EP1877224A1 - Article abrasif ayant un groupe chromophore active par une reaction - Google Patents

Article abrasif ayant un groupe chromophore active par une reaction

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Publication number
EP1877224A1
EP1877224A1 EP06749490A EP06749490A EP1877224A1 EP 1877224 A1 EP1877224 A1 EP 1877224A1 EP 06749490 A EP06749490 A EP 06749490A EP 06749490 A EP06749490 A EP 06749490A EP 1877224 A1 EP1877224 A1 EP 1877224A1
Authority
EP
European Patent Office
Prior art keywords
abrasive article
abrasive
color
constituent
curing
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.)
Withdrawn
Application number
EP06749490A
Other languages
German (de)
English (en)
Inventor
Xiaorong You
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Saint Gobain Abrasives Inc
Original Assignee
Saint Gobain Abrasives Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Saint Gobain Abrasives Inc filed Critical Saint Gobain Abrasives Inc
Publication of EP1877224A1 publication Critical patent/EP1877224A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B24—GRINDING; POLISHING
    • B24D—TOOLS FOR GRINDING, BUFFING OR SHARPENING
    • B24D11/00—Constructional features of flexible abrasive materials; Special features in the manufacture of such materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B24—GRINDING; POLISHING
    • B24D—TOOLS FOR GRINDING, BUFFING OR SHARPENING
    • B24D3/00—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents
    • B24D3/02—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents the constituent being used as bonding agent
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B24—GRINDING; POLISHING
    • B24D—TOOLS FOR GRINDING, BUFFING OR SHARPENING
    • B24D3/00—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents
    • B24D3/34—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents characterised by additives enhancing special physical properties, e.g. wear resistance, electric conductivity, self-cleaning properties
    • B24D3/342—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents characterised by additives enhancing special physical properties, e.g. wear resistance, electric conductivity, self-cleaning properties incorporated in the bonding agent
    • B24D3/344—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents characterised by additives enhancing special physical properties, e.g. wear resistance, electric conductivity, self-cleaning properties incorporated in the bonding agent the bonding agent being organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/14—Anti-slip materials; Abrasives

