abrasive pads, for example.
- glue or thermosetting resins such as phenol formaldehyde resins (“PF resins”) and urea formaldehyde resins (“UF resins”) have been used in coating formulations.
- PF resins phenol formaldehyde resins
- UF resins urea formaldehyde resins
- Phenolic resin compositions are known that can cure at ambient temperatures with rapid cure at modestly higher temperatures.
- Such resins as in U.S. Patent No. 5,296,520 to Gerber, provide controlled work time for hardening phenolic resins at ambient temperature using aryl phosphite latent acid catalysts.
- Gerber found that urea and other amide compounds were very effective retarders of ambient temperature hardening of the resin with the aryl phosphite hardening agents.
- UF resins are different from phenolic resins and each have vastly different chemistry and methods of manufacture.
- UF resins are prepared by a condensation whereby the nitrogen of urea reacts with the carbonyl group of formaldehyde.
- an exemplary phenolic polymer is a phenol formaldehyde resin prepared by aromatic substitution of the multiple activated sites of a phenol, initially by formaldehyde, followed by reaction with other reactive intermediates.
- catalysts such as strong base, zinc acetate, and borates can be used to provide phenolic resoles, while strong acid can be used to provide phenolic novolacs.
- UF resins can be prepared using a strong acid catalyst, such as, for example, sulfuric acid. Structurally, phenolic resins are highly aromatic, and contain aromatic end groups. In contrast, UF resins are amino resins and essentially non-aromatic. Regarding curing properties, phenolic polymers range from thermosetting resoles to thermoplastic novolacs. UF resins are thermosetting resins. Accordingly, PF resin chemistry is not predictive of UF resin chemistry, as shown by Gerber, op. cit.
- UF precondensates can be blended with liquid phenolic resin systems.
- such systems are catalyzed by providing a basic environment (pH above 7), in contrast to the acid catalyst used for unblended urea formaldehyde prepolymers.
- curable urea formaldehyde binder compositions employing a latent acid hardening component are needed that will provide desirable working times and curing times under ambient or near ambient conditions.
- the results presented below provide surprising and unexpected improvements in urea formaldehyde based binder compositions.
- a curable binder composition including: a urea formaldehyde resin; and an aryl phosphite.
- a curable binder composition including a urea formaldehyde resin; and an aryl phosphite in an amount ranging from about 0.05% by weight to about 15% by weight, based on the total weight of the resin.
- a curable binder composition using varying concentrations of aryl phosphites there is provided in accordance with one embodiment of the present invention a curable binder composition using varying concentrations of aryl phosphites.
- the unique advantages of the curing system include: improvement in the color of the urea formaldehyde binder to enhance the final product appearance, such as in sand paper; and faster curing to save energy in the engineering wood products industry.
- the color improvement is largely due to the aryl phosphite component.
- Aryl phosphites, acting as anti-oxidants, are known as stabilizers in a wide range of polymers.
- a time released curable urea formaldehyde binder composition there is provided in another embodiment of the present invention.
- aryl phosphites for example triphenyl phosphite, act as accelerators in the pre-formulated curable binder, but in a time released fashion, wherein the determining parameter is temperature.
- the curing system is stable under about 70 °F (about 21 °C), but the curing reaction accelerates above about 80 °F (about 27 °C).
- Working times range from about 0.5 hours to over 100 hours.
- the aryl phosphites of the present invention can be used in an amount ranging from about 0.05% by weight based on the total weight of the resin to about 15% by weight based on the total weight of the resin.
- Urea formaldehyde resins are particularly useful in the binder compositions.
- this time released curable binder composition is useful for coated abrasive products and engineering wood applications.
- the aryl phosphite hardeners of this invention are esters of phosphorous acid which have: two aromatic organic ester groups and an acid hydrogen, three aromatic ester groups, or two aromatic ester groups and one alkyl group.
- the hardener can be a disubstituted phosphorous acid ester such as diphenyl hydrogen phosphite ("DPP") or a trisubstituted phosphorous acid ester such as triphenyl phosphite ("TPP").
- DPP diphenyl hydrogen phosphite
- TPP triphenyl phosphite
- the aryl phosphites of this invention hydrolyze in a controllable manner over a period of time to stronger acidic products and eventually to phosphorous acid.
- Phosphorous acid is a strong acid having an ionization constant pK a of 1.20.
- Phosphorous acid is sufficiently acidic to provide ambient temperature hardening or near ambient temperature hardening of urea formaldehyde resins.
