Source: http://www.google.de/patents/US8062394
Timestamp: 2013-05-21 03:49:55
Document Index: 363253131

Matched Legal Cases: ['Application No. 60', 'Application No. 564192', 'Application No. 564192', 'Application No. 2006266124', 'Application No. 2199', 'Application No. 200680029072', 'Application No. 10', 'Application No. 10', 'Application No. 10', 'Application No. 095123355', 'Application No. 2', 'Application No. 06', 'Application No. 095123355', 'Application No. 200680029072']

Patent US8062394 - High-performance resin for abrasive products - Google PatenteSuche Bilder Maps Play YouTube News Gmail Drive Mehr » Erweiterte Patentsuche | Webprotokoll | Anmelden Erweiterte Patentsuche PatenteAn abrasive product includes a plurality of abrasive particles and a resin cured with a polythiol group. A method of preparing the abrasive product includes contacting the plurality of abrasive particles with a curable composition that includes a resin and a polythiol group, and curing the curable composition...http://www.google.de/patents/US8062394?utm_source=gb-gplus-sharePatent US8062394 - High-performance resin for abrasive products Ver�ffentlichungsnummerUS8062394 B2PublikationstypErteilung Anmeldenummer11/476,320 Ver�ffentlichungsdatum22. Nov. 2011Eingetragen28. Juni 2006 Priorit�tsdatum29. Juni 2005Auch ver�ffentlicht unterCN101238178ACN101238178BEP1907476A1EP2295496A1US20070011951US20120130014WO2007005452A1 ErfinderAnthony C. GaetaWilliam C. RiceUrspr�nglich Bevollm�chtigterSaint-Gobain Abrasives, Inc. US-Klassifikation51/298524/594Internationale KlassifikationC08L61/00C09K3/14C04B26/12 UnternehmensklassifikationB24D3/344C08L61/24C08L61/06C08L61/28C08G12/32C08G12/36C08G8/10 Europ�ische KlassifikationB24D 3/34B2C08L 61/28C08G 12/36C08G 12/32C08L 61/24C08G 8/10C08L 61/06ReferenzenPatentzitate (58)Nichtpatentzitate (20)Externe LinksUSPTO USPTO-Zuordnung EspacenetHigh-performance resin for abrasive productsUS 8062394 B2 Zusammenfassung An abrasive product includes a plurality of abrasive particles and a resin cured with a polythiol group. A method of preparing the abrasive product includes contacting the plurality of abrasive particles with a curable composition that includes a resin and a polythiol group, and curing the curable composition to produce the abrasive product. A method of abrading a work surface includes applying an abrasive product to a work surface in an abrading motion to remove a portion of the work surface. A curable composition includes a formaldehyde resin and a polythiol group. A formaldehyde resin is crosslinked by a polythiol group. A method of crosslinking the formaldehyde resin includes reacting the polythiol group with the formaldehyde resin.
37. A method of abrading a work surface, comprising applying an abrasive product to a work surface in an abrading motion to remove a portion of the work surface, the abrasive product including an abrasive material embedded in a crosslinked resin, the crosslinked resin including crosslinks by a polythiol crosslinking group having from 2 to 6 thiol moieties, wherein the resin is selected from the group consisting of aldehyde resins, trimethylolpropane triacrylate and tris (2-hydroxy ethyl)isocyanurate triacrylate. Beschreibung
RELATED APPLICATION This application claims the benefit of U.S. Provisional Application No. 60/695,233, filed on Jun. 29, 2005, the entire teachings of which are incorporated herein by reference.
BACKGROUND OF THE INVENTION Many abrasive products include abrasive particles in a binder, for example, abrasive particles bound to paper in sandpaper, or a bonded abrasive article such as a grinding wheel, formed of abrasive particles and a binder.
SUMMARY OF THE INVENTION It is now found that polythiol additives provide improved properties for abrasive resin binders.