Definitions

  • This disclosure in general, relates to abrasive articles and methods for forming same.
  • Abrasive articles such as coated abrasives and bonded abrasives, are used in various industries to machine workpieces, such as by lapping, grinding, or polishing. Machining utilizing abrasive articles spans a wide industrial scope from optics industries, automotive paint repair industries, to metal fabrication industries. In each of these examples, manufacturing facilities use abrasives to remove bulk material or affect surface characteristics of products.
  • Surface characteristics include shine, texture, and uniformity.
  • manufacturers of metal components use abrasive articles to fine and polish surfaces, and oftentimes desire a uniformly smooth surface.
  • optics manufacturers desire abrasive articles that produce defect free surfaces to prevent light diffraction and scattering.
  • Manufactures also desire abrasive articles that have a high stock removal rate for certain applications. However, there is often a trade-off between removal rate and surface quality. Finer grain abrasive articles typically produce smoother surfaces, yet have lower stock removal rates. Lower stock removal rates lead to slower production and increased cost.
  • abrasives have a tendency to leave random surface defects, such as scratches that are deeper than the average stock removal scratches. Such scratches may be caused by grains that detach from the abrasive article, causing rolling indentations. When present, these scratches scatter light, reducing optical clarity in lenses or producing haze or a foggy finish in decorative metal works. Such scratches also provide nucleation points or attachment points that reduce the release characteristics of a surface. For example, scratches in sanitary equipment allow bacteria to attach to surfaces, and scratches in polished reactors allow formation of bubbles and act as surface features for initiating unwanted reactions.
  • an abrasive article has a layer including an epoxy constituent, a cationic photointiator within the epoxy constituent, and a latent colorant configured to change color in response to activation of the cationic photoinitiator.
  • an abrasive article in another exemplary embodiment, includes a polymer matrix, a reaction activated chromophore within the polymer matrix, and particulate abrasive grains.
  • an abrasive article includes a reaction activated chromophore.
  • a method of manufacturing an abrasive article includes initiating a curing process in an abrasive article workpiece.
  • the abrasive article workpiece includes a polymer precursor and a latent colorant.
  • the latent colorant is configured to change color in response to curing.
  • the method also includes determining a target color of the abrasive article workpiece and terminating the curing process when the abrasive article workpiece exhibits the target color.
  • a method of controlling abrasive product quality includes forming an abrasive product comprising a polymeric matrix and a reaction activated chromophore.
  • the reaction activated chromophore is configured to exhibit a color characteristic based on a state of curing.
  • the method also includes inspecting the abrasive product based on the color characteristic and categorizing the abrasive product based on the color characteristic.
  • an abrasive article includes a layer patterned to form a surface structure.
  • the layer includes a material including a polymeric matrix and a reaction activated chromophore, and includes abrasive grains bonded to the layer.
  • FIG. 1 includes an illustration of an exemplary coated abrasive article.
  • FIG. 2 includes an illustration of an exemplary structured abrasive article.
  • FIG. 3 includes an illustration of an exemplary bonded abrasive article.
  • the disclosure is directed to an abrasive article having a layer that is formed of a polymer matrix.
  • the polymer matrix includes a reaction activated chromophore configured to indicate a state of curing.
  • the reactive chromophore includes a latent colorant and a curing byproduct.
  • the curing byproduct may be a byproduct of activating a photoinitiator.
  • the abrasive article may also include particulate abrasive grains.
  • the disclosure is directed to a method of manufacturing an abrasive article.
  • the method includes initiating a curing process on a workpiece, determining a target color exhibited by the workpiece and terminating the curing process based on the target color.
  • the curing process may include photo curing or thermal curing.
  • the disclosure is directed to a method of controlling abrasive product quality.
  • the method includes forming an abrasive product having a polymer matrix and a reaction activated chromophore, inspecting the abrasive product for a color characteristic, and categorizing the abrasive product based on the color characteristic.
  • the color characteristic may, for example, be a target color or color uniformity.
  • the abrasive article is formed by curing a binder formulation.
  • the binder formulation typically includes polymer precursors or polymerizable constituents.
  • the binder formulation may include cationically polymerizable constituents or may include radically polymerizable constituents.
  • the binder formulation includes a catalysts or an initiator, such as a photoinitiator or a thermal intiator, to initiate and facilitate curing.
  • the binder formulation includes a latent colorant. The latent colorant may react with byproduct of the curing, such as species derived from activated initiators, to change color.
  • the abrasive article also includes abrasive particles.
  • the binder formulation is used as a compliant layer, a make coat or a size coat in a coated abrasive article.
  • Abrasive grains may be deposited on the make coat and be overcoated with a size coat.
  • the abrasive grains are mixed with the binder formulation, a mold is filled with the mixture, and the mixture is cured to form a bonded abrasive article.
  • the binder formulation includes a cationically polymerizable constituent.
  • the cationically polymerizable constituent may have epoxy functional groups or oxerane functional groups.
  • the constituents including epoxy functional groups are cationically curable, by which is meant that polymerization or crosslinking of the epoxy group may be initiated by cations.
  • the epoxy constituents can be monomers, oligomers or polymers and are sometimes referred to as "resins.” Such materials may have an aliphatic, aromatic, cycloaliphatic, arylaliphatic, or heterocyclic structure.
  • the epoxy constituents may include epoxy groups as side groups, or the epoxy groups may form part of an alicyclic or heterocyclic ring system. Epoxy groups may also be bound to, for example, siloxane containing backbones.
  • the epoxy constituent may, for example, include at least one liquid component, such that the combination of materials is a liquid.
  • the epoxy constituent can be a single liquid epoxy material, a combination of liquid epoxy materials, or a combination of liquid epoxy material(s) and solid epoxy material(s) soluble in the liquid.
  • An example of a suitable epoxy constituent includes polyglycidyl or poly(methylglycidyl) ester of polycarboxylic acid, poly(oxiranyl) ether of polyether, epoxidised unsaturated fatty acid, or any combination thereof.
  • the polycarboxylic acid can be aliphatic, such as, for example, glutaric acid, adipic acid and the like; cycloaliphatic, such as, for example, tetrahydrophthalic acid; or aromatic, such as, for example, phthalic acid, isophthalic acid, trimellitic acid, or pyromellitic acid; or any combination thereof.
  • the polyether can be poly(tetramethylene oxide).
  • a carboxyterminated adduct for example, of trimellitic acid or polyol, such as, for example, glycerol or 2,2-bis(4- hydroxycyclohexyl)propane may be used.
  • a suitable epoxidised unsaturated fatty acid may be obtained from, for example, linseed oil or perilla oil.
  • a suitable epoxy constituent may include polyglycidyl or poly(-methylglycidyl) ether obtainable by the reaction of a compound having at least one free alcoholic hydroxy group or phenolic hydroxy group and a suitably substituted epichlorohydrin.
  • the alcohol can be acyclic alcohol, such as, for example, ethylene glycol, diethylene glycol, or higher poly(oxyethylene) glycol; cycloaliphatic, such as, for example, 1,3- or 1,4- dihydroxycyclohexane, bis(4-hydroxycyclohexyl)methane, 2,2-bis(4- hydroxycyclohexyl)propane, or l,l-bis(hydroxymethyl)cyclohex-3-ene; or contain aromatic nuclei, such as N,N-bis(2-hydroxyethyl)aniline or p,p'-bis(2- hydroxyethylamino)diphenylmethane.
  • cyclic alcohol such as, for example, ethylene glycol, diethylene glycol, or higher poly(oxyethylene) glycol
  • cycloaliphatic such as, for example, 1,3- or 1,4- dihydroxycyclohexane, bis(4-hydroxycyclohexyl)methane, 2,2-bis(4-
  • the epoxy constituent may be derived from mono nuclear phenol, such as, for example, from resorcinol or hydroquinone, or may be based on polynuclear phenol, such as, for example, bis(4-hydroxyphenyl)methane (bisphenol F), 2,2-bis(4- hydroxyphenyl)propane (bisphenol A), or on condensation products, obtained under acidic conditions, of phenol or cresol with formaldehyde, such as phenol novolac or cresol novolac.
  • mono nuclear phenol such as, for example, from resorcinol or hydroquinone
  • polynuclear phenol such as, for example, bis(4-hydroxyphenyl)methane (bisphenol F), 2,2-bis(4- hydroxyphenyl)propane (bisphenol A), or on condensation products, obtained under acidic conditions, of phenol or cresol with formaldehyde, such as phenol novolac or cresol novolac.
  • a suitable epoxy constituent alternatively may include poly(N-glycidyl) compound, which is, for example, obtainable by dehydrochlorination of the reaction product of epichlorohydrin with an amine that comprise at least two amine hydrogen atoms, such as, for example, n-butylamine, aniline, toluidine, m-xylylene diamine, bis(4-aminophenyl)methane or bis(4-methylaminophenyl)-methane.
  • poly(N-glycidyl) compound which is, for example, obtainable by dehydrochlorination of the reaction product of epichlorohydrin with an amine that comprise at least two amine hydrogen atoms, such as, for example, n-butylamine, aniline, toluidine, m-xylylene diamine, bis(4-aminophenyl)methane or bis(4-methylaminophenyl)-methane.
  • An exemplary poly(N-glycidyl) compound also includes an N,N'-diglycidyl derivative of cycloalkyleneurea, such as ethyleneurea or 1,3- propyleneurea, or a N,N'-diglycidyl derivative of hydantoin, such as of 5,5- dimethylhydantoin.
  • N,N'-diglycidyl derivative of cycloalkyleneurea such as ethyleneurea or 1,3- propyleneurea
  • hydantoin such as of 5,5- dimethylhydantoin.
  • a further example of a suitable epoxy constituent includes poly(S-glycidyl) compound, which is a di-S-glycidyl derivative, which is derived from dithiol, such as, for example, ethane- 1,2-dithiol or bis(4-mercaptomethylphenyl) ether.
