WO2011125614A1 - Composition durcissable pour composant résistant à la chaleur de dispositif de fabrication de semi-conducteurs, de cristaux liquides, de cellules solaires ou d'éléments électroluminescents (el) organiques - Google Patents

Composition durcissable pour composant résistant à la chaleur de dispositif de fabrication de semi-conducteurs, de cristaux liquides, de cellules solaires ou d'éléments électroluminescents (el) organiques Download PDF

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WO2011125614A1
WO2011125614A1 PCT/JP2011/057673 JP2011057673W WO2011125614A1 WO 2011125614 A1 WO2011125614 A1 WO 2011125614A1 JP 2011057673 W JP2011057673 W JP 2011057673W WO 2011125614 A1 WO2011125614 A1 WO 2011125614A1
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group
heat
curable composition
elastomer
mol
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PCT/JP2011/057673
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English (en)
Japanese (ja)
Inventor
恵子 鷲野
昌二 福岡
小西　智久
栄作 角野
剛 野口
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ダイキン工業株式会社
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Publication of WO2011125614A1 publication Critical patent/WO2011125614A1/fr

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    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
    • F16J—PISTONS; CYLINDERS; SEALINGS
    • F16J15/00—Sealings
    • F16J15/02—Sealings between relatively-stationary surfaces
    • F16J15/06—Sealings between relatively-stationary surfaces with solid packing compressed between sealing surfaces
    • F16J15/10—Sealings between relatively-stationary surfaces with solid packing compressed between sealing surfaces with non-metallic packing
    • F16J15/102—Sealings between relatively-stationary surfaces with solid packing compressed between sealing surfaces with non-metallic packing characterised by material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/28—Nitrogen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/43—Compounds containing sulfur bound to nitrogen

Definitions

  • the present invention relates to a heat-resistant component of a semiconductor, liquid crystal, solar battery, or organic electroluminescence (EL) manufacturing apparatus containing a vinylidene fluoride elastomer, particularly to a curable composition for a heat-resistant sealing material.
  • EL organic electroluminescence
  • TFE Tetrafluoroethylene
  • Patent Document 1 discloses tetrafluoroethylene, perfluoro (vinyl ether) using nitrogen-containing nucleophilic compounds such as aniline for perfluoroelastomers used in end uses in which exposure to high temperature and aggressive chemicals occurs. ), And perfluoroelastomer compositions comprising perfluoroelastomers having copolymerized units of nitrile-containing cure site monomers are disclosed.
  • Patent Documents 2 and 3 attempt to improve the heat resistance of vinylidene fluoride elastomers by requiring crosslinking using a specific curing agent. ing.
  • An object of the present invention is to provide a heat-resistant component composition and a heat-resistant component such as a sealing material used in a semiconductor, liquid crystal, solar cell, or organic EL manufacturing apparatus using a specific non-perfluoroelastomer.
  • the semiconductor manufacturing apparatus referred to in the present invention is not particularly limited to an apparatus for manufacturing a semiconductor, but is widely used in the semiconductor field where high heat resistance is required, such as an apparatus for manufacturing a liquid crystal panel or a plasma panel. Including general manufacturing equipment.
  • the present invention (A) Vinylidene fluoride (VdF) (a1) and at least one perfluoroolefin selected from the group consisting of tetrafluoroethylene (TFE), hexafluoropropylene (HFP) and perfluoro (alkyl vinyl ether) (PAVE) VdF elastomer (A1) which is a copolymer of (a2) and a monomer (a3) containing a cyano group, a carboxyl group or an alkoxycarbonyl group (however, the copolymerization ratio of VdF exceeds 20 mol%) Or a TFE-Pr elastomer (A2) which is a copolymer of 40 to 70 mol% of TFE, 30 to 60 mol% of propylene (Pr) and a monomer containing a cyano group, a carboxyl group or an alkoxycarbonyl group, And (B) a curing agent,
  • TFE t
  • the curing agent (B) has the formula (1): (Wherein R 1 is the same or different and is —NH 2 , —NHR 2 , —OH or —SH, and R 2 is a fluorine atom or a monovalent organic group) A compound comprising at least two compounds of formula (2): A compound of formula (3): (Wherein R f 1 is a perfluoroalkylene group having 1 to 10 carbon atoms), and formula (4): In the formula, at least one curing agent selected from the group consisting of compounds represented by the formula (n is an integer of 1 to 10) is preferred.