- aryl phosphite hardening agents of this invention can be represented by the general formula (I)
- Ar is aryl and X is selected from hydrogen, aryl, or alkyl.
- aryl phosphites having two ester groups and a hydrogen atom e.g. diphenyl hydrogen phosphite
- DPP diphenyl phosphite
- Useful aryl phosphite hardeners include: diphenyl hydrogen phosphite (DPP); dicresyl (preferably meta or para) hydrogen phosphite; phenyl p-cresyl hydrogen phosphite; phenyl m-cresyl hydrogen phosphite; dinaphthyl hydrogen phosphite; diphenyl isopropyl phosphite; diphenyl methyl phosphite, di(p-cresyl) hexyl phosphite, triphenyl phosphite (TPP), tri(m-cresyl) phosphite, diphenyl isooctyl phosphite, diphenyl 2-ethylhexyl phosphite, diphenyl isodecyl phosphite, diphenyl cyclohexyl phosphi
- the work time of the resin can vary over a broad range by varying the total water content, the use of retarder or accelerator additives, the specific phosphite hardening agent, and its quantity, and temperature.
- the room or ambient temperature hardening compositions of this invention can have a working time of about 15 minutes up to about 20 hours.
- the Shore D hardness can be measured by use of a Durometer Type D of the Shore Instrument & Manufacturing Company located in New York. Another test for ambient temperature hardening is measured by use of a stick applicator wherein the composition consisting of the urea formaldehyde resin, aryl phosphite and water is "stick hard" as described in the Qualitative Flow Procedure set forth hereafter within 24 hours or less after mixing.
- the ambient temperature hardening compositions are preferably those having either a diaryl hydrogen phosphite, a triaryl phosphite or a diaryl monoalkyl phosphite.
- the triaryl phosphite or diaryl monoalkyl phosphite can be pre-hydrolyzed with from about 1%> to 10% of water based on the weight of the aryl phosphite.
- the phosphites having 3 organic substituents can be pre-solvolyzed with water, alkanol, glycol, and mixtures thereof.
- the aryl phosphites of the present invention can be formulated with accelerators. However, these pre- treatments would dampen the time release aspect of the present invention.
- Aryl phosphites having three organic substituents are preferably used as latent hardeners to provide extended periods of stability at ambient temperature for the hardenable compositions and rapid hardening at moderately elevated temperatures such as those not above 60 °C, e.g., about 35 °C to 50 °C.
- latent hardeners can remain fluid for a period of 5 hours or more at a temperature of about 23 °C, but cure rapidly at the higher temperatures, depending on the level of the aryl phosphite.
- diaryl hydrogen phosphites as well as triaryl phosphites or diaryl monoalkyl phosphites can also have extended periods of ambient temperature stability and then be rapidly hardened at moderately elevated temperatures.
- the viscosity of the basic ingredients i.e., urea formaldehyde resin, aryl phosphite, and water, is capable of remaining flowable at ambient temperature for a period of several hours up to over 100 hours, based on the concentration of aryl phosphite.
- the quantity of the aryl phosphite used in this invention can vary over a wide range.
- a preferred range of aryl phosphite can be present in an amount ranging from about 0.05% by weight to about 15% by weight, based on the total weight of the resin.
- DPP is used, a more preferred range is from about 0.1% by weight to about 2% by weight, based on the total weight of the resin; and a most preferred range is from about 0.30% by weight to about 2% by weight, based on the total weight of the resin.
- TPP a more preferred range is from about 0.25%o by weight to about 5% by weight, based on the total weight of the resin.
- the urea formaldehyde resins ("UF resins") of the present invention are aqueous resins and are hardenable using hardeners or accelerators.
- useful UF resins have a U : F molar ratio ranging from about 1 : 1 to about 1:3.5.
- the UF resins of the present invention can have a pH range of from about 4 to about 9.
- formaldehyde scavengers can be employed, e.g. urea, that can be back-added to a urea- formaldehyde resin.
- Modified UF resins can be used in the binders of the present invention.
- Urea-aldehyde resins employed in the coatable binder precursor compositions useful in the invention may be comprised of urea or any urea derivative and any aldehyde which are capable of being rendered coatable, have the capability of reacting together at an accelerated rate in the presence of a catalyst, and which afford an abrasive article with abrading performance acceptable for the intended use.
- the resins comprise the reaction product of an aldehyde and a urea.
- Urea-formaldehyde resins are preferred in the abrasive industry, as noted above, because of their thermal properties, availability, low cost, and ease of handling.