  • An additional example of an epoxy constituent is bis(2,3-epoxycyclopentyl)ether, 2,3- epoxy cyclopentyl glycidyl ether, l,2-bis(2,3-epoxycyclopentyloxy)ethane, bis(4- hydroxycyclohexyl)methane diglycidyl ether, 2,2-bis(4-hydroxycyclohexyl)propane diglycidyl ether, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane, 3,4-epoxy-6- methylcyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, di(3,4- epoxycyclohexylmethyl)hexanedioate, di(3 ,4-epoxy-6- methylcyclohexylmethyl)hexanedioate, ethylenebis(3,4-epoxycyclohexanecarboxylate
  • An epoxy resin in which the 1,2-epoxy groups are bonded to different heteroatoms or functional groups may also be useful.
  • a compound includes, for example, the N,N,O- triglycidyl derivative of 4-aminophenol, the glycidyl ether glycidyl ester of salicylic acid, N- glycidyl-N'-(2-glycidyloxypropyl)-5,5-dimethylhydantoin, 2-glycidyloxy-l,3-bis(5,5- dimethyl-l-glycidylhydantoin-3-yl)propane, or any combination thereof.
  • a prereacted adduct of such epoxy resin with a hardener is suitable for epoxy resin.
  • a mixture of epoxy constituents may also be used in the binder formulation.
  • an epoxy constituent includes cycloaliphatic diepoxide.
  • An exemplary cycloaliphatic diepoxide is bis(4-hydroxycyclohexyl)methane diglycidyl ether, 2,2-bis(4-hydroxycyclohexyl)propane diglycidyl ether, 3,4-epoxycyclohexylmethyl-3,4- epoxycyclohexanecarboxylate, 3 ,4-epoxy-6-methylcyclohexylmethyl-3 ,4-epoxy-6- methylcyclohexanecarboxylate, di(3,4-epoxycyclohexylmethyl)hexanedioate, di(3,4-epoxy-6- methylcyclohexylmethyl)hexanedioate, ethylenebis(3,4-epoxycyclohexanecarboxylate), ethanedioldi(3 ,4-e ⁇ oxycyclohexylmethyl) ether
  • the epoxy constituent can have a molecular weight that varies over a wide range.
  • the epoxy equivalent weight i.e., the number average molecular weight divided by the number of reactive epoxy groups, is preferably in the range of 60 to 1000.
  • the binder formulation includes from about 10% to about 90% by weight of the epoxide constituent. Weight percentages of constituents of the binder formulation are stated relative to the total weight of the curable components of the composition, unless specified otherwise.
  • the binder formulation may include another cationically curable component, such as a cyclic ether component, a vinyl ether component, a cyclic lactone component, a cyclic acetal component, a cyclic thioether component, a spiro orthoester component, an oxetane- functional component, or any combination thereof.
  • a cyclic ether component such as a vinyl ether component, a cyclic lactone component, a cyclic acetal component, a cyclic thioether component, a spiro orthoester component, an oxetane- functional component, or any combination thereof.
  • an oxetane is a component comprising one or more oxetane groups, i.e. one or more four-member ring structures according to formula (5):
  • the binder formulation may also include a cationic photoinitiator.
  • a cationic photoinitiator that, upon exposure to actinic radiation, forms cations that initiate reactions of the epoxy constituents can be used.
  • a photoinitiator includes, for example, an onium salt with anions of weak nucleophilicity.
  • An example includes halonium salt, iodosyl salt or sulfonium salt, such as are described in published European patent application EP 153904 and WO 98/28663, sulfoxonium salt, such as described, for example, in published European patent applications EP 35969, 44274, 54509, and 164314, diazonium salt, such as described, for example, in U.S. Pat.
  • Another cationic photoinitiator includes metallocene salt, such as described, for example, in published European applications EP 94914 and 94915.
  • An additional suitable onium salt initiator or metallocene salt can be found in "UV Curing, Science and Technology", (Editor S. P. Pappas, Technology Marketing Corp., 642 Westover Road, Stamford, Conn., U.S.A.) Or “Chemistry & Technology of UV & EB Formulation for Coatings, Inks & Paints", Vol. 3 (edited by P. K. T. Oldring).
  • a cationic photoinitiator includes a compound of formula I, II or III below,
  • Rl, R2, R3, R4, R5, R6, and R7 are, independent of each other, a C6-C18 aryl-group that may be unsubstituted or substituted by suitable radicals;
  • L is boron, phosphorus, arsenic, or antimony;
  • Q is a halogen atom or some of the radicals Q in an anion LQ m " may also be a hydroxy group; and
  • m is an integer that corresponds to the valence of L plus 1.
  • An example of a C6-C18 aryl group includes a phenyl, a naphthyl, an anthryl, or a phenanthryl group.
  • a suitable radical includes alkyl, for example, C1-C6 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, or various pentyl or hexyl isomers; alkoxy, for example, C1-C6 alkoxy, such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, or hexyloxy; alkylthio, such as C1-C6 alkylthio, such as methylthio, ethylthio, propylthio, butylthio, pentylthio, or hexylthio; halogen, such as fluorine, chlorine, bromine, or iodine; amino; cyano; nitro; arylthio, such as phenylthio; or any combination thereof.
  • alkoxy for
  • An example of a halogen atom Q includes chlorine or fluorine.
  • An anion LQ m " may include BF 4 " , PF 6 " , AsFi, SbF 6 " , SbF 5 (OH) " , or any combination thereof.
  • the photoinitiator includes a compound of formula III wherein R5, R6, and R7 are aryl, such as phenyl, biphenyl, or any combination thereof.
  • the photoinitiator includes a compound of formula (IV)
  • pi-arene or an anion of pi-arene is found in published European patent application EP 94915.
  • An additional example of a pi-arene includes toluene, xylene, ethylbenzene, cumene, methoxybenzene, methylnaphthalene, pyrene, perylene, stilbene, diphenylene oxide, diphenylene sulfide, or any combination thereof.
  • the pi-arene is cumene, methylnaphthalene, or stilbene.
  • An example of a nonnucleophilic anion X- includes FSO 3 " , an anion of an organic sulfonric acid or of a carboxylic acid; or an anion LQ m " , as defined above.
  • an anion may be derived from a partially fluoro or perfluoroaliphatic or a partially fluoro or a perfluoro aromatic carboxylic acid, or in particular, from a partially fluoro or perfluoroaliphatic or a partially fluoro or perfluoroaromatic organic sulfonic acid, or is an anion LQ m " .
  • a further example of an anion X " includes BF 4 " , PF 6 “ , AsF 6 “ , SbF 6 “ , SbF 5 (OH) “ , CF 3 SO 3 “ , C 2 F 3 SO 3 “ , n-C 3 F 7 SO 3 " , n-C 4 F 9 SO 3 " , n-C 6 F 13 SO 3 - , n-C 8 F 17 SO 3 " , C 6 F 5 SO 3 " , phosphorus tungstate, silicon tungstate, or any combination thereof.
  • an anion is PF 6 " , AsF 6 “ , SbF 6 “ , CF 3 SO 3 “ , C 2 F 3 SO 3 “ , n-C 3 F 7 SO 3 “ , n-C 4 F 9 SO 3 " , n-C 6 Fi 3 SO 3 “ , n-C 8 Fi 7 SO 3 " , or any combination thereof .
  • a metallocene salt can also be used in combination with an oxidizing agent. Such a combination is described in published European patent application EP 126712.
  • the binder formulation includes from about 0.1 wt% to about 20 wt%, such as about 0.2 wt% to about 10 wt%, of cationic photoinitiator, based on the total weight of the binder formulation.
  • a sensitizer may be used, depending on the type of initiator.
  • An exemplary sensitizer includes a polycyclic aromatic hydrocarbon, an aromatic keto compound, or any combination thereof. A specific example of a sensitizer is mentioned in published European patent application EP 153904.
  • An exemplary sensitizer includes benzoperylene, 1,8- diphenyl-l,3,5,7-octatetraene, or l,6-diphenyl-l,3,5-hexatriene, as described in U.S. Pat. No. 5,667,937.
  • An additional factor in the choice of sensitizer is the nature and primary wavelength of the source of actinic radiation.
  • the binder formulation may include a radically polymerizable constituent.
  • the binder formulation may include a compound having at least one ethylenic unsaturation which can be polymerized with radicals.
  • An example of a suitable ethylenic unsaturation is a group, such as acrylate, methacrylate, styrene, vinylether, vinyl ester, N-substituted acrylamide, N-vinyl amide functionalities, maleate ester, fumarate ester, or any combination thereof.
  • the ethylenic unsaturation is provided by a group containing acrylate, methacrylate, N-vinyl, or styrene functionality.
  • the binder formulation may include one or more compounds having one or more (meth)acrylate functionalities.
  • the free-radical polymerizable acrylic material that may be used in the binder formulation has, on average, at least one acrylic group which can be either the free acid or an ester.
  • (meth)acrylate is meant an acrylate, methacrylate, or any combination thereof.
  • An acrylic material typically undergoes a polymerization or a crosslinking reaction initiated by a free radical.
  • the acrylic material can be a monomer, an oligomer, a polymer, or any combination thereof. Typically, the acrylic material is a monomer or an oligomer.
  • An acrylic constituent includes, for example, diacrylate of cycloaliphatic or aromatic diol, such as 1,4-dihydroxymethylcyclohexane, 2,2-bis(4-hydroxycyclohexyl)propane, 1,4- cyclohexanedimethanol, bis(4-hydroxycyclohexyl)methane, hydroquinone, 4,4- dihydroxybiphenyl, bisphenol A, bisphenol F, bisphenol S, ethoxylated or propoxylated bisphenol A, ethoxylated or propoxylated bisphenol F, or ethoxylated or propoxylated bisphenol S, and any combination thereof.
  • diacrylate of cycloaliphatic or aromatic diol such as 1,4-dihydroxymethylcyclohexane, 2,2-bis(4-hydroxycyclohexyl)propane, 1,4- cyclohexanedimethanol, bis(4-hydroxycyclohexyl)methane, hydroquinone, 4,
  • a useful aromatic tri(meth)acrylate includes, for example, a reaction product of triglycidyl ether of trihydric phenol, or phenol or cresol novolac having three hydroxy groups with (meth)acrylic acid.
  • the acrylic material includes 1,4- dihydroxymethyl-cyclohexane diacrylate, bisphenol A diacrylate, ethoxylated bisphenol A diacrylate, or any combination thereof.
  • the binder formulation may include an acrylate of bisphenol A diepoxide, such as Ebecryl 3700® from UCB Chemical Corporation, Smyrna, Ga., a mixed acrylate/epoxy compound of bisphenol A such as Ebecryl 3605®, or an acrylate of 1,4-cyclohexanedimethanol.
  • an acrylate of bisphenol A diepoxide such as Ebecryl 3700® from UCB Chemical Corporation, Smyrna, Ga.
  • a mixed acrylate/epoxy compound of bisphenol A such as Ebecryl 3605®
  • an acrylate of 1,4-cyclohexanedimethanol such as 1,4-cyclohexanedimethanol.
  • a poly(meth)acrylate having functionality of greater than 2, where appropriate, may be used in the binder formulation.
  • Such a poly(meth)acrylate can be, for example, a tri, tetra, or pentafunctional monomeric or oligomeric aliphatic (meth)acrylate.
