EP2195383A2 - Composition resinique liquide pour articles abrasifs - Google Patents

Composition resinique liquide pour articles abrasifs

Info

Publication number
EP2195383A2
EP2195383A2 EP08842341A EP08842341A EP2195383A2 EP 2195383 A2 EP2195383 A2 EP 2195383A2 EP 08842341 A EP08842341 A EP 08842341A EP 08842341 A EP08842341 A EP 08842341A EP 2195383 A2 EP2195383 A2 EP 2195383A2
Authority
EP
European Patent Office
Prior art keywords
composition according
resin
equal
less
resin composition
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Withdrawn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
EP08842341A
Other languages
German (de)
English (en)
French (fr)
Inventor
Alix Arnaud
Philippe Espiard
Sandrine Pozzolo
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 Abrasifs Technologie et Services SAS
Saint Gobain Abrasives Inc
Original Assignee
Saint Gobain Abrasifs Technologie et Services SAS
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 Abrasifs Technologie et Services SAS, Saint Gobain Abrasives Inc filed Critical Saint Gobain Abrasifs Technologie et Services SAS
Publication of EP2195383A2 publication Critical patent/EP2195383A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B24GRINDING; POLISHING
    • B24DTOOLS FOR GRINDING, BUFFING OR SHARPENING
    • B24D3/00Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents
    • B24D3/02Physical 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
    • B24D3/20Physical 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 and being essentially organic
    • B24D3/28Resins or natural or synthetic macromolecular compounds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B24GRINDING; POLISHING
    • B24DTOOLS FOR GRINDING, BUFFING OR SHARPENING
    • B24D3/00Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents
    • B24D3/34Physical 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
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/04Condensation polymers of aldehydes or ketones with phenols only
    • C08L61/06Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00Materials not provided for elsewhere
    • C09K3/14Anti-slip materials; Abrasives
    • C09K3/1436Composite particles, e.g. coated particles