- the urea-aldehyde resins preferably are 30-95%) solids, more preferably 60-80% solids, with a viscosity ranging from about 125 to about 1500 cps (Brookfield viscometer, number 3 spindle, 30 rpm, 25 °C) before addition of water and catalyst and have molecular weight (number average) of at least about 200, preferably varying from about 200 to 700.
- a preferred urea-aldehyde resin for use in the present invention is that known under the trade designation "AL3029R" from Borden Chemical, Inc., Columbus, OH. This is an unmodified (i.e.
- acids having a pK a of 1.20 or less increases the hardening rate of the resin with the aryl phosphite in comparison to the use of acids having a higher pK a .
- acids which have a pK a of 1.2 or less there can be mentioned: sulfamic, oxalic, dichloroacetic, trichloroacetic, methanesufonic, sulfuric, hydrochloric and phenol sulfonic acids.
- Ammonium chloride can be used as a source of hydrochloric acid and/or a buffer solution component.
- Lowering the pH with acids which are less acidic than phosphorous, such as acetic, formic, benzoic, and salicylic acids leads to lower reactivity with the phosphite than when the acid is equal to or greater in acidity than phosphorous acid.
- Catalysts can also be used in the curable binders of the present invention.
- useful catalysts include but are not limited to Lewis acids, for example, aluminum chloride and the like. Preferred are those Lewis acids selected from the group consisting of aluminum chloride, iron (III) chloride, and copper (II) chloride. Particularly preferred is the Lewis acid aluminum chloride in either its non-hydrated form (A1C1 3 ) or hexahydrate form (AlCl 3 «6H 2 O).
- Useful catalysts also include aqueous organic amine salt or ammonium ion salt.
- ammonium ion salt is preferably a salt of ammonium ion (NH + ) and a halide ion such as chloride ion (CL), fluoride ion (F “ ), bromide ion (Br “ ), and the like.
- a particularly preferred ammonium ion salt is ammonium chloride (NH C1).
- Ammonium sulfate ((NH ) 2 SO 4 ), ammonium peroxydisulfate ((NH 4 ) 2 S 2 O 8 ), ammonium thiosulfate ((NH 4 ) 2 S 2 O 3 ), and ammonium nitrate (NH NO 3 ) are deemed suitable for use in the invention as useful ammonium ion salts when used specifically in combination with A1C1 3 as cocatalyst.
- Mixtures of inorganic and organic salts are typically, and in some cases, preferably utilized.
- the hardening reaction of this invention requires water in order to hydro lyze the aryl phosphite, e.g., eventually to phosphorous acid.
- the total water content in the composition i.e. water available for hydrolyzing the phosphite, can vary over a broad range such as that of about 0.15 to 5 parts of water by weight for each part by weight of the aryl phosphite, preferably from about 0.3 to 3 parts of water by weight for each part of the phosphite.
- the requisite total water content can come from any of the ingredients in the composition, e.g., the urea formaldehyde resin, or additional water can be added to the composition.
- the compositions of this invention can include fillers, modifiers, and aggregates which are conventionally used with urea formaldehyde resins.
- the aggregate material may be a particulate material such as that in granular, powder, or flake form. Suitable aggregate materials include but are not limited to: sand, alumina, zirconia, silica, zircon sand, olivine sand, silicon carbide, silicon nitride, boron nitride, bauxite, quartz, chromite, and corundum and mixtures thereof.
- low density aggregate materials such as vermiculite, perlite, and pumice are preferred.
- preferable high density aggregates include: quartz sand, gravel, crushed rock, and broken brick. Fillers such as mica, kaolin, wollastonite, and barites can be used.
- the compositions of the present invention can be used to make coated abrasive articles, for example, sand paper.
- Coatable binder compositions useful in the present invention can contain fillers, fibers, lubricants, grinding aids, antistatic agents, wetting agents, and other additives such as surfactants, pigments, dyes, coupling agents, plasticizers, dispersants, and suspending agents.
- additives such as surfactants, pigments, dyes, coupling agents, plasticizers, dispersants, and suspending agents.
- useful binder precursor compositions may be formulated without these additives, and the additives mixed into the binder precursor just prior to coating onto a substrate.
- the binder compositions of the present invention can include formaldehyde scavengers such as, for example, urea and ammonium compounds.