  • the ammonia generating compound (C) is preferably urea or an ammonium salt.
  • the present invention also relates to a heat-resistant component of a semiconductor, liquid crystal, solar cell, or organic EL manufacturing apparatus obtained by curing the curable composition of the present invention.
  • sealing material for semiconductor manufacturing equipment diffusion equipment As heat-resistant components, sealing material for semiconductor manufacturing equipment diffusion equipment, CVD equipment sealing material, PVD equipment sealing material, etching equipment sealing material or exhaust gas abatement equipment, or silicon manufacturing equipment sealing material, It is suitable as a sealing material for liquid crystal manufacturing apparatus, a sealing material for solar cell manufacturing apparatus, or a sealing material for organic EL manufacturing apparatus.
  • a heat-resistant component composition and a heat-resistant component such as a sealing material used in a semiconductor, a solar cell, a liquid crystal, or an organic EL manufacturing apparatus using a specific non-perfluoroelastomer.
  • non-perfluoroelastomer A1 or TFE-Pr elastomer (A2) (hereinafter sometimes referred to as “non-perfluoroelastomer (A)”) is a curing agent.
  • A1 a specific VdF elastomer
  • A2 TFE-Pr elastomer
  • B an ammonia generating compound
  • F inorganic nitride particles
  • the specific VdF-based elastomer (A1) includes VdF (a1), at least one perfluoroolefin (a2) selected from the group consisting of TFE, HFP and PAVE, a cyano group, It is a VdF elastomer which is a copolymer with a monomer (a3) containing a carboxyl group or an alkoxycarbonyl group.
  • CF 2 CFO (CF 2 CFY 2 O) p- (CF 2 CF 2 CF 2 O) q -R f 3 (7)
  • Y 2 represents a fluorine atom or —CF 3
  • R f 3 represents a perfluoroalkyl group having 1 to 5 carbon atoms
  • p represents an integer of 0 to 5
  • q represents 0 to Represents an integer of 5.
  • CFX CXOCF 2 OR (8) (Wherein X is F or H; R is a C 1 -C 6 linear or branched fluoroalkyl group, a C 5 -C 6 cyclic fluoroalkyl group, or a fluorooxyalkyl group, provided that (It may contain 1 to 2 atoms selected from H, Cl, Br, and I) Can be used alone or in combination of two or more.
  • perfluoro (methyl vinyl ether) and perfluoro (propyl vinyl ether) are preferable, and perfluoro (methyl vinyl ether) is particularly preferable.
  • the copolymerization ratio between VdF (a1) and the specific perfluoroolefin (a2) may be such that VdF exceeds 20 mol%, and in particular, VdF is 45 to 85 mol%, and specific perfluoroolefin 55 to 15 A VdF elastomer consisting of mol% is preferable, and a VdF elastomer consisting of 50 to 80 mol% of VdF and 50 to 20 mol% of a specific perfluoroolefin is more preferable.
  • VdF / HFP / monomer (a3) As a copolymer (A1) of VdF (a1), specific perfluoroolefin (a2) and monomer (a3), VdF / HFP / monomer (a3) copolymer, VdF / HFP / TFE / Monomer (a3) copolymer, VdF / PAVE / monomer (a3) copolymer, VdF / TFE / PAVE / monomer (a3) copolymer, VdF / HFP / PAVE / monomer (A3) A copolymer and VdF / HFP / TFE / PAVE / monomer (a3) copolymer are preferred.
  • the molar ratio of VdF / HFP is preferably 45 to 85/55 to 15 mol%, and more preferably 50 to 80/50 to 20 mol. %, And more preferably 60-80 / 40-20 mol%.
