EP0595003B1 - Composition thermodurcissable - Google Patents

Composition thermodurcissable Download PDF

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Publication number
EP0595003B1
EP0595003B1 EP93114722A EP93114722A EP0595003B1 EP 0595003 B1 EP0595003 B1 EP 0595003B1 EP 93114722 A EP93114722 A EP 93114722A EP 93114722 A EP93114722 A EP 93114722A EP 0595003 B1 EP0595003 B1 EP 0595003B1
Authority
EP
European Patent Office
Prior art keywords
oil
accordance
component
thermosetting mixture
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP93114722A
Other languages
German (de)
English (en)
Other versions
EP0595003A1 (fr
Inventor
Michael König
Achim Dr. Hansen
Arno Dr. Gardziella
Josef Suren
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.)
Hexion Specialty Chemicals AG
Original Assignee
Ruetgerswerke AG
Bakelite AG
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 Ruetgerswerke AG, Bakelite AG filed Critical Ruetgerswerke AG
Publication of EP0595003A1 publication Critical patent/EP0595003A1/fr
Application granted granted Critical
Publication of EP0595003B1 publication Critical patent/EP0595003B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • B24D3/20—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 and being essentially organic
    • B24D3/28—Resins or natural or synthetic macromolecular compounds
    • 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

Definitions

  • the invention relates to a new thermosetting mixture for the production of filler-containing molded articles or resin-bonded abrasive articles.
  • Free-flowing phenolic resins are usually used for this purpose, which form a good bond with the filler with the addition of various auxiliaries.
  • the abrasive grain is first coated with a liquid phenolic resin and then the powder resin is mixed, optionally with the addition of other abrasive substances or fillers, so that a free-flowing mixture is formed.
  • Resoles can be modified by adding other substances. These substances are also used alone as wetting agents.
  • US-A-1 537 454 discloses the production of grinding wheels, furfurol as a solvent, a plasticizer and a hardener being added to the phenolic resin. If necessary, a few drops of cresol oil, phenol or cresol can also be added.
  • the disadvantage of adding furfural is, however, that it not only envelops the abrasive grains as desired, but also sticks the dry resin particles together. Therefore, neutral anthracene oil is used in US-A-1 893 117; namely, the abrasive grain is first mixed with the powder resin and the anthracene oil and then mixed with furfural.
  • US-A-28 14 554 is concerned with the usual use of furfural in the manufacture of grinding wheels, anthracene oil being additionally used as an anti-dust agent after the mixture of abrasive grain and resin bond has been completely processed.
  • a liquid rubber-like copolymer is mixed with furfural so that it is possible to wet the abrasive grain and the phenolic resin in the mixture, the cresol or creosote or guaiacol in the mixer as a "receiving agent" for the resin particles, which have not deposited on the abrasive grain particles wetted with furfural in the liquid rubber. Thereafter, this liquid "absorbent" is to prevent the phenomenon known as "balling".
  • Creosote oil is known from the literature as a common anti-dusting agent, however, in order to achieve sufficient effectiveness, more oil must be introduced than is desirable in view of the grinding properties. In addition, it is relatively expensive and therefore also reduces the cost-effectiveness of the product.
  • hydrocarbon oils with a viscosity of 10 to 2000 mPas is also known as a wetting agent.
  • Suitable oils for this purpose are those which have only a slight dissolving effect on the phenolic resin at temperatures ⁇ 45 ° C.
  • These can be monohydric aliphatic alcohols with 6 to 18 carbon atoms or a phenol substituted with C6 to C18 alkyl groups or mixtures thereof, with the prerequisite that a wetting agent is liquid at room temperature.
  • the wetting agent can be mixed with the phenolic resin beforehand or added directly when all components are mixed.
  • the object of the invention is therefore to provide inexpensive, free-flowing, much more storage-stable, thermosetting mixtures which do not dust during their production, at the same time have good formability and an improved bond between the added abrasive grain or fillers, so that they can be used according to their Processing to abrasive or shaped bodies have high quality properties.