- Fillers are frequently used in abrasive articles to reduce cost and improve dimensional stability and other physical characteristics. Fillers can be selected from any filler material that does not adversely affect the rheological characteristics of the binder precursors or the abrading performance of the resulting abrasive article. Preferred fillers include calcium metasihcate, aluminum sulfate, alumina trihydrate, cryolite, magnesia, kaolin, quartz, and glass. Fillers that function as grinding aids are cryolite, potassium fluoroborate, feldspar, and sulfur.
- Coated abrasive articles of the invention may be produced by incorporating cured versions of the coatable binder precursor compositions described above.
- the backing may either be a polymeric film, paper sheet, or laminate.
- lignocellulosic materials can be used.
- lignocellulosic materials include, but are not limited to, wood fiber, wood flake, wood strands, wood chips and wood particles, straw, bagasse, wood bark, recycled wood fiber, recycled paper fiber, and mixtures thereof.
- the composite panels produced are known as fiberboard, waferboard, strandboard, oriented strandboard, flakeboard, particleboard and the like.
- the components were mixed thoroughly in the order above at ambient temperature, then placed in a 15 - 20 °C bath. 4 hours, 55 minutes from initial mixing, the viscosity of the reaction mixture was 122.7 cps. After 5 hours, 20 minutes, the mixture was placed in a 32 °C oven. After 6 hours, 5 minutes, the viscosity of the reaction mixture was 149.4 cps.
- the components were mixed thoroughly in the order above at ambient temperature, then placed in a 15 - 20 °C bath. 4 hours, 50 minutes from initial mixing, the viscosity of the reaction mixture was 128.3 cps. After 5 hours, 10 minutes, the mixture was placed in a 32 °C oven. After 6 hours, the viscosity of the reaction mixture was 159.2 cps.
- the components were mixed thoroughly in the order above at ambient temperature, then placed in a 15 - 20 °C bath. 4 hours, 50 minutes from initial mixing, the viscosity of the reaction mixture was 156.3 cps. After 5 hours, 5 minutes, the mixture was placed in a 32 °C oven. After 6 hours, the viscosity of the reaction mixture was 208.2 cps.
- the components were mixed thoroughly in the order above at ambient temperature, then placed in a 15 - 20 °C bath. 4 hours, 45 minutes from initial mixing, the viscosity of the reaction mixture was 188.2 cps. After 4 hours, 55 minutes, the mixture was placed in a 32 °C oven. After 6 hours, the viscosity of the reaction mixture was 456.5 cps. The viscosity continued to rise at about 3.5 cps/second.
- the components were mixed thoroughly in the order above at ambient temperature, then placed in a 15 - 20 °C bath. 4 hours, 15 minutes from initial mixing, the viscosity of the reaction mixture was 116 cps. After 4 hours, 30 minutes, the mixture was placed in a 32 °C oven. After 5 hours, 10 minutes, the viscosity of the reaction mixture was 125.4 cps.
- the components were mixed thoroughly in the order above at ambient temperature, then placed in a 15 - 20 °C bath. 4 hours, 10 minutes from initial mixing, the viscosity of the reaction mixture was 130.1 cps. Then the mixture was placed in a 32 °C oven. After 4 hours, 50 minutes, the viscosity of the reaction mixture was 164.3 cps.
- the binder compositions of the present invention can be engineered to cure in a time released fashion useful for making, for example, coated abrasive products.
- the curing properties of binders having different levels of aryl phosphite are compared. Unexpected improvements in viscosity were observed at relatively low levels of aryl phosphite in the binder. For example, for DPP levels of 0.2 to 0.3%>, viscosity increased 32%) and 334%, respectively. At higher DPP levels, hardening was even more rapid. Additionally, for TPP levels of 1.8 and 5.0%, viscosity increased 17%) and 52%, respectively.
- a curable urea formaldehyde binder composition including an aryl phosphite hardener that acts as an accelerator in a time released fashion.
- the time released curable urea formaldehyde binder composition is useful, for example, in coated abrasive articles.