Definitions

  • the present invention relates to a liquid resin composition suitable for use in the manufacture of abrasive articles, and to the resulting abrasive articles.
  • Abrasive articles in general contain a multitude of abrasive grains securely bonded to a carrier or to each other via a binder. These articles are widely used for the machining of various materials, especially in cutting, grinding, deburring and polishing operations.
  • abrasive coated abrasives and abrasive bonded abrasives are distinguished.
  • the abrasives applied comprise a support material, generally flexible, on the surface of which are distributed abrasive grains embedded in a binder.
  • the flexible support may be a sheet of paper, a film or a network of fibers, for example a mat, a felt, a fabric or a knit of natural or synthetic fibers, in particular made of glass or a polymer.
  • These abrasives can take various forms: sheets, strips, discs, etc.
  • the manufacture of the coated abrasives includes the application of a base coat ("make coat”) on the support material, the distribution of the grains of abrasives on said layer, the heat treatment of the base adhesive layer to partially cure it and the application of a top adhesive layer ("size coat”) which ensures a firm anchoring of the grains on the support.
  • a base coat (“make coat")
  • size coat a top adhesive layer which ensures a firm anchoring of the grains on the support.
  • An additional adhesive layer (“supersize coat”) may be deposited on the upper adhesive layer and the abrasive grains.
  • the base, top and extra adhesive layers are applied in liquid form. They are generally made of a thermosetting resin, in particular a phenolic resin of resol type.
  • the agglomerated abrasives consist of abrasive grains bonded together by a binder which provides a three-dimensional structure adapted to ensure the abrasion operations, including the cutting of hard materials such as steel. Generally, these abrasives have the appearance of a grinding wheel, a grinding wheel segment and a whetstone.
  • Agglomerated abrasives in the form of "conventional" grinding wheels consist of a single region composed of abrasive grains embedded in the binder which extends from the bore to the periphery of the grinding wheel.
  • the abrasion region is located in the periphery, in the form of a strip supported by a central core generally made of metal, and the abrasive grains consist of a very hard material, for example diamond or cubic boron nitride.
  • Agglomerated abrasives are obtained by the process using compression molding techniques, cold or hot.
  • cold compression molding (“CoId Molding
  • Compression the most widespread, the mixture of constituents of the abrasive, in granular form, is introduced into a mold, then a sufficient compressive force is applied, of the order of 15 to 25 N / mm 2 , for placing said mixture in the shape of the mold and ensuring that after extraction of the mold, the piece obtained (green part or "green item") has sufficient strength to be manipulated without losing its original shape.
  • the part is then heated in an oven at a temperature to crosslink the binder, this temperature depending on the nature of the binder used.
  • Hot compression molding achieves a higher compaction level than cold molding, which results in a smaller pore volume in the final article.
  • the granular mixture introduced into the mold is compacted under pressure and heated simultaneously in order to allow the binder to be better distributed between the abrasive grains and to occupy the empty spaces.
  • the part After being removed from the mold, the part generally undergoes a post-crosslinking heat treatment to improve its operating life and abrasion performance.
  • the granular mixture is prepared by pre-treating the abrasive grains with a liquid impregnating resin, usually a resol type phenolic resin, and then mixing the wet grains with a novolak type phenolic resin powder containing a crosslinking agent - powder which will subsequently constitute the binder itself - and optionally additives, also in powder form.
  • a liquid impregnating resin usually a resol type phenolic resin
  • a novolak type phenolic resin powder containing a crosslinking agent - powder which will subsequently constitute the binder itself - and optionally additives, also in powder form.
  • the resulting mixture thus consists of abrasive grains on the surface of which are adhered solid particles of resin and additives.
  • This mixture has a good ability to be uniformly distributed in the mold (called "flowability") and to be shaped under the effect of pressure.
  • thermosetting resins used for the manufacture of coated and agglomerated abrasives have numerous advantages in the intended use conditions, in particular: they ensure a solid connection of the grains with the support material and grains between them,
  • a disadvantage of the aforementioned resols is that they contain formaldehyde detrimental to human health and the environment.
  • the resols contain free formaldehyde which can be emitted into the atmosphere during the manufacture of the abrasives, and that they can further generate formaldehyde under the conditions of use of the abrasive, when the temperature reaches a level leading to the degradation of the resol with release of formaldehyde.
  • WO 2005/108454 A1 discloses a novolac resin and non-formaldehyde hardener composition for reinforcing composite materials.
  • a polymerizable abrasive composition which comprises an aminoplast resin and a reactive diluent which each contain pendant unsaturated groups.
  • US 5,178,646 discloses a binder precursor composition for abrasives, especially coated, which comprises a heat-curable resin having a plurality of pendant methylol groups and a reactive diluent having at least one functional group that reacts with the groups of the resin.