  • thermosetting mixture according to claim 1 and its special composition according to claims 2 to 9, and their use for the production of moldings and resin-bonded grinding wheels, according to claims 10 and 11.
  • thermosetting mixtures for the production of resin-bonded abrasive articles or moldings can be obtained if, on the one hand, a powder resin, namely a phenolic novolak, together with a hardener with a small amount of an oil-like substance that is liquid at room temperature form one component a. is mixed, and then this free-flowing, non-dusting powder with component b., consisting of the fillers or the abrasive grain and other additives which have been intensively mixed beforehand with a liquid resol, is processed so that a homogeneous, non-sticky , powdery mixture. It is also possible to use other grain wetting agents, e.g. Creosote oil, furfuryl alcohol, etc., and the use of its dry mixes.
  • a powder resin namely a phenolic novolak
  • component b. consisting of the fillers or the abrasive grain and other additives which have been intensively mixed beforehand with a liquid resol
  • thermosetting mixture produced using the powder resin according to the invention requires practically no maturing times, since they are distinguished by very constant properties.
  • the powder resin to which the hardener, in particular hexamethylenetetramine, has been mixed beforehand, can be mixed with the oil-like substance.
  • the hardener in particular hexamethylenetetramine
  • a thermosetting mixture is obtained at the end, which is free-flowing even after a long storage or transport time, can be shaped well and, after processing, leads to grinding wheels with improved grinding performance and durability.
  • substances that are liquid at room temperature and have hydrophobic but non-adhesive properties can be used as the oil-like substance, but they do not interfere with the curing reaction, but act as a hydrophobic release agent under normal pressure and at room temperature.
  • These can be both mineral and animal oils, but also other hydrophobizing substances with polar substituents.
  • Long-chain, neutral hydrocarbons such as. B. paraffin. Chlorinated paraffin can also be used.
  • aliphatic monoalcohols alkanols
  • 6 to 18 carbon atoms in the carbon chain are also suitable. It can be primary, secondary or tertiary alcohols. Straight chain or little branched aliphatic chains are preferred. Further branches are less desirable because they lead to higher volatility for a given molecular weight and may also have a higher dissolving power on the heart. Chain lengths below 6 C atoms are not sufficient due to the volatility of the substances and chain lengths above 18 C atoms lead to solid alcohols.
  • the wetting agent must be liquid. Mixtures of high molecular weight and low molecular weight alcohols meet this requirement.
  • alcohols which can be used according to the invention are hexyl, n-heptyl, lauryl, n-octyl, capryl, n-nonyl, n-decyl, myristyl, cetyl or stearyl alcohol. 2-Ethylhexanol, decanol, dodecanol, tridecanol, octadecanol and mixtures thereof are preferred. Mixtures are necessary when an alcohol is solid. This is generally the case if the carbon chain contains more than 12 carbon atoms.
  • Phenols substituted with aliphatic hydrocarbon groups can also be used. A chain length of 6 to 18 carbon atoms can be used. These substituents are preferably in the p-position. No other substituents on the phenol other than the alkyl groups are contemplated by the invention. Examples of phenols are p-n-decyl, p-n-dodecyl, n-octadecylphenol and other alkyl substituents, as are given in the context of the description of the aliphatic alcohols.
  • a liquid product of vegetable type or of petroleum with a viscosity in the range between 100 and 2000 mPas is suitable as the hydrocarbon oil.
  • petroleum-based oils can have this viscosity range.
  • Mineral oils, aromatic concentrates, naphthenic oils, diesel oil, terpenes and limonene are suitable oils, provided that the commercial products available have the appropriate viscosity and no solvent effect.
  • Castor oil or cashew nut oil for example, can be used as natural oils.
  • Mixtures of alcohol and oil are useful and desirable, especially when the alcohol is a solid.