  • a suitable aliphatic polyfunctional (meth)acrylate includes, for example, a triacrylate or a trimethacrylate of hexane-2,4,6-triol, glycerol, or 1,1,1-trimethylolpropane; ethoxylated or propoxylated glycerol; or 1,1,1-trimethylolpropane or a hydroxy group-containing tri(meth)acrylate which is obtained by the reaction of triepoxy compound, such as, for example, triglycidyl ether of the mentioned triol, with (meth)acrylic acid.
  • triepoxy compound such as, for example, triglycidyl ether of the mentioned triol
  • pentaerythritol tetra-acrylate bistrimethylolpropane tetra-acrylate, pentaerythritol monohydroxytri(meth)acrylate, or dipentaerythritol monohydroxypenta(meth)acrylate, or any combination thereof may be useful.
  • hexafunctional urethane (meth)acrylate is useful.
  • urethane (meth)acrylate can be, for example, prepared by reacting a hydroxy-terminated polyurethane with acrylic acid or methacrylic acid, or by reacting an isocyanate-terminated prepolymer with hydroxyalkyl (meth)acrylate to follow the urethane (meth)acrylate.
  • an acrylate or a methacrylate such as tris(2-hydroxyethyl)isocyanurate triacrylate.
  • the amount of radically polymerizable constituent is, for example, between about 0.1 wt% and about 60 wt%, such as between about 5 wt% and about 60 wt% or between about 10 wt% and about 40wt %.
  • the binder formulation may include a radical initiator, such as a radical photoinitiator, especially in combination with radically polymerizable constituent.
  • a photoinitiator that forms free radicals when irradiated can be used.
  • Typical a photoinitiator includes benzoin, such as benzoin; benzoin ether, such as benzoin methyl ether, benzoin ethyl ether, or benzoin isopropyl ether; benzoin phenyl ether; benzoin acetate; acetophenone, such as acetophenone, 2,2-dimethoxyacetophenone, 4-(phenylthio)acetophenone, or 1,1-dichloroacetophenone; benzyl; benzil ketal, such as benzil dimethyl ketal, or benzil diethyl ketal; anthraquinones, such as 2-methylanthraquinone, 2-ethylanthraquinone, 2-
  • a suitable free-radical photoinitiator alternatively includes acetophenone, such as 2,2- dialkoxybenzophenone; a 1-hydroxyphenyl ketone, for example 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-l- ⁇ 4-(2-hydroxyethoxy)phenyl ⁇ -2-methyl-l-propanone, or 2- hydroxyisopropyl phenyl ketone (also called 2-hydroxy-2,2-dimethylaceto- phenone), or 1- hydroxycyclohexyl phenyl ketone.
  • Another class of free-radical photoinitiators comprises a benzil ketal, such as, for example, benzil dimethyl ketal.
  • An alpha-hydroxyphenyl ketone, benzil dimethyl ketal, or 2,4,6- trimethylbenzoyldiphenylphosphine oxide is also useful as a photoinitiator.
  • Another class of suitable free radical photoinitiators includes an ionic dye-counter ion compound, which is capable of absorbing actinic rays and producing free radicals that can initiate the polymerization of an acrylate.
  • an ionic dye-counter ion compound can thus cure using visible light in an adjustable wavelength range of 400 to 700 nanometers.
  • An additional ionic dye-counter ion compound and its mode of action are, for example, found in European patent application EP 223587 or U.S. Pat. Nos. 4,751,102, 4,772,530 or 4,772,541.
  • a further example of an ionic dye-counter ion compound includes an anionic dye-iodonium ion complexe, an anionic dye-pyryllium ion complexe or a cationic dye-borate anion compound of the following formula:
  • R13 R15 wherein D + is a cationic dye and R12, R13, R14, and R15 are, each independently of the others, alkyl, aryl, alkaryl, allyl, aralkyl, alkenyl, alkynyl, an alicyclic or saturated or unsaturated heterocyclic group.
  • R12 to Rl 5 can be found, for example, in published European patent application EP 223587.
  • the binder formulation may include about 0.01 wt% to about 20 wt% of free-radical photoinitiator, such as about 0.01 wt% to about 15 wt% of free- radical photoinitiator, based on the total weight of the composition.
  • a hydroxyl-group containing material may be used in the binder formulation.
  • the hydroxyl-group material may include liquid organic material having a hydroxyl functionality of at least 1, and preferably at least 2.
  • the hydroxyl-group material may be a liquid or a solid that is soluble or dispersible in the remaining components. Typically, the material is substantially free of a group that substantially slows down the curing reaction.
  • the organic material contains two or more primary or secondary aliphatic hydroxyl groups (i.e., the hydroxyl group is bonded directly to a non-aromatic carbon atom).
  • a monomer, an oligomer, or a polymer can be useful.
  • the hydroxyl equivalent weight i.e., the number average molecular weight divided by the number of hydroxyl groups, is typically in the range of 31 to 5000.
  • a representative example of a suitable organic material having a hydroxyl functionality of 1 includes alkanol, monoalkyl ether of polyoxyalkyleneglycol, monoalkyl ether of alkyleneglycol, or any combination thereof.
  • a representative example of a useful monomeric polyhydroxy organic material includes alkylene and arylalkylene glycol or polyol, such as 1,2,4-butanetriol, 1,2,6- hexanetriol, 1,2,3-heptanetriol, 2,6-dimethyl-l,2,6-hexanetriol, (2R,3R)-(-)-2-benzyloxy- 1,3,4-butanetriol, 1,2,3-hexanetriol, 1,2,3-butanetriol, 3-methyl-l,3,5-pentanetriol, 1,2,3- cyclohexanetriol, 1,3,5-cyclohexanetriol, 3,7,11,15-tetramethyl- 1,2 ,3-hexadecanetriol, 2- hydroxymethyltetrahydropyran-3 ,4,5-triol, 2,2,4,4-tetramethyl- 1 ,3 -cyclobutanediol, 1,3 - cyclopentanediol, trans- 1,
  • a representative example of a useful oligomeric or polymeric hydroxyl-containing material includes polyoxyethylene or polyoxypropylene glycol or triol of molecular weights from about 200 to about 10,000; polytetramethylene glycol of various molecular weights; copolymer containing pendant hydroxy groups formed by hydrolysis or partial hydrolysis of a vinyl acetate copolymer, polyvinylacetal resin containing pendant hydroxyl groups; hydroxy- terminated polyester or hydroxy-terminated polylactone; hydroxy-functionalized polyalkadiene, such as polybutadiene; aliphatic polycarbonate polyol, such as an aliphatic polycarbonate diol; hydroxy-terminated polyether, or any combination thereof.
  • a hydroxyl-containing monomer includes 1,4-cyclohexanedimethanol or aliphatic or cycloaliphatic monohydroxy alkanol, or any combination thereof.
  • a typical hydroxyl-containing oligomer or polymer includes a hydroxyl or a hydroxyl/epoxy functionalized polybutadiene, 1,4-cyclohexanedimethanol, polycaprolactone diol or triol, ethylene/butylene polyol, monohydroxyl functional monomer, or any combination thereof.
  • An example of polyether polyol is polypropylene glycol of various molecular weight or glycerol propoxylate-B-ethoxylate triol.
  • Another example includes a linear or a branched polytetrahydrofuran polyether polyol available in various molecular weights, such as for example 250, 650, 1000, 2000, and 2900 MW.
  • the binder formulation may include up to 60 wt % of polyol.
  • the binder formulation may include about 0.1 wt% to about 60 wt% polyol, such as between about 3 wt% and about 20 wt%.
  • the binder formulation includes a latent coloring component.
  • the latent coloring component forms a chromophore in response to curing of polymer constituent.
  • the latent coloring component forms color or changes color on contact with a photochemically generated photoacid.
  • the latent coloring component is a triaryl methane-, diphenyl methane-thiazine-, spiro-, lactam-, fluoran or isobenzofuranone-based color former.
  • triarylmethane-based color former includes 3-3-bis(p-dimethylaminopheny- l)-6- dimethylaminophthalide, 3 ,3 -bis(p-dimethylaminophenyl)phthalide, 3 -(p- dimethylaminophenyl)-3 -(1 ,2-dimethylindole-3 -yl)phthalide, 3 -(p-dimethylammophenyl)-3 -
  • a typical diphenylmethane-based latent colorant component includes 4,4'-bis- dimethylaminobenzhydryl benzyl ether, N-halophenyl-leucoauramine, N-2,4,5- trichlorophenyl-leucoauramine, or any combination thereof.
  • An exemplary thiazine-based color former includes benzoyl-leucomethylene blue, p-nitrobenzoyl-leucomethylene blue, or any combination thereof.
  • An exemplary spiro-based color former includes 3-methyl-spiro- dinaphthopyran, 3-ethyl-spiro-dinaphthopyran, 3-phenyl-spirodinapthopyran, 3-benzyl-spiro- dinaphthopyran, 3 -methyl-naphtho-(6'-methoxybenzo)spiropyran, 3 -propyl-spiro- dibenzopyran, or any combination thereof.
  • a lactam-based color former includes rhodamine- b-anilinolactam, rhodamine-(p-nitroanilino)lactam, rhodamine-(o-chloroanilino)lactam, or any combination thereof.
  • a fluoran-based color former includes 3,6-dimethoxyfluoran, 3,6- diethoxyfluoran, 3,6-dibutoxyfluoran, 3-dimethylamino-7-methoxyfluoran, 3-dimethylamino- 6-methoxylfluoran, 3-dimethylamino-7-methoxyfluoran, 3-diethylamino-7-chlorofluoran, 3- diethylamino-6-methyl-7-chlorofluoran, 3-diethylamino-6,7-dimethylfuoran, 3-(N-ethyl-p- toluidino)-7-methylfluoran, 3 -diethylamino-7-(N-acetyl-N-methylamino)fluoran, 3 - diethylamino-7-N-methylaminofluoran, 3-diethylamino-7-dibenzylaminofluoran, 3- diethylamino-5 -methyl-7-dibenz
  • Latent colorant components permitting the production of a wide range of colors are described, for example, by Peter Gregory in High-Technology Applications of Organic Colourants, Plenum Press, pages 124-134.
  • a latent coloring component includes an isobenzofuranone-based color former or a color former that is available under the tradenames of Copikem and Pergascript.
  • the latent colorant or latent coloring component may react with or change color in response to byproducts or chemical changes associated with curing of the binder formulation.
  • the latent colorant may change color in response to activation of a cationic photoinitiator.
  • the latent colorant may change color in response to a concentration of photoacid.
  • the latent colorant may change color in response to changes in concentration of monomeric constituents, solvents, or byproducts of the polymerization of monomers.
  • the latent colorant may change color in response to generation of cations or the concentration of cations, in particular, cations, such as H + cations, which may be expressed as pH in particular binder formulations and solvents.
  • the binder formulation includes between about 0.000 lwt% and about 2.0 wt%, such as about 0.0005 wt% to about 1.0 wt %, latent coloring component.
  • the binder formulation may also include a filler.
  • an inorganic substance is used and provided for water-resisting capabilities and mechanical properties.
  • An example of an inorganic filler includes silica, glass powder, alumina, alumina hydrate, magnesium oxide, magnesium hydroxide, barium sulfate, calcium sulfate, calcium carbonate, magnesium carbonate, silicate mineral, diatomaceous earth, silica sand, silica powder, titanium oxide, aluminum powder, bronze, zinc powder, copper powder, lead powder, gold powder, silver dust, glass fiber, titanic acid potassium whiskers, carbon whiskers, sapphire whiskers, verification rear whiskers, boron carbide whiskers, silicon carbide whiskers, silicon nitride whiskers, or any combination thereof.