  • the present invention aims to reduce the amount of formaldehyde in an abrasive product.
  • the invention proposes a liquid resin composition which replaces the resole used as an adhesive in the coated abrasives and as an impregnating resin in the agglomerated abrasives, this liquid resin composition being characterized in that it comprises at least one novolak resin having a glass transition temperature of less than or equal to 60 ° C., at least one reactive diluent and optionally at least one crosslinking agent.
  • the novolac resin according to the invention is chosen from novolaks having a glass transition temperature of less than or equal to 60 ° C., preferably less than or equal to 50 ° C. and advantageously of between 35 ° and 45 ° C.
  • the novolak may be selected from novolacs known to those skilled in the art which are obtained by reaction of a phenolic compound and an aldehyde in an aldehyde / phenolic compound molar ratio of less than 1, in the presence of an acid catalyst.
  • the phenol compound is chosen from phenol and substituted phenols such as cresols, guaiacol, methoxyphenols, catechol, resorcinol, tert-butyl phenol and nonyl phenol, bisphenols such as bisphenol A, naphthols and mixtures of these compounds.
  • the phenol is selected.
  • the aldehyde is selected from alicyclic aldehydes such as formaldehyde, cyclic aldehydes such as furfural, aromatic aldehydes such as benzaldehyde, para-anisaldehyde, orthoaldehyde and the like. anisaldehyde and veratraldehyde, and mixtures of these aldehydes.
  • the formaldehyde is chosen.
  • the formaldehyde / phenol molar ratio ranges from 0.2 to less than 1, advantageously from 0.35 to 0.9, and more preferably from 0.5 to 0.9.
  • the novolak resin may be prepared using a known acidic catalyst, for example a strong mineral acid such as sulfuric acid, phosphoric acid and hydrochloric acid, or an organic acid such as oxalic acid, acid salicylic acid or anhydrides such as maleic anhydride.
  • the amount of acid should be sufficient to allow the condensation of the phenolic compound and the aldehyde.
  • the amount of acid used generally represents 0.02 and 1% of the weight of the starting phenolic compound, preferably 0.1 to 0.6% in the case of a strong mineral acid, and 0.3 to 3% of the weight of the starting phenolic compound in the case of an organic acid.
  • the novolac resin obtained at the end of the condensation reaction is treated so as to reduce the content of free phenolic compound, for example by distillation under reduced pressure.
  • the novolaks that can be used in the context of the invention contain less than 0.1% by weight of free formaldehyde, and preferably less than 0.05%.
  • the resin composition may comprise at least one resin capable of reacting with the crosslinking agent different from the novolac, for example an epoxy resin, in particular a novolac resin bearing one or more pendant epoxy groups.
  • Such epoxidized novolac resin may be obtained in conventional manner by treating a novolak resin with an excess of epichlorohydrin in the presence of a basic catalyst, e.g. sodium hydroxide, at a temperature of about 100 0 C.
  • the proportion of novolac resin according to the invention must however remain greater than or equal to 50% by weight of all the resins, novolac (s) and other (s), preferably greater than or equal to 75% and advantageously the proportion is equal to 100%.
  • the novolak resin according to the invention represents at least 30% by weight of the resin composition, preferably at least 40%, advantageously at least 50%, and does not exceed 85%.
  • the reactive diluent according to the invention is a liquid compound at ambient temperature, of the order of 20 to 25 ° C, which makes it possible to solubilize the novolak resin and to adjust the viscosity of the resin composition.
  • the reactive diluent has a viscosity of less than or equal to 1000 mPa.s, preferably less than or equal to 700 mPa.s, preferably less than 500 mPa.s and more preferably less than 350 mPa.s.
  • the reactive diluent also contains at least one function capable of reacting with the resin and optionally with the crosslinking agent, which function is chosen from the hydroxy, aldehyde, epoxy, oxazolidine and lactone functional groups.
  • reactive diluents comprising hydroxyl functional groups
  • alicyclic alcohols saturated or unsaturated, such as ethylene glycol, 1,3-butylene glycol, glycerol, trimethylolpropane and the monoallyl ethers of these cyclic, saturated or unsaturated alcohols, such as furfuryl alcohol, mono- or polynuclear aromatic alcohols such as benzyl alcohol and its derivatives, m-cresol, 3,5-xylenol, nonylphenol, cardanols and their derivatives such as cardols, methylcardols and anacardial acids contained in particular in the cashew nut shell liquid (CNSL) and naphthol, and the precursors of these alcohols, in particular the acetals and trioxanes.
  • CNSL cashew nut shell liquid
  • reactive diluents comprising aldehyde functions
  • reactive diluents comprising epoxy functional groups
  • glycidyl ethers of saturated or unsaturated alcohols such as the diglycidyl ether of hexane-1,6-diol, the epoxidized fatty acids in particular contained in epoxidized oils.
  • soybean oil Ecocet ®; Arkema
  • linseed oil Vikoflex ®, Arkema
  • aromatic epoxy such as epoxidized cardanols, including 3-n-pentadécadiénylphénol.
  • reactive diluents comprising oxazolidine functional groups
  • the preferred lactone functional reactive diluent is gamma-butyrolactone.
  • the gamma butyrolactone mixed with triphenylphosphite which makes it possible to improve the thermal resistance of the liquid resin composition,