  • the novolak-hardener mixture can be rendered hydrophobic if the mixing takes place at elevated temperatures. It is also possible, however, to apply the oily substance melted at low temperature to the resin-hardener mixture by spraying, with simultaneous intensive mixing.
  • Mono- or polynuclear phenols or mixtures of the class of compounds mentioned can be used as phenolic components, both mono- and polynuclear phenols.
  • phenol itself, and its alkyl-substituted homologs, such as o-, m- or p-cresol, xylenes or higher alkylated phenols, and also halogen-substituted phenols, such as chloro- or bromophenol and polyhydric phenols such as resorcinol or pyrocatechol, and polynuclear Phenols such as naphthols, bisphenol A or bisphenol F.
  • alkyl-substituted homologs such as o-, m- or p-cresol, xylenes or higher alkylated phenols
  • halogen-substituted phenols such as chloro- or bromophenol and polyhydric phenols such as resorcinol or pyrocatechol
  • polynuclear Phenols such as naphthols, bisphenol A or bisphenol F.
  • the phenol or the phenolic component is reacted with formaldehyde or a compound which releases formaldehyde to give the desired novolak.
  • the novolaks can be modified by conventional modifiers, e.g. Epoxy resins, rubbers, polyvinyl butyral and inorganic additives can be modified.
  • resoles which are obtained by alkaline condensation of a phenol with formaldehyde or a compound which releases formaldehyde are suitable for wetting the fillers or the abrasive grain with a liquid resole.
  • Resoles obtained by the reaction of a phenol and formaldehyde in a molar ratio of 1: 0.7 to 1: 4 are particularly suitable.
  • Condensation products with a molar ratio of 1: 1 are preferably used.
  • Resoles which have a monomer content of 0-35% can be used; those with a content of 5 to 20% are preferred. Furthermore, these resols can be modified in the usual way.
  • phenols listed above can be used as the phenolic component for the production of corresponding resoles.
  • Fillers or abrasive grains such as aluminum oxide, SiC, FeS2, Na3 [AlF3] and / or potassium fluoroborate, finely divided copolymer of vinylidene chloride and vinyl chloride, potassium sulfate, zinc sulfate and barium sulfate can be mixed with the resole.
  • component a is done by 3 to 16 wt .-% hexamethylenetetramine with 79 to 96.5 wt .-% of a novolak are mixed intensively and then mixed with 0.5 to 5% by weight of an oil or an oil-like substance.
  • Mixing can be done by grinding together, by stirring or in a suitable commercially available mixer. If oil-like substances are used that only melt at temperatures slightly above the mixing temperature, it is possible to melt them beforehand and spray them on in a suitable mixer.
  • component b. is carried out by mixing 1.5 to 8% by weight, preferably about 5% by weight, with the abrasive grain or fillers in such a way that the individual grain or particles as a whole are coated with a thin resole film.
  • additives such as silanes, furfurylaldelyd etc. can also be added in generally customary amounts.
  • the actual storable thermoset mixture, from which grinding and shaped articles with improved properties can be produced in a known manner by pressing and curing, is obtained by 7 to 14% by weight of component a.,
  • the so-called powder resin, with 86 to 93 % By weight of component b. be intimately mixed.
  • the resins are ground in such a way that the following finenesses are achieved: TABLE 2 A 8 to 14% by weight > 45 ⁇ B 22 to 28% by weight > 45 ⁇ C. 0.5 to 1% by weight > 45 ⁇
  • the resins of Examples 1 to 8 / A to C are each homogeneously mixed with 1% by weight, 1.5% by weight, 2% by weight and 4% by weight of paraffin oil. These mixtures are designated D in the following.
  • hexamethylene tetramine is first ground alone to a fineness of 0.5 to 1.0% by weight> 45 ⁇ and mixed with 15% by weight paraffin oil, based on the amount of hexamethylene tetramine, and then with the resin mixed.
  • M-mixtures Grinding wheel mixtures for metalworking (M-mixtures) are produced by mixing a liquid resol with the abrasive grain and then mixing in the powder resin and the fillers. The following quantities are mixed with one another to produce such mixtures: Liquid resol * 12 kg Grain (Al2O3) NK 24 52 kg Grain (Al2O3) NK 36 128 kg Pyrox 16 kg Cryolite 8 kg Powder resin 27 kg * Bakelite SW 433
  • grinding wheel mixtures for stone processing are produced by mixing the following quantities: Liquid resol * 5 kg Grain (SiC) NK 24 25 kg Grain (SiC) NK 36 50 kg Grain (SiC) NK 46 25 kg Cryolite 12 kg Powder resin 10 kg * Bakelite SW 433