Without wishing to be bound by theory, it is believed that the polythiol can improve the properties of the cured resins, such as crosslinked resins, in several ways. The polythiol is believed to act as a chain transfer agent, which can slow down high polymerization rates of resins when reacted with the polythiol. Curing of some resins without the polythiol is believed to proceed immediately, or nearly so, to high-molecular weight, �vitrified� polymers that can have poor conversion percentages and poor mechanical properties. The polythiol is believed to result in higher percent conversion of some resin monomers, resulting in intermolecular chain extension, avoiding some of the vitrification effects and leading to better properties. Also, it is believed that rotational freedom around the �S� moiety can relieve stress around abrasive grains, which can improve mechanical properties.
FIG. 4 shows a �grain shadowing� effect which is believed to occur during ultraviolet curing of coated abrasive 100.
As used herein, an uncured or uncrosslinked �resin� is a composition for curing or crosslinking comprising one or more components selected from monomers, oligomers, and polymers, and may optionally contain other additives such as colorants, stabilizers, plasticizers, fillers, solvents, antiloading agents, or the like. Generally, a resin includes a mixture of partially polymerized components that harden upon curing, which is typically the result of a crosslinking reaction. The cured or uncrosslinked resin can be cured by initiation with light, electron beam radiation, acid, base, heat, combinations thereof, or the like to form the crosslinked resin. Typically in the invention, the uncured or uncrosslinked resins, such as aldehyde resins, are cured or crosslinked with a polythiol group.
As used herein, a �polythiol crosslinker� or �polythiol group� is an organic moiety and includes at least two thiol (�SH) groups; when crosslinked, the thiols are in the form of a sulfur ether group �S�. Polythiols can be monomers oligomers or polymers having 2, 5, 10, 20, 50, 100 or more thiol groups. Generally, a polythiol group comprises from 2 to 6 thiol groups. In one embodiment, the polythiol group is a non-polymeric organic compound. As used herein, the �non-polymeric � organic compound means that the organic compound includes either no repeating unit, or not more than 10 repeats (preferably not more than 5 repeats) of a repeating unit which a polymer typically includes. In a specific embodiment, the polythiol group is a trithiol or tetrathiol. In a more specific embodiment, the trithiol or tetrathiol is non-polymeric (i.e., a monomer or an oligomer). In a preferred embodiment, the polythiol group can be selected from trimethylolpropane tri(3-mercaptopropionate), trimethylolpropane tri(2-mercaptoacetate), pentaerythritol tetra(3-mercaptopropionate), pentaerythritol tetra(2-mercaptoacetate), polyol-3-mercaptopropionates, polyol-2-mercaptoacetates, polyester-3-mercaptopropionates, polyester-2-mercaptoacetates, ethoxylated trimethylolpropane tri(3-mercaptopropionate), also known under the trade name ETTMP 1300 (Chemical Abstract Service Registry No. 345352-19-4), other polyolesterthiols, other polyolthiols, or the like. In a more preferred embodiment, the polythiol includes pentaerythritol tetra-(3-mercaptopropionate) C(CH2OOCCH2CH2�SH)4). Numerous polythiols are commercially available from BRUNO BOCK Chemische Fabrik GmbH & Co. KG, Marschacht Germany.
In a specific embodiment, the resin to be cured or crosslinked includes an aldehyde resin, preferably a formaldehyde resin, crosslinked with a polythiol group. As used herein, the uncured or uncrosslinked �aldehyde resin� includes polymeric or partially polymerized compositions that are formed by condensation reactions of an aldehyde with nucleophiles, such as amino compounds or phenolic compounds, generating water as a byproduct. As used herein, the �amino compound� means a monomeric compound having at least one amino group (�NH2). Examples of the amino compounds that can be employed in the invention include urea; aminotriazines such as melamine; and mixtures thereof. As used herein, the �phenolic compound� means a monomeric compound having at least one phenolic unit. Examples of the phenolic compounds that can be employed in the invention include phenol; alkyl phenols, such as cresols (e.g., o-cresol, m-cresol and p-cresol), xylenols (e.g., 2,4-xylenol), cardinols, ethyl phenols, propyl phenols, hexyl phenols, nonyl phenols or cahew nut shell liquid; alkenyl phenols, such as isopropenyl phenol; polyhydric phenols, such as resorcin; aryl phenols, such as phenylphenol; a phenolic diol, such as CH2(C6H4OH)2 or C(CH3)2(C6H4OH)2; and mixtures thereof. As used herein, the �aldehyde� means an organic compound having at least one aldehyde group or a functional group that can be converted to an aldehyde group, which is capable of reacting with a phenolic compound as described above. Examples of such aldehydes include formaldehyde; formaldehyde yielding materials such as paraformaldehyde; acetaldehyde; furfural; butyraldehyde; and mixtures thereof.