  • Preferred diluents are glycerol, furfuryl alcohol, benzyl alcohol, cardols and their derivatives (CNSL), diglycidyl ether of hexane-1,6-diol, epoxidized cardanols, 3-ethyl-2- methyl- (3méthylbutyl) -
  • the reactive diluent represents at least 10% by weight of the resin composition, preferably at least 20%, and preferably does not exceed 69%, preferably 30%. Below 10%, the viscosity of the resin composition is too great for it to be used in the targeted applications. Above 69%, the mechanical properties of the final abrasive product are not satisfactory.
  • the crosslinking agent must have a high reactivity with respect to the novolac resin and the reactive diluent.
  • the crosslinking agent is chosen from compounds containing at least one hydroxyl or aldehyde function, the heterocyclic compounds containing a structure containing a nitrogen atom and an oxygen atom separated by a carbon atom, nitroacetals and nitrones.
  • compounds containing at least one hydroxyl function mention may be made of nitroalcohols such as ths (hydroxymethyl) nitromethane.
  • oxazolines such as 1,3-phenylenebisoxazoline
  • oxazolidines such as 3 ethyl-2-methyl-2- (3-methylbutyl) -1,3-oxazolidine and 1-aza-3,7-dioxa-5-ethylbicyclo (3.3.0) octane.
  • the preferred crosslinking agent is tris (hydroxymethyl) nitromethane, glyoxal, 3-ethyl-2-methyl-2- (3-methylbutyl) -1,3-oxazolidine and 1-aza-3,7-dioxa. -5-éthylbicyclo- (3.3.0) octane. 1 -aza-3,7-dioxa-5-ethylbicyclo [3.3.0] octane is particularly advantageous because it can act as both a reactive diluent and a crosslinking agent.
  • the crosslinking agent preferably represents at least 1% by weight of the liquid resin composition, advantageously at least 20%, and more preferably at least 30%, and generally does not exceed 40%.
  • the liquid resin composition may further comprise at least one crosslinking catalyst.
  • the catalyst is chosen from compounds comprising at least one secondary or tertiary amine function such as hydroxylamine, triethylamine, diazabicycloundecene, benzyldimethylamine and 2,4,6-tri (dimethylaminomethyl) phenol, imidazoles and imidazole derivatives, for example 2-methyl-imidazole, 2-ethyl-4-methyl-imidazole and 1-benzyl-2-methyl-imidazole, trialkyl- and triaryl-nucleophiles of Group V elements ( A) for example triethanolamine, trimethylphosphine and triphenylphosphine, borates, for example tetraphenylphosphonium tetraphenylborate and tetraphenylphosphonium tetrafluoroborate, and ammonium salts such as tetramethylammonium hydroxide and benzyltrimethylam
  • Catalysts in liquid form are preferred, essentially for reasons of ease of implementation.
  • the amount of catalyst in the liquid resin composition is less than or equal to 10 parts by weight per 100 parts by weight of novolak resin, of reactive diluent and optionally of crosslinking agent, and preferably is less than or equal to 5 parts .
  • the preparation of the liquid resin composition can be done by simply mixing the constituents in a suitable container, advantageously provided with stirring means; preferably, the novolac resin is introduced into the reactive diluent, then the crosslinking agent and the catalyst are optionally added.
  • the mixture of the constituents may be at room temperature, of the order of 20 to 25 ° C, or at a higher temperature, preferably at least 10 ° C. higher than the glass transition temperature of the novolac resin. and advantageously less than or equal to 50 ° C. so as to prevent the crosslinking and / or the thermal degradation of the constituents of the resin composition.
  • the viscosity of the liquid resin composition depends on the intended application but remains less than or equal to 7000 mPa.s.
  • the liquid resin composition according to the invention is used to manufacture agglomerated abrasives.
  • the liquid resin composition is first mixed with abrasive grains in a conventional mechanical mixer until the grains are suitably "wetted", i.e., coated with the resinous composition, and then the binder powder and the additives, also in powder form, until a homogeneous granular mixture is obtained.
  • the liquid resin composition has a viscosity at most equal to 3000 mPa.s, and advantageously greater than or equal to 600 mPa.s.
  • the starting temperature of crosslinking of the resin in the granular mixture is at most equal to 245 ° C., and advantageously at most equal to 195 ° C.
  • the time required to obtain complete crosslinking of the resin composition in the granular mixture is less than or equal to 36 hours, preferably less than or equal to 20 hours.
  • the abrasive grains may be any type of known abrasive grains, for example composed of alumina, including fused aluminas and sintered aluminas obtained by sol-gel, seeded or not with a material of the same crystalline nature, chemically modified or not, iron oxide, molybdenum oxide, vanadium oxide, alumina-zirconia, boron-alumina, silicon carbide, aluminum-oxynitride, diamond or cubic boron nitride, and mixtures of such grains.
  • the abrasive grains are alumina.
  • the abrasive grains are pretreated with an organic compound which improves the adhesion between the grain and the liquid resin composition, chosen from compounds containing silicon, for example a silane functionalized with organic groups such as vinylsilane, especially vinyltriethoxysilane, an aminosilane, especially gamma-aminopropyltrimethoxysilane, gamma-aminopropyltriethoxysilane and diaminopropylethoxysilane, or an epoxysilane.
  • gamma-aminopropyltriethoxysilane is used.
  • the treatment of the abrasive grains with the organic compound containing silicon can be carried out for example by spraying a solution of said compound in a suitable solvent, most often water, or by dispersing the grains in the aforementioned solution.