Landscapes

  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Polishing Bodies And Polishing Tools (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Laminated Bodies (AREA)

Claims (11)

  1. Composition thermodurcissable consistant en novolaque, résol et matières de charge, ainsi cu'éventuellement en des additifs, caractérisée en ce qu'elle est préparée à partir des composants
    a. constitués par une novolaque solide, un durcisseur et une huile ou une substance huileuse oui, à des températures au-dessous de 50°C, n'exerce d'effet dissolvant ni sur la résine en poudre, ni sur le durcisseur, et
    b. par un mélange composé d'un résol, de matières de charge, respectivt. de grains abrasifs et éventuellement d'additifs.
  2. Composition thermodurcissable selon la revendication 1, caractérisée en ce que le composant a. contient de l'hexaméthylènetétramine en tant que durcisseur.
  3. Composition thermodurcissable selon la revendication 1, caractérisée en ce que le composant a. est préparé par mélange homogène d'un mélange de novolaque-durcisseur avec une huile ou une substance huileuse.
  4. Composition thermodurcissable selon la revendication 1, caractérisée en ce que le composant a. est préparé par mélange intime du durcisseur avec une huile ou une substance huileuse et incorporation subséquente de la novolaque.
  5. Composition thermodurcissable selon la revendication 2, caractérisée en ce que le composant a. contient 3 à 16% en poids d'hexaméthylènetétramine, 79 à 96,5% en poids de novolaque, ainsi que 0,5 à 5% en poids d'une huile ou d'une substance huileuse.
  6. Composition thermodurcissable selon la revendication 1, caractérisée en ce que le composant a. contient de l'huile de paraffine en tant qu'huile.
  7. Composition thermodurcissable selon la revendication 1, caractérisée en ce que le composant a. contient une huile ou une substance huileuse du groupe de l'huile d'anthracène, de l'huile naphténique, du diesel-oil, du terpène, du limonène, de la paraffine chlorée et/ou un composé hydroxylé, tel que les alcools n-hexylique, n-heptylique, laurique, n-octylique, caprylique, n-nonylique, n-décylique, myristylique, cétylique, stéarylique, le 2-éthylhexanol, le décanol, le dodécanol, le tridécanol, l'octadécanol, le p-n-décylphénol, le p-n-dodécylphénol, le n-octadécylphénol, le nonylphénol.
  8. Composition thermodurcissable selon la revendication 1, caractérisée en ce que le composant b. contient un résol liquide préparé par condensation basique de phénol et de formaldéhyde dans le rapport molaire de 1:0,7 à 1,4, en particulier dans le rapport de 1:1, ainsi que de l'oxyde d'aluminium, SiC, FeS₂, Na₃[AlF₃] et/ou des fluoborates de potassium, un copolymère de chlorure de vinylidène et de chlorure de vinyle finement divisé, du sulfate de potassium, du sulfate de zinc et du sulfate de baryum en tant qu'abrasif et matière de charge.
  9. Composition thermodurcissable selon la revendication 1, caractérisée en ce que le composant b. contient 3,5 à 7% en poids de résol liquide.
  10. Utilisation d'une composition thermodurcissable selon les revendications 1 à 9 pour la fabrication de corps moulés.
  11. Utilisation d'une composition thermodurcissable selon les revendications 1 à 9 pour la fabrication de corps abrasifs agglomérés par des résines.
EP93114722A 1992-10-28 1993-09-14 Composition thermodurcissable Expired - Lifetime EP0595003B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4236284 1992-10-28
DE4236284 1992-10-28