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP03754923A EP1682347A4 (en) | 2003-09-26 | 2003-09-26 | Time released curing system |
PCT/US2003/030459 WO2005039874A1 (en) | 2003-09-26 | 2003-09-26 | Time released curing system |
AU2003272722A AU2003272722A1 (en) | 2003-09-26 | 2003-09-26 | Time released curing system |
JP2005509918A JP4592589B2 (en) | 2003-09-26 | 2003-09-26 | Sustained release curing system |
BRPI0318512-5A BR0318512A (en) | 2003-09-26 | 2003-09-26 | curable binder composition, coated abrasive article, and processed wood article |
CA2470193A CA2470193C (en) | 2003-09-26 | 2003-09-26 | Time released curing system |
CN038271168A CN1839037B (en) | 2003-09-26 | 2003-09-26 | Time released curing system |
US10/875,877 US7262237B2 (en) | 2003-09-26 | 2004-06-24 | Time released curing system |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US2003/030459 WO2005039874A1 (en) | 2003-09-26 | 2003-09-26 | Time released curing system |
Publications (1)
Publication Number | Publication Date |
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WO2005039874A1 true WO2005039874A1 (en) | 2005-05-06 |
Family
ID=34421189
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/US2003/030459 WO2005039874A1 (en) | 2003-09-26 | 2003-09-26 | Time released curing system |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1682347A4 (en) |
JP (1) | JP4592589B2 (en) |
CN (1) | CN1839037B (en) |
AU (1) | AU2003272722A1 (en) |
BR (1) | BR0318512A (en) |
CA (1) | CA2470193C (en) |
WO (1) | WO2005039874A1 (en) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4268351A (en) * | 1976-12-08 | 1981-05-19 | Henbest Richard G C | Modified urea formaldehyde resin fiber paper |
US6133403A (en) * | 1996-12-23 | 2000-10-17 | Borden Chemical, Inc. | Reactive diluents for acid curable phenolic compositions |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4528344A (en) * | 1984-05-21 | 1985-07-09 | Ppg Industries, Inc. | Low molecular weight resins from nonaromatic polyols and aminoplasts |
DE4035249A1 (en) * | 1990-11-06 | 1992-05-07 | Gruenzweig & Hartmann | MOLDED PART FROM MINERAL WOOL FOR THE CULTIVATION OF PLANTS |
CN1077676A (en) * | 1992-04-16 | 1993-10-27 | 青州市木器厂 | Wood-based plate |
ES2088292T3 (en) * | 1992-09-15 | 1996-08-01 | Minnesota Mining & Mfg | ABRASIVES APPLIED AS COATINGS MADE USING UREA-ALDEHIDE COMPOSITIONS APPLICABLE AS COATINGS CONTAINING A COCATALIZER, AND METHODS FOR MAKING ABRASIVES APPLIED AS COATINGS. |
ES2107311T5 (en) * | 1994-03-15 | 2003-02-16 | Fraunhofer Ges Forschung | PROCEDURE FOR RECOVERY OF CHIPS AND FIBERS BY DISGREGATION OF WASTE MATERIALS DERIVED FROM WOOD, OLD FURNITURE, PRODUCTION WASTE, WASTE AND OTHER MATERIALS CONTAINING MATERIALS DERIVED FROM WOOD. |
US6224800B1 (en) * | 1998-12-17 | 2001-05-01 | Bayer Corporation | Extended polymethylene poly(phenylisocyanate) resin binders for the production of wood composite products |
-
2003
- 2003-09-26 BR BRPI0318512-5A patent/BR0318512A/en not_active IP Right Cessation
- 2003-09-26 WO PCT/US2003/030459 patent/WO2005039874A1/en active Application Filing
- 2003-09-26 EP EP03754923A patent/EP1682347A4/en not_active Withdrawn
- 2003-09-26 CA CA2470193A patent/CA2470193C/en not_active Expired - Fee Related
- 2003-09-26 CN CN038271168A patent/CN1839037B/en not_active Expired - Fee Related
- 2003-09-26 AU AU2003272722A patent/AU2003272722A1/en not_active Abandoned
- 2003-09-26 JP JP2005509918A patent/JP4592589B2/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4268351A (en) * | 1976-12-08 | 1981-05-19 | Henbest Richard G C | Modified urea formaldehyde resin fiber paper |
US6133403A (en) * | 1996-12-23 | 2000-10-17 | Borden Chemical, Inc. | Reactive diluents for acid curable phenolic compositions |
Non-Patent Citations (1)
Title |
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See also references of EP1682347A4 * |
Also Published As
Publication number | Publication date |
---|---|
BR0318512A (en) | 2006-09-12 |
CA2470193A1 (en) | 2005-03-26 |
CN1839037A (en) | 2006-09-27 |
JP2007521351A (en) | 2007-08-02 |
AU2003272722A1 (en) | 2005-05-11 |
CN1839037B (en) | 2010-08-18 |
JP4592589B2 (en) | 2010-12-01 |
EP1682347A1 (en) | 2006-07-26 |
CA2470193C (en) | 2011-07-19 |
EP1682347A4 (en) | 2010-05-26 |
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