  • the condition of the surface of the particles of the filler used and the impurities contained in filler from the manufacturing process can affect the curing reaction of the resin composition.
  • the filler particles may be washed with an appropriate primer.
  • the inorganic filler also may be surface-treated with a silane coupling agent.
  • An exemplary silane coupling agent includes vinyl triclorosilane, vinyl tris ( ⁇ -methoxyethoxy) silane, vinyltriethoxy silane, vinyltrimethoxy silane, r-(methacryloxypropyl)trimethoxy silane, ⁇ -(3,4-epoxycyclohexyl)ethyltrimethoxy silane, r-glycydoxypropyltrimethoxy silane, r- glycydoxypropylmethyl diethoxy silane, N- ⁇ -(aminoethyl)-r-aminopropyltrimethoxy silane, N- ⁇ -(aminoethyl)-.gamma.-aminopropylmetliyldimethoxy silane, r- aminopropyltriethoxysilane, N-phenyl-r-amino prop
  • the binder formulation includes about 0.01 wt% to about 95 wt % filler relative to the total weight of the composition.
  • the binder may include about 10 wt% to about 90 wt %, or about 20 wt% to about 80 wt % filler.
  • the particulate filler may be formed of inorganic particles, such as, for example, metals (such as, for example, steel, Au or Ag) or a metal complex, such as, for example, metal oxide, metal hydroxide, metal sulfide, metal halogen complex, metal carbide, metal phosphate, inorganic salt (like, for example, CaCOs), ceramics, or any combination thereof.
  • metals such as, for example, steel, Au or Ag
  • a metal complex such as, for example, metal oxide, metal hydroxide, metal sulfide, metal halogen complex, metal carbide, metal phosphate, inorganic salt (like, for example, CaCOs), ceramics, or any combination thereof.
  • An example of a metal oxide includes ZnO, CdO, SiO 2 , TiO 2 , ZrO 2 , CeO 2 , SnO 2 , MoO 3 , WO 3 , Al 2 O 3 , In 2 O 3 , La 2 O 3 , Fe 2 O 3 , CuO, Ta 2 O 5 , Sb 2 O 3 , Sb 2 O 5 , or any combination thereof.
  • a mixed oxide containing different metals may also be present.
  • the nanoparticle for example, may comprise a particle selected from the group consisting of ZnO, SiO 2 , TiO 2 , ZrO 2 , SnO 2 , Al 2 O 3 , co-formed silica alumina, or any combination thereof.
  • the nanometer sized particle may also have an organic component, such as, for example, carbon black, highly crosslinked/core shell polymer nanoparticle, or an organically modified nanometer-size particle, or any combination thereof.
  • an organic component such as, for example, carbon black, highly crosslinked/core shell polymer nanoparticle, or an organically modified nanometer-size particle, or any combination thereof.
  • Such a filler is described in, for example, US 6,467,897 and WO 98/51747, hereby incorporated by reference.
  • Particulate filler formed via a solution-based processes such as sol-formed or a sol-gel formed ceramic
  • a suitable sol is commercially available.
  • a colloidal silica in aqueous solution is commercially available under such trade designations as "LUDOX” (E.I. DuPont de Nemours and Co., Inc. Wilmington, Del.), "NYACOL” (Nyacol Co., Ashland, Ma.) or “NALCO” (Nalco Chemical Co., Oak Brook, 111.).
  • Many commercially available sols are basic, being stabilized by alkali, such as sodium hydroxide, potassium hydroxide, or ammonium hydroxide.
  • a well-suited particle includes sol-formed silica and sol-formed alumina.
  • the sol can be functionalized by reacting one or more appropriate surface-treatment agents with the inorganic oxide substrate particle in the sol.
  • the particulate filler is sub-micron sized.
  • the particulate filler may be a nano-sized particulate filler, such as a particulate filler having an average particle size about 3 to 500 nm.
  • the particulate filler has an average particle size about 3 nm to about 200 nm, such as about 3 nm to about 100 nm, about 3 nm to about 50 nm, about 8 nm to about 30 nm, or about 10 nm to about 25 nm.
  • the average particle size is not greater than about 500 nm, such as not greater than about 200 nm, less than about 100 nm, or not greater than about 50 nm.
  • the average particle size may be defined as the particle size corresponding to the peak volume fraction in a small-angle neutron scattering (SANS) distribution curve or the particle size corresponding to 0.5 cumulative volume fraction of the SANS distribution curve.
  • SANS small-angle neutron scattering
  • the particulate filler may also be characterized by a narrow distribution curve having a half-width not greater than about 2.0 times the average particle size.
  • the half- width may be not greater than about 1.5 or not greater than about 1.0.
  • the half-width of the distribution is the width of the distribution curve at half its maximum height, such as half of the particle fraction at the distribution curve peak.
  • the particle size distribution curve is mono-modal.
  • the particulate filler is generally dispersed in an external phase. Prior to curing, the particulate filler is colloidally dispersed within the binder formulation and forms a colloidal composite binder once cured. For example, the particulate material may be dispersed such that Brownian motion sustains the particulate filler in suspension.
  • the particulate filler is substantially free of particulate agglomerates.
  • the particulate filler may be substantially mono-disperse such that the particulate filler is dispersed as single particles, and in particular examples, has only insignificant particulate agglomeration, if any.
  • the particles of the particulate filler are substantially spherical.
  • the particles may have a primary aspect ratio greater than 1, such as at least about 2, at least about 3, or at least about 6, wherein the primary aspect ratio is the ratio of the longest dimension to the smallest dimension.
  • the particles may also be characterized by a secondary aspect ratio defined as the ratio of orthogonal dimensions in a plane generally perpendicular to the longest dimension.
  • the particles may be needle-shaped, such as having a primary aspect ratio at least about 2 and a secondary aspect ratio not greater than about 2, such as about 1.
  • the particles may be platelet-shaped, such as having a primary aspect ratio at least about 2 and a secondary aspect ratio at least about 2.
  • the particulate filler is prepared in an aqueous solution and mixed with the external phase of a suspension.
  • the process for preparing such suspension includes introducing an aqueous solution, such as an aqueous silica solution; polycondensing the silicate, such as to a particle size of 3 nm to 50 run; adjusting the resulting silica sol to an alkaline pH; optionally concentrating the sol; mixing the sol with constituents of the external fluid phase of the suspension; and optionally removing water or other solvent constituents from the suspension.
  • an aqueous silicate solution is introduced, such as an alkali metal silicate solution (e.g.
  • a sodium silicate or potassium silicate solution with a concentration in the range between 20% and 50% by weight based on the weight of the solution.
  • the silicate is then polycondensed to a particle size of from 3 nm to 50 nm, for example, by treating the alkali metal silicate solution with acidic ion exchangers.
  • the resulting silica sol is adjusted to an alkaline pH (e.g. pH>8) to stabilized against further polycondensation or agglomeration of existing particles.
  • the sol can be concentrated, for example, by distillation, typically to Si ⁇ 2 concentration of about 30% to about 40% by weight.
  • the sol is mixed with constituents of the external fluid phase. Thereafter, water or other solvent constituents are removed from the suspension.
  • the suspension is substantially water-free.
  • the fraction of the non-filler constituents in the pre-cured binder formulation, generally including the organic polymeric constituents, as a proportion of the binder formulation can be about 20% to about 95% by weight, for example, about 30% to about 95% by weight, and typically from about 50% to about 95% by weight, and even more typically from about 55% to about 80% by weight.
  • the fraction of the dispersed particulate filler phase can be about 5% to about 80% by weight, for example, about 5% to about 70% by weight, typically from about 5% to about 50% by weight, and more typically from about 20% to about 45% by weight.
  • colloidally dispersed and submicron particulate fillers described above are particularly useful in concentrations at least about 5 wt%, such as at least about 10 wt%, at least about 15 wt%, at least about 20 wt%, or as great as 40 wt% or higher.
  • the solution formed nanocomposites exhibit low viscosity and improved processing characteristics at higher loading.
  • the amounts of components are expressed as weight % of the component relative to the total weight of the composite binder formulation, unless explicitly stated otherwise.
  • the binder formulation including an external phase comprising polymeric or monomeric constituents and optionally including dispersed particulate filler may be used to form a make coat, size coat, compliant coat, or back coat of a coated abrasive article.
  • the binder formulation is coated on a backing, abrasive grains are applied over the make coat, and the make coat is cured.
  • a size coat may be applied over the make coat and abrasive grains.
  • the binder formulation is blended with the abrasive grains to form abrasive slurry that is coated on a backing and cured.
  • the abrasive slurry is applied to a mold, such as injected into a mold and cured to form a bonded abrasive article.
  • the abrasive grains may be formed of any one of or a combination of abrasive grains, including silica, alumina (fused or sintered), zirconia, zirconia/alumina oxide, silicon carbide, garnet, diamond, cubic boron nitride, silicon nitride, ceria, titanium dioxide, titanium diboride, boron carbide, tin oxide, tungsten carbide, titanium carbide, iron oxide, chromia, flint, emery, or any combination thereof.
  • the abrasive grains may be selected from a group consisting of silica, alumina, zirconia, silicon carbide, silicon nitride, boron nitride, garnet, diamond, cofused alumina zirconia, ceria, titanium diboride, boron carbide, flint, emery, alumina nitride, or a blend thereof.
  • Particular embodiments have been created by use of dense abrasive grains comprised principally of alpha-alumina.
  • the abrasive grain may also have a particular shape. Examples of such shapes include rods, triangles, pyramids, cones, solid spheres, hollow spheres and the like. Alternatively, the abrasive grain may be randomly shaped.
  • the abrasive grains generally have an average grain size not greater than 2000 microns, such as not greater than about 1500 microns. In another example, the abrasive grain size is not greater than about 750 microns, such as not greater than about 350 microns.