  • the treated abrasive grains are dried before being mixed with the liquid resin composition.
  • a liquid organic carrier can be added to the abrasive grain mixture and the resinous composition, which aids in grain wetting and the formation of a uniform grain network, and which is subsequently removed in the course of time. crosslinking step.
  • the organic carrier may be water, an aliphatic alcohol, a glycol, high molecular weight oil fractions of oily or waxy consistency, mineral oil or any other known vehicle.
  • the binder may be a phenol-aldehyde, melamine-aldehyde, urea-aldehyde, polyester, polyimide, epoxy, polyurethane or polybenzimidazole resin.
  • the binder is a low formaldehyde resin, advantageously a novolak type phenol-aldehyde resin, and more preferably a phenol-formaldehyde novolac resin.
  • the additives are, for example, fillers, crosslinking agents and other compounds which are useful for the manufacture of agglomerated abrasives, in particular bound by an organic resin.
  • the fillers are generally in the form of a finely divided powder comprising particles that may have the appearance of granules, spheres or fibers.
  • sand silicon carbide
  • alumina hollow spheres bauxite
  • chromites magnesite
  • dolomites hollow mullite spheres
  • borides silica fume, titanium dioxide, carbon products (carbon black, coke, graphite, ...), wood flour, clay, talc, hexagonal boron nitride, molybdenum disulfide, feldspar, nepheline syenite and glass, especially in the form of solid, hollow or hollow beads, and fibers.
  • the fillers represent 0.1 to 30% by weight of the granular mixture.
  • Crosslinking agents are used when the powder binder is a novolac resin. They may be chosen from compounds known to perform the aforementioned function such as hexamethylenetetramine or precursors of it.
  • the crosslinking agent is added in an amount of 5 to 20 parts by weight per 100 parts by weight of novolac resin powder.
  • the additives may further comprise agents which assist in the implementation of the process, for example anti-static agents and lubricants.
  • agents which assist in the implementation of the process for example anti-static agents and lubricants.
  • the amount of these additives can be easily determined by those skilled in the art.
  • the granular mixture is subjected to a ripening treatment at room temperature for a period of about 12 hours.
  • the granular mixture is then introduced into a mold equipped with compression means for forming a green part which has sufficient cohesion to be handled and processed in the following steps without substantially changing its shape.
  • the binder at this stage is in the uncrosslinked state.
  • the green part is then heated to a temperature sufficient for the binder to crosslink and give a rigid polymeric network which gives the piece its final shape.
  • the crosslinking is carried out according to a conventional baking cycle which consists of bringing the green part to a temperature of the order of 100 ° C. and keeping it at this temperature for 30 minutes to several hours so that the volatile products formed can be removed. .
  • the room is heated to the final temperature over a period that generally ranges from 10 to 36 hours.
  • the final crosslinking temperature depends in particular on the nature of the resin used, the size and shape of the piece to be treated and the cooking time. In general, the final crosslinking temperature is between 100 and 200 ° C.
  • the thermal crosslinking is carried out in a controlled atmosphere, preferably with a maximum relative humidity level.
  • the agglomerated abrasives obtained may be in the form of grinding wheels, segments of grinding wheels, discs and whetstones.
  • the liquid resin composition according to the invention is used to produce coated abrasives.
  • the manufacture of the coated abrasives comprises the steps of depositing a base coat ("make coat") on a support material, to distribute the grains of abrasives on said layer, subjecting said material to a heat treatment for partially cross-linking the resin composition, depositing a top adhesive layer ("size coat”) and subjecting the heat treated coated material to in order to obtain complete crosslinking of the resin composition. If necessary, an additional adhesive layer may be deposited on the upper adhesive layer and crosslinked by a suitable heat treatment.
  • the support material generally has a moderate to strong flexibility, and has the appearance of a sheet, in particular paper, a film, in particular polymer, or a more or less dense network of natural or synthetic fibers, for example. Examples of glass fibers and vulcanized fibers.
  • the abrasive grains may be chosen from the grains already mentioned which form part of the agglomerated abrasives.
  • the application of the grains on the base adhesive layer can be done by the usual techniques operating by gravity or electrostatically.
  • the density of the abrasive grains on the support is to be chosen according to the intended application.
  • the liquid resin composition according to the invention may be used to form the base adhesive layer ("make coat"), the upper adhesive layer ("size coat”) or the additional adhesive layer “supersize coat”).
  • the liquid resin composition serves to form the base adhesive layer and the upper adhesive layer, and optionally the additional adhesive layer.
  • the liquid resin composition has a viscosity of less than or equal to 6000 mPa.s and a start of crosslinking temperature at most equal to 150 0 C, preferably at most equal to 120 0 C.
  • the liquid resin composition contains at least one aforementioned crosslinking agent.
  • the time necessary to obtain complete crosslinking of the resin composition is less than 36 hours, preferably less than 20 hours.