The substrate in a coated abrasive article may have an optional saturant/size coat, a presize coat and/or a backsize coat. Such coats can be employed to seal the substrate and/or to protect the yam or fibers in the substrate. If the substrate is a cloth material, at least one of these coats may be required. The addition of the presize coat or backsize coat may additionally result in a �smoother� surface on either the front and/or the back side of the substrate.
A fluorescent colorant is a dye or pigment containing a fluorescent organic molecule. Detailed descriptions of fluorescent colorants can be found in Zollinger, H., �Color Chemistry: Synthesis, Properties, and Applications of Organic Dyes and Pigments�, 2nd Ed., VCH, New York, 1991, the entire teachings of which are incorporated herein by reference. As used herein, a fluorescent colorant can be, for example, a xanthene, thioxanthene, fluorene (e.g., fluoresceins, rhodamines, eosines, phloxines, uranines, succineins, sacchareins, rosamines, and rhodols), napthylamine, naphthylimide, naphtholactam, azalactone, methine, oxazine, thiazine, benzopyran, coumarin, aminoketone, anthraquinone, isoviolanthrone, anthrapyridone, pyranine, pyrazolone, benzothiazene, perylene, or thioindigoid. More preferably, a fluorescent colorant is selected from the group consisting of xanthenes, thioxanthenes, benzopyrans, coumarins, aminoketones, anthraquinones, isoviolanthrones, anthrapyridones, pyranines, pyrazolones, benzothiazenes, thioindigoids and fluorenes. Most preferably, the fluorescent colorant is a thioxanthene or thioxanthene.
One skilled in the art knows that for many commercially available colorants, the specific chemical structure of individual derivatives within a class, e.g., thioxanthene derivatives, may not be publicly available. Thus, specific fluorescent colorants are typically referred to by Colour Index (C.I.) name, as defined in �Colour Index International�, 4th Ed. American Association of Textile Chemists and Colorists, Research Triangle Park, NC, 2002. The Colour Index is also available online at www.colour-index.org. The entire teachings of the Colour Index are incorporated herein by reference.
In various embodiments, the colorant can be formed as a printed pattern, for example, to show a logo, an identifying description, a part number, a usage instruction, a safety warning, a wear indicator, a swarf loading indicator, or the like. For example, an abrasive loaded with swarf or an abrasive that is worn can be less effective, thus making a wear indicator or swarf loading indicator useful for indicating to a user that a change in abrasive to improve effectiveness. As used herein, �swarf� refers to abraded workpiece material that can �load� or remain in contact with the abrasive, tending to reduce the effectiveness of the abrasive.
In some embodiments, the cured resins of the invention, such as the crosslinked resins, transmit more visible light compared to a resin that is otherwise identical but is not cured with a polythiol group. As used herein, �visible light� is the range of wavelengths from about 400 nm to about 800 nm. The transparency of the cured resin can be measured using a standard visible spectrometer on an appropriately prepared standard sample. For example, two samples formed as identically dimensioned thin films can be compared and the respective percent transmittance values measured.