  • the VdF / HFP / TFE / monomer (a3) copolymer preferably has a VdF / HFP / TFE molar ratio of 40 to 80/10 to 35/10 to 35 mol%.
  • the VdF / PAVE / monomer (a3) copolymer preferably has a VdF / PAVE molar ratio of 65 to 90/35 to 10 mol%.
  • the VdF / TFE / PAVE / monomer (a3) copolymer preferably has a molar ratio of VdF / TFE / PAVE of 40 to 80/3 to 40/15 to 35 mol%.
  • the VdF / HFP / PAVE / monomer (a3) copolymer preferably has a molar ratio of VdF / HFP / PAVE of 65 to 90/3 to 25/3 to 25 mol%.
  • the VdF / HFP / TFE / PAVE / monomer (a3) copolymer is preferably a VdF / HFP / TFE / PAVE molar ratio of 40 to 90/0 to 25/0 to 40/3 to 35. 40 to 80/3 to 25/3 to 40/3 to 25 mol% is more preferable.
  • the monomer (a3) containing a cyano group, a carboxyl group or an alkoxycarbonyl group is selected from VdF (a1) and a specific perfluoroolefin (from the viewpoint of good crosslinking characteristics of the curable composition and heat resistance of the crosslinked product.
  • the content is preferably from 0.1 to 5 mol%, more preferably from 0.3 to 3 mol%, based on the total amount of a2).
  • VdF elastomers (A1) can be produced by a conventional method.
  • the presence of the functional group in the elastomer can be confirmed by, for example, infrared spectroscopic analysis.
  • the VdF elastomer (A1) used in the present invention preferably has a Mooney viscosity (ML 1 + 10 (121 ° C.)) of 5 to 140, more preferably 5 to 120, and particularly 5 to 100 from the viewpoint of good processability. .
  • TFE-Pr elastomer (A2) used in the present invention contains 40 to 70 mol% of TFE units, 30 to 60 mol% of Pr units, and a cyano group, a carboxyl group or an alkoxycarbonyl group.
  • VdF units and / or 0 to 15 mol% of PAVE units may be contained as necessary.
  • the TFE unit is 40 to 70 mol%, preferably 50 to 65 mol%, and Pr and elastomer properties are obtained in this range.
  • the Pr unit is 30 to 60 mol%, preferably 30 to 50 mol%, and elastomeric properties can be obtained in TFE and this range.
  • Examples of the monomer containing a cyano group, a carboxyl group or an alkoxycarbonyl group include the monomer (a3) described in the VdF elastomer (A1) and the TFE-Pr elastomer (A2). Can be used.
  • the VdF unit or PAVE unit which is an arbitrary unit, is up to 15 mol%, and further up to 10 mol%, and if it exceeds this, the former is not preferable in terms of amine resistance and the latter is expensive.
  • the TFE-Pr elastomer (A2) used in the present invention has a Mooney viscosity (ML 1 + 10 (121 ° C.)) of 5 to 100.
  • Mooney viscosity is less than 5, the vulcanizability is lowered and sufficient physical properties as a vulcanized rubber are not produced, and when it exceeds 100, the fluidity is lowered and the moldability tends to be deteriorated.
  • a preferable Mooney viscosity (ML 1 + 10 (121 ° C.)) is 10 to 80.
  • the TFE-Pr elastomer (A2) used in the present invention can be produced by a usual emulsion polymerization method. However, since the polymerization rate of TFE and Pr is relatively slow, for example, when produced by a two-stage polymerization method (seed polymerization method). Can be manufactured efficiently.
  • the curing agent (B) may be blended alone, or the ammonia generating compound (C) is blended alone.
  • the curing agent (B) and the ammonia generating compound (C) may be used in combination.
  • the inorganic nitride particles (F) may be blended alone for curing the VdF elastomer (A1) or the TFE-Pr elastomer (A2), or the curing agent (B) and Inorganic nitride particles (F) may be used in combination, ammonia generating compound (C) and inorganic nitride particles (F) may be used in combination, curing agent (B) and ammonia generating compound (C). ) And inorganic nitride particles (F) may be used in combination.