  • the basic, superior and additional adhesive layers which are not formed from the liquid resin composition according to the invention may be chosen from phenolic resins, urea formaldehyde, epoxy, urethane, acrylic, aminoplast, melamine and mixtures of these resins.
  • the resin or resin mixture has the lowest possible free formaldehyde level.
  • the liquid resin composition may further comprise additives, for example wetting agents, fillers, coupling agents, dyes, pigments and antistatic agents.
  • the liquid resin composition When used to form the upper adhesive layer and / or the additional adhesive layer, it advantageously comprises at least one agent which enhances the abrasive performance of the final abrasive.
  • an agent can be chosen from waxes, halogenated organic compounds, halogen salts, metals and metal alloys.
  • the heat treatment of the support material coated with the liquid resin composition forming the base adhesive layer is carried out at a temperature of less than or equal to 150 ° C., preferably less than or equal to 120 ° C. for 1 to 120 minutes, preferably 1 to 60 ° C. minutes.
  • the conditions of the heat treatment for the crosslinking of the resin composition forming the upper adhesive layer or the additional adhesive layer may be at a temperature of less than or equal to 150 ° C., preferably less than or equal to 120 ° C. for at most 36 hours. preferably at most 20 hours.
  • the crosslinking start temperature is measured by Dynamic Mechanical Analysis (DMA): the liquid resin composition is introduced between two glass plates and the assembly is placed horizontally on a device comprising two fixed lower jaws remote from each other; 40 mm and an upper jaw applied against the upper sheet located 20 mm from each of the preceding jaws. On the upper jaw, a force of 8OmPa is applied with an oscillation frequency of 1 Hz and heating the whole 25 to 300 ° C at a rate of 4 ° C / minute. The elastic modulus of the resin composition is measured as a function of the temperature and from the established curve the starting temperature of the crosslinking is determined.
  • DMA Dynamic Mechanical Analysis
  • the loss of mass at 500 ° C. is determined by thermogravimetric analysis (DTA): the liquid resin composition is deposited in an aluminum cup and heated according to a given temperature cycle. 10 to 20 mg of the crosslinked resin composition are placed in an alumina crucible which is placed in an apparatus continuously measuring the loss of mass during a temperature cycle ranging from 25 ° to 700 ° C. at a rate of 10 ° C. C / minute. On the recorded curve, the loss of mass is determined at 500 ° C.
  • DTA thermogravimetric analysis
  • Liquid resin compositions having the composition given in Table 1 (in parts by weight) are prepared.
  • the resins are obtained by solubilizing the novolak resin in the reactive diluent at ambient temperature (20-25 ° C.) and with moderate stirring, and then adding the crosslinking agent and the catalyst while maintaining the stirring conditions.
  • compositions are then subjected to an annealing treatment at 200 ° C. for 2 hours, and then they are cooled to ambient temperature.
  • Granular mixtures having the composition given in the following Table 2 are prepared:
  • test pieces are obtained by molding 75.64 g of the granular mixture obtained under b) in a mold measuring 10.224 cm ⁇ 2.591 cm ⁇ 1.27 cm.
  • the green test pieces are removed from the mold, sealed in aluminum foil and cured in an oven according to the following temperature cycle:
  • test pieces are separated into two series: the first series undergoes no treatment, the second is immersed in boiling water for 2 hours to simulate the conditions of accelerated aging.
  • Liquid resin compositions for the manufacture of coated abrasives are prepared under the conditions of Examples 1 to 12.
  • Liquid resin compositions for the manufacture of coated abrasives are prepared under the conditions of Examples 1 to 12.
  • Liquid resin compositions for the manufacture of agglomerated abrasives are prepared:
  • the resins are obtained by solubilizing the novolac resin in the reactive diluent at a temperature of the order of 35 to 40 ° C.
  • liquid resin compositions are processed according to the temperature and annealing cycle described in paragraph a) of Examples 1 to 12 above.
  • Granular mixtures having the following composition are prepared:
  • the abrasive grains are grains of 60 grain alumina (406 ⁇ m) (9) which were previously immersed in an aqueous solution of gamma-aminopropyltriethoxysilane at 2% by weight, and then dried in an oven at 120 ° C. for 2 hours. .
  • test specimens are obtained by molding the granular mixture under the conditions of Examples 1 to 12.
  • test pieces are separated into two series: the first series undergoes no treatment, the second is immersed in boiling water for 2 hours to simulate the conditions of accelerated aging.
  • HEXA hexamethylenetetramine
  • TNE tris (hydroxymethyl) nitromethane
  • TEA triethanolamine
  • TNE tris (hydroxymethyl) nitromethane
  • TEA triethanolamine
  • TPP triphenylphosphine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Mechanical Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Composite Materials (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polishing Bodies And Polishing Tools (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP08842341A 2007-10-01 2008-10-01 Composition resinique liquide pour articles abrasifs Withdrawn EP2195383A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0706881A FR2921666B1 (fr) 2007-10-01 2007-10-01 Composition resinique liquide pour articles abrasifs
PCT/FR2008/051778 WO2009053580A2 (fr) 2007-10-01 2008-10-01 Composition resinique liquide pour articles abrasifs