  • the abrasive grain size may be at least 0.1 microns, such as from about 0.1 microns to about 1500 micron, and more typically from about 0.1 microns to about 200 microns or from about 1 micron to about 100 microns.
  • the grain size of the abrasive grains is typically specified to be the longest dimension of the abrasive grain. Generally, there is a range distribution of grain sizes. In some instances, the grain size distribution is tightly controlled.
  • the abrasive grains provide from about 10% to about 90%, such as from about 30% to about 80%, of the weight of the abrasive slurry.
  • the abrasive slurry may further include a grinding aid to increase the grinding efficiency and cut rate.
  • a grinding aid can be inorganic based, such as halide salts, for example sodium cryolite, potassium tetrafluoroborate, etc.; or organic based, such as chlorinated waxes, for example, polyvinyl chloride.
  • a particular embodiment includes cryolite and potassium tetrafluoroborate with particle size ranging from 1 micron to 80 microns, and most typically from 5 microns to 30 microns.
  • the weight percent of grinding aid ranges is generally not greater than about 50 wt%, such as from about 0 wt% to about 50 wt%, and most typically from about 10 wt% to about 30 wt% of the entire slurry (including the abrasive grains).
  • FIG. 1 illustrates an exemplary embodiment of a coated abrasive article 100, which includes abrasive grains 106 secured to a backing or support member 102.
  • the abrasive grains 106 are secured to the backing 102 by a make coat 104.
  • the make coat 104 includes a binder, which is typically formed of a cured binder formulation including latent colorant. When the binder formulation is cured the latent colorant reacts to form reaction activated chromophores that impart color to the binder or change the color of the binder.
  • the coated abrasive article 100 may further include a size coat 108 overlying the make coat 104 and the abrasive grains 106.
  • the size coat 108 generally functions to further secure the abrasive grains 106 to the backing 102 and may also provide grinding aids.
  • 108 is generally formed from a cured binder formulation that may be the same or different from the make coat binder formulation and may include a second latent colorant.
  • the coated abrasive 100 may also, optionally, include a back coat 112.
  • the back coat 112 functions as an anti-static layer, preventing abrasive grains from adhering to the back side of the backing 102 and preventing swarf from accumulating charge during sanding.
  • the back coat 112 may provide additional strength to the backing 102 and may act to protect the backing 102 from environmental exposure.
  • the back coat 112 can also act as a compliant layer. The compliant layer may act to relieve stress between the make coat 104 and the backing 102.
  • the backing may be flexible or rigid.
  • the backing may be made of any number of various materials including those conventionally used as backings in the manufacture of coated abrasives.
  • An exemplary flexible backing includes a polymeric film (including primed film), such as polyolefin film (e.g., polypropylene including biaxially oriented polypropylene), polyester firm (e.g., polyethylene terephthalate), polyamide film, cellulose ester film, metal foil, mesh, foam (e.g., natural sponge material or polyurethane foam), cloth (e.g., cloth made from fibers or yams comprising polyester, nylon, silk, cotton, poly-cotton or rayon), paper, vulcanized paper, vulcanized rubber, vulcanized fiber, nonwoven materials, any combination thereof, or any treated version thereof.
  • polymeric film including primed film
  • polyolefin film e.g., polypropylene including biaxially oriented polypropylene
  • polyester firm e.g., polyethylene
  • a cloth backing may be woven or stitch bonded.
  • the backing is selected from a group consisting of paper, polymer film, cloth, cotton, poly-cotton, rayon, polyester, poly-nylon, vulcanized rubber, vulcanized fiber, metal foil, or any combination thereof.
  • the backing includes polypropylene film or polyethylene terephthalate (PET) film.
  • PET polyethylene terephthalate
  • the backing may, optionally, have at least one of a saturant, a presize layer or a backsize layer. The purpose of these layers is typically to seal the backing or to protect yarn or fibers in the backing. If the backing is a cloth material, at least one of these layers is typically used.
  • presize layer or backsize layer may additionally result in a "smoother" surface on either the front or the back side of the backing.
  • Other optional layers known in the art may also be used (e.g., tie layer; see, e.g., U.S. Pat. No. 5,700,302 (Stoetzel et al.), the disclosure of which is incorporated by reference).
  • An antistatic material may be included in any of the above cloth treatment materials.
  • the addition of an antistatic material can reduce the tendency of the coated abrasive article to accumulate static electricity when sanding wood or wood-like material. Additional details regarding antistatic backings and backing treatments can be found in, for example, U.S. Pat. Nos. 5,108,463 (Buchanan et al.); 5,137,542 (Buchanan et al.); 5,328,716 (Buchanan); and 5,560,753 (Buchanan et al.), the disclosures of which are incorporated herein by reference.
  • the backing may be a fibrous reinforced thermoplastic, such as described, for example, in U.S. Pat. No. 5,417,726 (Stout et al.), or an endless spliceless belt, as described, for example, in U.S. Pat. No. 5,573,619 (Benedict et al.), the disclosures of which are incorporated herein by reference.
  • the backing may be a polymeric substrate having hooking stems projecting therefrom, such as that described, for example, in U.S. Pat. No.
  • the backing may be a loop fabric, such as that described, for example, in U.S. Pat.
  • a pressure-sensitive adhesive is incorporated onto the back side of the coated abrasive article such that the resulting coated abrasive article can be secured to a pad.
  • exemplary pressure-sensitive adhesives include latex crepe, rosin, acrylic polymer or copolymer, including polyacrylate ester (e.g., poly(butyl acrylate)), vinyl ether (e.g., polyvinyl n-butyl ether)), alkyd adhesive, rubber adhesives (e.g., natural rubber, synthetic rubber, chlorinated rubber), or any mixture thereof.
  • An exemplary rigid backing includes a metal plate, a ceramic plate, or the like. Another example of a suitable rigid backing is described, for example, in U.S. Pat. No. 5,417,726 (Stout et al.), the disclosure of which is incorporated herein by reference.
  • a coated abrasive article such as the coated abrasive article 100 of FIG. 1, may be formed by coating a backing with a binder formulation or abrasive slurry.
  • the backing may be coated with a compliant coat or back coat prior to coating with the make coat.
  • the binder formulation is applied to the backing to form the make coat.
  • abrasive grains are applied with the binder formulation, wherein the abrasive grains are blended with the binder formulation to form abrasive slurry prior to application to the backing.
  • the binder formulation is applied to the backing to form the make coat and the abrasive grains are applied to the make coat, such as through electrostatic and pneumatic methods.
  • the binder formulation is cured such as through thermal methods or exposure to actinic radiation, causing a color change in the latent colorant.
  • a size coat is applied over the make coat and abrasive grains.
  • the size coat may be applied prior to curing the make coat, the make coat and size coat being cured simultaneously.
  • the make coat is cured prior to application of the size coat and the size coat is cured separately.
  • Latent colorants in the size coat may change color during curing.
  • the binder formulation forming the make coat, the size coat, the compliant coat or the back coat may include colloidal binder formulation.
  • the colloidal binder formulation may include sub-micron particulate filler, such as nano-sized particulate filler having a narrow particle size distribution.
  • the colloidal binder formulation is cured to form the size coat.
  • the colloidal binder fonnulation is cured to form the make coat.
  • the colloidal binder formulation may be cured to form the optional compliant coat or the optional back coat.
  • the coats and abrasive grains may be patterned to form structures.
  • the make coat may be patterned to form surface structures that enhance abrasive article performance. Patterns may be pressed or rolled into the coats using, for example, a rotogravure apparatus to form a structured or engineered abrasive article.
  • the structured abrasive includes a backing 202 and a layer 204 including abrasive grains.
  • the backing 202 may be formed of the materials described above in relation to the backing 102 of FIG. 1.
  • the layer 204 is patterned to have surface structures 206.
  • the layer 204 may be formed as one or more coats.
  • the layer 204 may include a make coat and optionally, a size coat.
  • the layer 204 generally includes abrasive grains and a binder.
  • the abrasive grains are blended with a binder formulation to form an abrasive slurry.
  • the abrasive grains are applied to the binder after the binder is coated on the backing 202.
  • a functional powder may be applied over the layer 204 to prevent the layer 204 from sticking to the patterning tooling.
  • the binder of the make coat or the size coat may include latent colorant.
  • the structured abrasive article 200 optionally may include compliant and back coats (not shown). These coats may function as described above.
  • a binder formulation including latent colorant may be used to form bonded abrasive articles, such as the abrasive article 300 illustrated in FIG. 3.
  • binder formulation and abrasive grains are blended to form abrasive slurry.
  • the abrasive slurry is applied to a mold and the binder formulation is cured, causing a change in color of the latent colorant.
  • the resulting abrasive article, such as article 300 includes the abrasive grains bound by nano-composite binder in a desired shape.
  • the abrasive article is formed by blending nanocomposite precursors with other polymeric precursors and constituents.
  • a nanocomposite epoxy precursor including nano-sized particulate filler and epoxy precursor, is mixed with acrylic precursor to form a nanocomposite binder formulation.
  • the binder formulation is applied to a substrate, such as a backing or to a mold. Abrasive grains are also applied to the substrate and the binder formulation is cured.
  • the nanocomposite binder formulation may be applied to a backing and abrasive grains applied over the formulation.
  • the binder formulation may be applied over the abrasive grains to form a size coat.