Publications (2)

Publication Number Publication Date
EP0595003A1 EP0595003A1 (fr) 1994-05-04
EP0595003B1 true EP0595003B1 (fr) 1995-11-15

Family

ID=6471487

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93114722A Expired - Lifetime EP0595003B1 (fr) 1992-10-28 1993-09-14 Composition thermodurcissable

Country Status (9)

Country Link
US (1) US5399606A (fr)
EP (1) EP0595003B1 (fr)
AT (1) ATE130231T1 (fr)
DE (2) DE4328345A1 (fr)
DK (1) DK0595003T3 (fr)
ES (1) ES2079305B1 (fr)
FR (1) FR2697262B3 (fr)
GR (1) GR940300031T1 (fr)
IT (1) IT1261939B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW383322B (en) * 1994-11-02 2000-03-01 Norton Co An improved method for preparing mixtures for abrasive articles
US5658360A (en) * 1995-08-02 1997-08-19 Norton Company Compression molding of abrasive articles using water as a temporary binder
US5750597A (en) * 1996-06-20 1998-05-12 Plastics Engineering Company Thermosetting resin compositions
DE19951250A1 (de) 1999-10-25 2001-05-03 Treibacher Schleifmittel Gmbh Schleifkorn mit schleifaktiver Ummantelung
US6514302B2 (en) * 2001-05-15 2003-02-04 Saint-Gobain Abrasives, Inc. Methods for producing granular molding materials for abrasive articles
US20090277098A1 (en) * 2004-12-06 2009-11-12 Klaus-Peter Spies Abrasive and Method of Fabricating Same
DE102005056368B4 (de) * 2004-12-06 2008-04-03 Klingspor Ag Schleifmittel und Verfahren zu dessen Herstellung
EP2177318B1 (fr) * 2009-04-30 2014-03-26 Saint-Gobain Abrasives, Inc. Article abrasif doté d'une rétention de grain et d'une performance améliorées

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH511678A (de) * 1969-02-12 1971-08-31 Minnesota Mining & Mfg Schleifkörper
US3888640A (en) * 1970-01-15 1975-06-10 Ver Schmirgel & Maschf Coating for flexible abrasive bands
PL74106B1 (fr) * 1971-05-26 1974-10-31
DE2657881A1 (de) * 1976-12-21 1978-06-22 Sia Schweizer Schmirgel & Schl Schleifmittel
JPS55131471A (en) * 1979-03-29 1980-10-13 Gunei Kagaku Kogyo Kk Producing resinoid grindstone
US4350498A (en) * 1980-12-24 1982-09-21 Norton Company Dampening agent for resin bonded grinding wheels
GB8812512D0 (en) * 1988-05-26 1988-06-29 Tba Industrial Products Ltd Phenolic moulding compositions
JPH02185373A (ja) * 1989-01-13 1990-07-19 Kanebo Ltd 合成砥石

Also Published As

Publication number Publication date
DE59300950D1 (de) 1995-12-21
ITRM930642A1 (it) 1995-03-24
ES2079305A2 (es) 1996-01-01
US5399606A (en) 1995-03-21
ITRM930642A0 (it) 1993-09-24
DE4328345A1 (de) 1994-05-05
EP0595003A1 (fr) 1994-05-04
ES2079305B1 (es) 1996-10-16
DK0595003T3 (da) 1995-12-18
GR940300031T1 (en) 1994-05-31
ES2079305R (fr) 1996-01-16
IT1261939B (it) 1996-06-04
ATE130231T1 (de) 1995-12-15
FR2697262B3 (fr) 1994-09-23
FR2697262A3 (fr) 1994-04-29

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