Publications (1)

Publication Number Publication Date
EP2195383A2 true EP2195383A2 (fr) 2010-06-16

Family

ID=39111577

Family Applications (1)

Application Number Title Priority Date Filing Date
EP08842341A Withdrawn EP2195383A2 (fr) 2007-10-01 2008-10-01 Composition resinique liquide pour articles abrasifs

Country Status (8)

Country Link
US (1) US8523967B2 (zh)
EP (1) EP2195383A2 (zh)
CN (1) CN101883824B (zh)
AR (1) AR068643A1 (zh)
CL (1) CL2008002931A1 (zh)
FR (1) FR2921666B1 (zh)
TW (1) TWI523909B (zh)
WO (1) WO2009053580A2 (zh)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2959226B1 (fr) * 2010-04-21 2012-05-25 Saint Gobain Technical Fabrics Structure de fils de verre destinee a renforcer des articles abrasifs agglomeres.
AU2012251025B2 (en) * 2011-05-05 2016-05-12 Basf Se Resin-coated proppant and methods of use
MY153895A (en) * 2012-06-01 2015-04-08 Tkx Corp Adhesive composition for resin-bonded wire saw and method for producing resin-bonded wire saw
CN103409096B (zh) * 2013-08-16 2014-10-15 石家庄世易糠醛糠醇有限公司 一种环保无甲醛木材专用呋喃类树脂胶粘剂的制备方法
CN103421419B (zh) * 2013-08-16 2015-10-14 石家庄世易糠醛糠醇有限公司 一种高性能呋喃类海洋防腐涂料的制备方法
WO2015077918A1 (en) * 2013-11-26 2015-06-04 Dow Global Technologies Llc Curing agent composition
CN103911059B (zh) * 2014-04-28 2016-04-27 上海茂霖高分子科技股份有限公司 一种用于半导电胶辊的中阻值耐磨涂层及其制备方法
CN103911060B (zh) * 2014-04-28 2016-04-27 上海茂霖高分子科技股份有限公司 一种用于半导电胶辊的低阻值耐磨涂层及其制备方法
US11235436B2 (en) * 2016-07-08 2022-02-01 Saint-Gobain Abrasives, Inc. Abrasive articles and methods of forming the same
US20200332162A1 (en) * 2017-12-18 2020-10-22 3M Innovative Properties Company Phenolic resin composition comprising polymerized ionic groups, abrasive articles and methods
CN109628033A (zh) * 2018-12-29 2019-04-16 广西六万山林业有限公司 一种环保型胶合板用胶粘剂及其制备方法与应用
CN110483716B (zh) * 2019-08-20 2021-04-27 吉林大学 一种原位自增强聚亚胺复合材料及其制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001214028A (ja) * 2000-02-02 2001-08-07 Ube Ind Ltd 耐熱性液状フェノールノボラック樹脂及びその硬化物
WO2005108454A1 (en) * 2004-04-23 2005-11-17 Angus Chemical Company Phenolic resin