  • the binder formulation and the abrasive grains may be blended and applied simultaneously to form a make coat over a substrate or to fill a mold.
  • the binder formulation may be cured using thermal energy or actinic radiation, such as ultraviolet radiation.
  • the binder formulation includes an epoxy constituent, a cationic photoinitiator within the epoxy constituent, and a latent colorant configured to change color in response to activation of the cationic photoiniator.
  • the binder formulation may include about 10 wt% to about 90 wt%, such as about 65 wt% to about 80 wt%, of the epoxy constituent and may include about 0.1 wt% to about 20 wt%, such as about 0.1 wt% to about 4.0 wt%, of the cationic photoinitiator.
  • the epoxy constituent may include nano-sized particulate filler, such as filler having particle size not greater than about 100 nm, such as not greater than about 50 nm.
  • the binder formulation may include an acrylic constituent and a radical generating photoinitiator.
  • the binder formulation may include about 0.1 wt% to about 60 wt%, such as about 5 wt% to about 15 wt%, of the acrylic constituent and may include about 0.01 wt% to about 20 wt%, such as about 0.1 wt% to about 4 wt%, radical generating photoinitiator.
  • the acrylic constituent may include nano-sized particulate filler, such as filler having particle size not greater than about 100 run, such as not greater than about 50 nm.
  • the binder formulation may also include a polyol constituent in an amount of about 0.1 wt% to about 60 wt%, such as about 10 wt% to about 17 wt%.
  • the latent colorant may exhibit a specific color based on curing of the epoxy constituent.
  • the latent colorant reacts with byproducts of the cationic photoinitiator to change color.
  • the binder formulation may include one or more colorants.
  • the binder formulation may further include a second latent colorant.
  • the second latent colorant may change to a second color based on the curing.
  • the second colorant changes color in response to a different reaction, such as activation of a radical generating photoinitiator.
  • the latent colorant and the second latent colorant may together change to appear as a desirable color.
  • a first reaction activated chromophore associated with the first latent colorant may have a first electromagnetic energy absorption profile and a second reaction activated chromophore associated with the second latent colorant may have a second electromagnetic energy absorption profile.
  • the first electromagnetic energy absorption profile is different from the second electromagnetic energy absorption profile.
  • the first electromagnetic energy absorption profile and the second electromagnetic energy absorption profile appear as a desired color.
  • a latent colorant may be selected for addition to a binder formulation to provide color coding of binder formulations.
  • a first binder formulation may include a first latent colorant and a second binder formulation may include a second latent colorant.
  • the color of a cured abrasive product may aid in identifying the binder formulation used to form the cured abrasive product.
  • each coat such as a make coat or a size coat, may be formed from a different binder formulation and each of the different binder formulations may include a different latent colorant.
  • the binder formulation may be cured to form an abrasive product, such as a layer of a coated abrasive product.
  • Latent colorants become chromophores through reactions associated with curing of the polymer components.
  • the latent colorants and chromophores are organic, not to be confused with inorganic pigments.
  • the binder formulation and resulting abrasive product are free of particulate pigment.
  • particulate pigment can interfere with curing through actinic radiation, causing defects in resulting abrasive products.
  • the disclosure is directed to a method of manufacturing an abrasive article.
  • the method includes initiating a curing process on a workpiece, determining a target color exhibited by the workpiece, and terminating the curing process based on the target color.
  • the target color may represent partial curing or full curing.
  • the curing process may include photo curing or thermal curing.
  • a make coat is applied to the abrasive article workpiece prior to curing.
  • an uncured size coat is applied to the workpiece prior to curing.
  • a mold is filled to form the workpiece.
  • a second curing process may be initiated after terminating the curing process, a second target color may be determined and the second curing process terminated based on the second target color.
  • the disclosure is directed to a method of controlling abrasive product quality.
  • the method includes forming an abrasive product having a polymer matrix and a reaction activated chromophore, inspecting the abrasive product for a color characteristic, and categorizing the abrasive product based on the color characteristic.
  • the color characteristic may, for example, be a target color or color uniformity.
  • Categorizing the abrasive product may include rejecting the abrasive product, accepting the abrasive product or grading the abrasive product. Grades may be associated with abrasive product usage conditions.
  • the product may be further cured after categorizing.
  • Measurement of color can be performed with a chromameter.
  • a chromameter provides three values in the L*a*b color scale (CEELAB).
  • the CIELAB color scale is an approximate uniform color scale. In a uniform color scale, the differences between points plotted in the color space correspond to visual differences between the colors plotted.
  • the CIELAB color space is organized in a cube form.
  • the L* axis runs from the top to bottom.
  • the maximum L* is 100, which represents a reflecting diffuser.
  • the minimum L* is zero, which represents black.
  • the a* and b* axis have no specific numerical limit. Positive a* is typically red and negative a* is typically green. Positive b* is generally yellow and negative b* is generally blue. For example, when a* is -60, it represents green and when a* is +60, it represents red. The b* represents blue when it is -60 and yellow when it is +60. Articles having a* and b* value between -20 and 20 typically have a grey appearance. Articles having a* and b* values between -20 and -60 or between 20 and 60 are generally more colorful. Typically, conventional resin compositions with and without fillers but without latent colorant exhibit large L* values of between 90 and 100.
  • embodiments of articles, for example, formed by UV-curing of a resin including latent colorant exhibit a different color than the uncured resin.
  • a color may be expressed as a change in L* value, a* value, or b* value relative to the resin.
  • the L* value may change at least about 10 units, such as at least about 20 units.
  • the a* or b* values of an article change by at least about 10 units after cure of the resin.
  • the a* or b* value may change by at least about 20 units.
  • the L* value may not change substantially, but the color may change, for example, from red to blue.
  • the a* or b* value may change at least about 20 units, such as at least about 30 units.
  • the L* value of the article changes relative to the resin, so that cured articles have L* values of between 0 and 85, such as between 20 and 75.
  • the a* or b* value of the cured articles may stay the same as the values of the resin when the L* value changes.
  • the L* value of a binder formulation or an abrasive article workpiece may change by at least about 10%, such as at least about 20% or at least about 30%.
  • the a* value or the b* value may change by at least about 10%, such as at least about 20% or at least about 30%.
  • the method may include dete ⁇ nining a target L* value or a change in L* value.
  • the method may include determining a target a* value or a target b* value or changes in the a* value or the b* value.
  • An example binder formulation includes:
  • Sample binder formulations are prepared and cured.
  • the color of the cured samples are tested using a HunterLab ColorQuest XE chromameter in reflectance test mode with a D65 illuminant and at an angle of 10°.
  • the color of the samples is represented in the CIELAB color scale.
  • a white backing medium is used during measurement.
  • Effect of dye concentration on binder color is determined by testing binder formulations in a standardized abrasive article configuration (4 inch length and 10 inch width).
  • the binder formulations at different dye concentrations are used as a size coat over abrasive grains and a make coat.
  • Film samples that have size coatings at different dye concentration are UV cured at 300W D bulb/600W H bulb at a line speed 50 feet/minute.
  • the abrasive grains are 80 micron heat-treated semi-friable aluminum oxide frommaschineacher (BFRPL) P 180 grit and the make coat is formed of UV-curable epoxy/acrylate resins.
  • the abrasive grains and make coat overlie a polyester backing.
  • Size coats on sample abrasive articles are formed from binder formulations including Nanopox XP A610 available from Hanse Chemie, an epoxy resin including 3,4-epoxy cyclohexyl methyl-3,4-epoxy cyclohexyl carboxylate and 40 wt% colloidal silica particulate filler.
  • the binder formulations also include UVR 6105, which includes 3, 4-epoxy cyclohexyl methyl-3,4-epoxy cyclohexyl carboxylate and no particulate filler.
  • the binder formulations further include a polyol (4,8-bis(hydroxymethyl) tricyclo(5.2.1.0)decane), a cationic photoinitiator (Chivacure 1176), a radical photoinitiator (Irgacure 2022, available from Ciba®), acrylate precursor (SR 399, a dipentaerythritol pentaacrylate available from Atofma-Sartomer, Exton, PA), and dye (specialty bluel, available from Noveon Hilton Davis, Inc., 2235 Langdon Farms Rd., Cincinnati, OH 45237- 4790).
  • a polyol 4,8-bis(hydroxymethyl) tricyclo(5.2.1.0)decane
  • Chivacure 1176 cationic photoinitiator
  • Irgacure 2022 available from Ciba®
  • acrylate precursor SR 399, a dipentaerythritol pentaacrylate available from Atofma-Sarto
  • Table 1 illustrates the concentration of components in the binder formulations and the resulting value of L*, a*, and b*.
  • increasing the concentration of Specialty Blue 1 dye causes a reduction in L* for the cured binder formulation, hi addition, b* changes in a negative direction with increasing Specialty Blue 1 dye in the binder formulation.
  • Exemplary embodiments of the above described binder formulations and abrasive articles formed from the binder formulation may advantageously be useful in quality control, end product coloration, characterization of the product, and process control. Absence of particulate pigments advantageously leads to improved curing for actinic radiation curable binder formulations.