In some embodiments, an abrasive product of the invention, including the resin cured with the polythiol group, has increased flexibility, for example by at least about 5% or by at least about 10%, compared to an abrasive product that is otherwise identical except the cured resin, i.e., the product includes an otherwise identical resin but not cured with a polythiol. Flexibility can be measured by suitable methods known in the art, for example, by the use of a Frank Stiffness meter available from Karl Frank in Germany or Gurley Precision Instruments in U.S.A. Typically, flexibility test with such a Frank Stiffness meter measures the amount of force required to bend a sample over a fixed radius to a standard angle, such as between 10 degrees to 60 degrees in 5 degree increments. This can be done in both wrap and weft directions of the sample. The slope of a plot of % force (y-axis) versus angle (x-axis) for each sample yields what is known as the as the �Flex Slope.� The higher the flex slope generally indicates a stiffer product.
EXEMPLIFICATION Example 1 Preparation of Crosslinked Phenol Resins Crosslinked resins for the following examples were prepared by combining a standard commercially available (e.g., Oxychem, Borden, Bakelite -Hexion-, Durez and Dynea) phenol formaldehyde resole resin with the polythiol pentaerythritol tetra-(3-mercaptopropionate) as a percent of total weight ranging among 0%, 5%, 10%, and 20% by weight. The mixture was first dried for 2 hours at 200� F. and then cured at 250� F. for 5 hours to cure, for example crosslink, the resin.
Example 2 The Disclosed Crosslinked Phenol Resins Improve Transparency FIG. 2 is a photograph showing samples of phenolic resin with 0%, 5%, 10%, and 20% by weight of the polythiol pentaerythritol tetra-(3-mercaptopropionate). As can be seen, transparency of samples of phenolic resin with 0%, 5%, 10%, and 20% by weight of the polythiol pentaerythritol tetra-(3-mercaptopropionate) increased with the increase of the percentage of polythiol, suggesting that the percentage of polythiol correlates with increasing transparency. For example, the sample with 0 wt % of the polythiol pentaerythritol tetra-(3-mercaptopropionate) was almost black, while the sample with 20 wt % of the polythiol pentaerythritol tetra-(3-mercaptopropionate) was very bright yellow-orange.
Example 3 The �Grain Shadowing� Effect is Overcome by the Disclosed Abrasives Certain resins can be cured with ultraviolet light irradiation when photoinitiators are employed. FIG. 4 shows a �grain shadowing� effect which is believed to occur during ultraviolet curing of coated abrasive 100. This effect is believed to impair the curing and thus the performance of abrasives bound with such resins. The short-wavelength ultraviolet light 402 can be obscured by abrasive grains 110, which can shadow portions of the resin in make coat 104 and size coat 106 in region 404 shadowed by the grain, preventing it from curing properly and binding grains 104 to substrate 102. Without wishing to be bound by theory, in various embodiments, it is believed that the �grain shadowing� effect can be mitigated by employing a photoinitiator which has an absorption in a wavelength region where the abrasive grains are at least partially transparent, employing ultraviolet transparent fillers such as aluminum trihydrate which can increase scattering and/or diffusion of light to reduce shadowing, employing a photoinitiator that has an absorbance at longer wavelength where the longer wavelength light diffuses more readily around the abrasive particles to reduce shadowing, employing ultraviolet transparent substrate in coated abrasives whereby the resin can be cured by ultraviolet light directed at the other side of the substrate from the coating being cured, or the like.
Example 4 The Photoinitiators Employed in the Disclosed Abrasives Absorb Light Transmitted by the Abrasive Grains, Improving Curing FIG. 5 is a graph of the ultraviolet absorbance of a long wavelength photoinitiator of the invention 500, a short-wavelength initiator 502, and three different abrasive grains 504, 506, and 508. As can be seen, if short-wavelength initiator 502 is employed, there can be significant shadowing by the abrasive grains, particularly grain 504. By employing long wavelength photoinitiator 500, the system can be irradiated with light in a wavelength region above the major absorbance of the grain, e.g., 350 nanometers for grain 504, where photoinitiator 500 has greater absorbance than short-wavelength initiator 502. Also, the abrasive grains can have comparatively lower absorption than in the absorption band of short-wavelength initiator 502, particularly grain 504.