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB985751A (en) * 1960-03-29 1965-03-10 Norton Co Improvements in or relating to abrasive products
US4487868A (en) * 1983-05-25 1984-12-11 Acme Resin Corporation Foundry core compositions
DE3705540A1 (de) * 1986-06-13 1987-12-17 Ruetgerswerke Ag Hochtemperaturbestaendige formstoffe
US5014468A (en) * 1989-05-05 1991-05-14 Norton Company Patterned coated abrasive for fine surface finishing
DE3915823A1 (de) * 1989-05-16 1990-11-22 Ruetgerswerke Ag Verfahren zur herstellung von verbundwerkstoffen
US5441549A (en) * 1993-04-19 1995-08-15 Minnesota Mining And Manufacturing Company Abrasive articles comprising a grinding aid dispersed in a polymeric blend binder
DE4423913A1 (de) * 1994-07-07 1996-01-11 Ruetgerswerke Ag Flüssige Bindemittel
TW383322B (en) 1994-11-02 2000-03-01 Norton Co An improved method for preparing mixtures for abrasive articles
US5686506A (en) * 1995-04-04 1997-11-11 Borden Chemical, Inc. Mixtures of phenolic novolaks for use with refractory aggregate and methods for making same
BR9612464A (pt) * 1995-12-27 1999-07-13 Borden Chem Inc Diluentes reativos para composições fenólicas curáveis por ácidos
CA2263418A1 (en) * 1996-09-20 1998-03-26 James Edward Hoge Resin transfer molding process using stable epoxy resin compositions
US5908881A (en) * 1996-11-29 1999-06-01 Sumitomo Bakelite Company Limited Heat-conductive paste
US5910521A (en) 1998-04-01 1999-06-08 Borden Chemical, Inc. Benzoxazine polymer composition
US6514302B2 (en) * 2001-05-15 2003-02-04 Saint-Gobain Abrasives, Inc. Methods for producing granular molding materials for abrasive articles
US6949129B2 (en) * 2002-01-30 2005-09-27 Saint-Gobain Abrasives, Inc. Method for making resin bonded abrasive tools
FR2921667B1 (fr) 2007-10-01 2012-11-09 Saint Gobain Abrasives Inc Composition resinique liquide pour articles abrasifs

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001214028A (ja) * 2000-02-02 2001-08-07 Ube Ind Ltd 耐熱性液状フェノールノボラック樹脂及びその硬化物
WO2005108454A1 (en) * 2004-04-23 2005-11-17 Angus Chemical Company Phenolic resin

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"ASTM D3418-08 Standard Test Method for Transition Temperatures and Enthalpies of Fusion and Crystallization of Polymers by Differential Scanning Calorimetry", 1 January 2008, ASTM INTERNATIONAL, article "ASTM D3418-08 Standard Test Method for Transition Temperatures and Enthalpies of Fusion and Crystallization of Polymers by Differential Scanning Calorimetry", XP055070965 *

Also Published As

Publication number Publication date
AR068643A1 (es) 2009-11-25
CN101883824A (zh) 2010-11-10
FR2921666A1 (fr) 2009-04-03
CN101883824B (zh) 2014-08-06
FR2921666B1 (fr) 2012-11-09
TW200932823A (en) 2009-08-01
WO2009053580A3 (fr) 2009-06-25
CL2008002931A1 (es) 2009-09-04
US8523967B2 (en) 2013-09-03
WO2009053580A2 (fr) 2009-04-30
US20100298505A1 (en) 2010-11-25
TWI523909B (zh) 2016-03-01

Similar Documents

Publication Publication Date Title
EP2195383A2 (fr) Composition resinique liquide pour articles abrasifs
WO2009053581A1 (fr) Composition resinique liquide pour articles abrasifs
KR101211944B1 (ko) 페놀수지 제형 및 연마제품용 코팅재
BE1015339A5 (fr) Procede de production d'outils abrasifs lies a la resine.
US8012574B2 (en) Carbon fiber Ti-Ai composite material and method for preparation thereof
JP2003292943A (ja) 湿式摩擦材用樹脂組成物および湿式摩擦材
JP2018188323A (ja) 炭素短繊維強化複合材料およびその製造方法
JP2004268195A (ja) レジノイド砥石及びその製造方法
JP5376238B2 (ja) フェノール樹脂の製造方法
FR2771151A1 (fr) Composition de garniture de friction contenant une resine phenolique
WO2009141568A2 (fr) Article abrasif sans formaldehyde
CN114571377B (zh) 一种pai树脂基砂轮及其制备方法
JP3543866B2 (ja) 摩擦材及びその製造方法
JP5977531B2 (ja) 摩擦調整材の製造方法
JP2004156045A (ja) 摩擦材
JP7131713B2 (ja) 摩擦材用フェノール樹脂組成物
JP3583872B2 (ja) 炭素・樹脂複合材
JP2003292645A (ja) プリプレグ、および砥石
JP2013169636A (ja) レジノイド砥石及びこれに用いるフェノール樹脂組成物
BE369551A (zh)

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20100503

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA MK RS

17Q First examination report despatched

Effective date: 20101217

DAX Request for extension of the european patent (deleted)
GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

INTG Intention to grant announced

Effective date: 20180403

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20180814