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  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Polishing Bodies And Polishing Tools (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne un article abrasif ayant une couche incluant un constituant époxy, le constituant époxy contenant un photoinitiateur cationique et un colorant latent configuré de façon à changer de couleur en réponse à l'activation du photoinitiateur cationique.
EP06749490A 2005-04-08 2006-04-06 Article abrasif ayant un groupe chromophore active par une reaction Withdrawn EP1877224A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US66941305P 2005-04-08 2005-04-08
PCT/US2006/012991 WO2006110517A1 (fr) 2005-04-08 2006-04-06 Article abrasif ayant un groupe chromophore active par une reaction

Publications (1)

Publication Number Publication Date
EP1877224A1 true EP1877224A1 (fr) 2008-01-16

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EP06749490A Withdrawn EP1877224A1 (fr) 2005-04-08 2006-04-06 Article abrasif ayant un groupe chromophore active par une reaction

Country Status (8)

Country Link
US (1) US20060242910A1 (fr)
EP (1) EP1877224A1 (fr)
CN (1) CN101175607A (fr)
BR (1) BRPI0608938A2 (fr)
CA (1) CA2602891A1 (fr)
MX (1) MX2007012389A (fr)
TW (1) TWI321099B (fr)
WO (1) WO2006110517A1 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0612788D0 (en) * 2006-06-28 2006-08-09 Insectshield Ltd Pest control materials
US8083820B2 (en) * 2006-12-22 2011-12-27 3M Innovative Properties Company Structured fixed abrasive articles including surface treated nano-ceria filler, and method for making and using the same
EP2327088B1 (fr) * 2008-08-28 2019-01-09 3M Innovative Properties Company Article abrasif structuré, son procédé de fabrication et utilisation dans la planarisation de plaquettes
DE202009006069U1 (de) * 2009-04-27 2009-08-06 Schaum-Chemie Wilhelm Bauer Gmbh & Co. Kg Polierscheibe
JP5767325B2 (ja) * 2010-07-02 2015-08-19 スリーエム イノベイティブ プロパティズ カンパニー 被覆研磨材物品
CN108262695A (zh) * 2011-06-30 2018-07-10 圣戈本陶瓷及塑料股份有限公司 包括氮化硅磨粒的磨料制品
CN102643613B (zh) * 2012-03-31 2014-03-12 常州同泰光电有限公司 一种用于蓝宝石衬底的研磨液及其制备方法
DE102013103643B4 (de) 2013-04-11 2019-11-07 Lukas-Erzett Vereinigte Schleif- Und Fräswerkzeugfabriken Gmbh & Co. Kg Schleifwerkzeug und Verwendung eines Schleifwerkzeuges
TWI553153B (zh) * 2013-06-28 2016-10-11 聖高拜陶器塑膠公司 鍍鎳鑽石顆粒及其製造方法
DE102014216650A1 (de) * 2014-08-21 2016-02-25 Robert Bosch Gmbh System von Schleifwerkzeugen
EP3523376B1 (fr) * 2016-10-05 2022-04-20 AFI Licensing LLC Compositions de revêtement comprenant du diamant et des systèmes de résine durcissable cationique ou des systèmes durcissables thiol-ène
EP3732021A1 (fr) * 2017-12-29 2020-11-04 DSM IP Assets B.V. Compositions et articles pour l'impression 3d, et leurs procédés d'utilisation

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3114724A (en) * 1962-01-31 1963-12-17 Us Rubber Co Low temperature expansion of liquid organic polysulfide polymer with metal hydrides, borohydrides or aluminum hydrides
WO2000040635A1 (fr) * 1998-12-31 2000-07-13 3M Innovative Properties Company Compositions photo-polymerisables et articles fabriques a partir de celles-ci
US20040014396A1 (en) * 2002-07-18 2004-01-22 Elledge Jason B. Methods and systems for planarizing workpieces, e.g., microelectronic workpieces

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3708296A (en) * 1968-08-20 1973-01-02 American Can Co Photopolymerization of epoxy monomers
US5002846A (en) * 1985-10-30 1991-03-26 Xerox Corporation Developer compositions with coated carrier particles
US4772530A (en) * 1986-05-06 1988-09-20 The Mead Corporation Photosensitive materials containing ionic dye compounds as initiators
US4772541A (en) * 1985-11-20 1988-09-20 The Mead Corporation Photohardenable compositions containing a dye borate complex and photosensitive materials employing the same
US4751138A (en) * 1986-08-11 1988-06-14 Minnesota Mining And Manufacturing Company Coated abrasive having radiation curable binder
US4751102A (en) * 1987-07-27 1988-06-14 The Mead Corporation Radiation-curable ink and coating compositions containing ionic dye compounds as initiators
US5108463B1 (en) * 1989-08-21 1996-08-13 Minnesota Mining & Mfg Conductive coated abrasives
US5126394A (en) * 1989-10-18 1992-06-30 Dow Corning Corporation Radiation curable abrasion resistant coatings from colloidal silica and acrylate monomer
US5137542A (en) * 1990-08-08 1992-08-11 Minnesota Mining And Manufacturing Company Abrasive printed with an electrically conductive ink
US5316812A (en) * 1991-12-20 1994-05-31 Minnesota Mining And Manufacturing Company Coated abrasive backing
KR0161543B1 (ko) * 1991-12-20 1998-12-15 테릴 켄트 쿠알리 이음매 없는 순환 배킹을 갖는 코팅된 연마 벨트 및 이것을 제조하는 방법
CA2128089A1 (fr) * 1992-02-12 1993-08-19 Herbert W. Schnabel Abrasif applique comportant un support electriquement conducteur
US5328716A (en) * 1992-08-11 1994-07-12 Minnesota Mining And Manufacturing Company Method of making a coated abrasive article containing a conductive backing
AU683688B2 (en) * 1993-10-19 1997-11-20 Minnesota Mining And Manufacturing Company Abrasive articles comprising a make coat transferred by lamination
US5505747A (en) * 1994-01-13 1996-04-09 Minnesota Mining And Manufacturing Company Method of making an abrasive article
WO1996041237A1 (fr) * 1995-06-07 1996-12-19 E.I. Du Pont De Nemours And Company Sensibilisants et precurseurs photoacides
US5700302A (en) * 1996-03-15 1997-12-23 Minnesota Mining And Manufacturing Company Radiation curable abrasive article with tie coat and method
US6228133B1 (en) * 1998-05-01 2001-05-08 3M Innovative Properties Company Abrasive articles having abrasive layer bond system derived from solid, dry-coated binder precursor particles having a fusible, radiation curable component
US6265459B1 (en) * 1998-12-31 2001-07-24 3M Innovative Properties Company Accelerators useful for energy polymerizable compositions
US6467897B1 (en) * 2001-01-08 2002-10-22 3M Innovative Properties Company Energy curable inks and other compositions incorporating surface modified, nanometer-sized particles
US7501198B2 (en) * 2002-02-07 2009-03-10 Linvatec Corporation Sterile transfer battery container
US6803353B2 (en) * 2002-11-12 2004-10-12 Atofina Chemicals, Inc. Copper chemical mechanical polishing solutions using sulfonated amphiprotic agents

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3114724A (en) * 1962-01-31 1963-12-17 Us Rubber Co Low temperature expansion of liquid organic polysulfide polymer with metal hydrides, borohydrides or aluminum hydrides
WO2000040635A1 (fr) * 1998-12-31 2000-07-13 3M Innovative Properties Company Compositions photo-polymerisables et articles fabriques a partir de celles-ci
US20040014396A1 (en) * 2002-07-18 2004-01-22 Elledge Jason B. Methods and systems for planarizing workpieces, e.g., microelectronic workpieces

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO2006110517A1 *

Also Published As

Publication number Publication date
TW200706368A (en) 2007-02-16
BRPI0608938A2 (pt) 2010-02-17
CN101175607A (zh) 2008-05-07
WO2006110517A1 (fr) 2006-10-19
MX2007012389A (es) 2007-12-13
TWI321099B (en) 2010-03-01
US20060242910A1 (en) 2006-11-02
CA2602891A1 (fr) 2006-10-19

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