Example 5 Thiol Crosslinked Resins Have Improved Mechanical Properties Samples of cured polymer for mechanical analysis were prepared by mixing a 70/30 ratio of trimethylolpropane triacrylate/tris (2-hydroxy ethyl) isocyanurate triacrylate or TMPTA/ICTA resin (Sartomer 368D, Sartomer, Exton, Pa.) with photoinitiator, aluminum trihydrate filler, pentaerythritol tetra-(3-mercaptopropionate), and then casting films on untreated Mylar followed by ultraviolet curing in a Fusion lab unit (Fusion UV Systems, Inc, Gaithersburg, Md.) containing both a 600 w/inch and 300 w/inch power supply utilizing a �V� and �D� bulbs respectively to cure the samples @30 FPM. The samples were removed from the Mylar film and trimmed and cleaned to provide samples suitable to dynamic mechanical analysis (DMA) testing (� 1/16″ thick X �″ wide X 1″ long).
Example 6 The Disclosed Abrasive Products Have Improved Finishing Properties FIG. 7 is a photograph showing an undesirable random scratch in a workpiece finish. Without wishing to be bound by theory, it is believed that such random scratches occur due to poor adhesion of abrasive particles resulting from poor mechanical properties of the resin binder.
TABLE 1 Abrasive product Ra Rz Rt Polythiol 0.31 2.87 3.95 No polythiol 0.90 4.47 9.22 The surface roughness parameters are measured over an assessment length comprising a straight path taken by a probe (e.g., a mechanical or optical probe) that measures variation in the surface. Ra is the average roughness value over the assessment length on the surface, which describes the average peak height and valley depth or average amplitude of a surface. Rz is an ISO 10 point height parameter, which describes the height difference between the 5 highest peaks and 5 lowest valleys in the assessment length. Rt is a measure of roughness maximum or �topmost roughness� relating the difference between the highest peak and the lowest valley over the entire assessment length.
Example 7 The Disclosed Abrasive Products Have Improved Durability FIGS. 9A and 9B are photographs of coated abrasives after identical use conditions. FIG. 9A is a photograph of a coated abrasive with (TMPTA/ICTA resin) crosslinked with the polythiol pentaerythritol tetra-(3-mercaptopropionate); FIG. 9B a photograph of an abrasive having the same resin without polythiol. As can be seen, the resin without polythiol is comparatively rougher and more degraded, with many apparently loosened or missing abrasive grains compared to the coated abrasive with polythiol.
Example 8 The Disclosed Abrasive Products Have Improved Flexibility and Adhesion The polythiol modifier (PTM) modified coated abrasive structures were evaluated for flexibility, peel strength and adhesion in this example. Test samples were prepared under the same process conditions, maintaining coat weights constant, while varying the amount of PTM in either the make or size layer from 0 to 10%, as detailed below.
TABLE 2 PTM Modified Make Formulation Make Formulation Component Vendor Percentage Filler NYAD Wollast 325 NYCO 34% Wet Witcona 1260 Witco 0.10% Resin, Single Comp 94-908 Durez 57% Nalco 2341 Defoamer Nalco 0.10% PET-3MP (PTM) Bruno Bloc 5.70% Water � 3.10% The coated abrasive structures were then coated with 13 pounds per ream of a phenol formaldehyde size coat. The detailed composition of the size coat is presented in Table 3. The web was again transported through a drier which had a dry bulb temperature setting of 120� C. for a period of two hours.
Flexibility was ascertained using a Frank Stiffness meter available from Karl Frank in Germany. This test measured the amount of force required to bend the sample between 10 degrees to 60 degrees in 5 degree increments. The slope of a plot of % force (y-axis) versus angle (x-axis) for each sample yields what is known as the as the �Flex Slope.� The higher the flex slope generally indicates a stiffer product. Three (3) test sample pieces, each of which was 1″ wide�3″ long, were used.
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