  • (B) Curing agent As the curing agent (B), the formula (1): (Wherein R 1 is the same or different and is —NH 2 , —NHR 2 , —OH or —SH, and R 2 is a fluorine atom or a monovalent organic group) A compound comprising at least two compounds of formula (2): A compound of formula (3): (Wherein R f 1 is a perfluoroalkylene group having 1 to 10 carbon atoms), and formula (4): In the formula, n is preferably at least one selected from the group consisting of compounds represented by the formula (1).
  • curing agents (B) 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane (OH-AF), which has excellent heat resistance and particularly good crosslinking reactivity, 2,2-bis [3-amino-4- (N-phenylamino) phenyl] hexafluoropropane (Nph-AF), 2,2-bis (3,4-diaminophenyl) hexafluoropropane (TA-AF) Is more preferable.
  • OH-AF 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane
  • TA-AF 2,2-bis (3,4-diaminophenyl) hexafluoropropane
  • These curing agents (B) may be used alone or in combination of two or more.
  • curing agents (B) react with a crosslinkable functional group such as a cyano group, a carboxyl group or an alkoxycarbonyl group of the specific non-perfluoroelastomer (A) used in the present invention to give a cross-linked product.
  • a crosslinkable functional group such as a cyano group, a carboxyl group or an alkoxycarbonyl group of the specific non-perfluoroelastomer (A) used in the present invention to give a cross-linked product.
  • the addition amount of the curing agent (B) is preferably 0.1 to 20 parts by mass, and 0.5 to 10 parts by mass with respect to 100 parts by mass of the specific non-perfluoro elastomer (A). Is more preferable.
  • the curing agent (B) is less than 0.1 parts by mass, there is a tendency that practically sufficient mechanical strength, heat resistance and chemical resistance cannot be obtained.
  • the crosslinked product tends to be hard and not flexible.
  • (C) Compound that generates ammonia at 40 to 330 ° C. (ammonia generating compound)
  • ammonia generating compound when at least one of the crosslinkable reactive groups of the specific non-perfluoroelastomer (A) is a cyano group, the cyano group forms a cyclized trimer (triazine ring). Triazine crosslinking system that promotes crosslinking reaction.
  • a curing agent is not essential, and ammonia generated at the crosslinking reaction temperature (40 to 330 ° C.) causes the triazine crosslinking of the non-perfluoro elastomer (A) to cause curing. Therefore, in the present invention, the ammonia generating compound can be used alone to cause curing (triazine crosslinking), but the curing agent (B) can be used in combination to form other crosslinking in addition to the triazine crosslinking. Also good.
  • ammonia generating compound (C) As the ammonia generating compound (C), urea or a derivative thereof and an ammonium salt are preferable, and urea or an ammonium salt is more preferable.
  • the ammonium salt may be an organic ammonium salt or an inorganic ammonium salt.
  • the ammonia generating compound (C) may be one that reacts with a small amount of water to generate ammonia.
  • urea derivatives examples include biurea, thiourea, urea hydrochloride, biuret and the like.
  • organic ammonium salts examples include compounds described in JP-A-9-111101, WO00 / 09603, and WO98 / 23675, such as ammonium perfluorohexanoate and ammonium perfluorooctanoate.
  • Ammonium salt of polyfluorocarboxylic acid ammonium salt of polyfluorosulfonic acid such as ammonium perfluorohexanesulfonate and ammonium perfluorooctanesulfonate; polyfluoroalkyl such as ammonium perfluorohexanephosphate and ammonium perfluorooctanephosphate Group-containing phosphoric acid or phosphonic acid ammonium salt; non-fluorinated carboxylic acid such as ammonium benzoate, ammonium adipate, ammonium phthalate, etc.
  • Ammonium salts of sulfonic acid can be exemplified.
  • a fluorine-based carboxylic acid, a sulfonic acid or an ammonium salt of phosphoric acid is preferable.
  • Ammonium salts of sulfonic acid or phosphoric acid are preferred.
  • Examples of the inorganic ammonium salt include compounds described in JP-A-9-111101, such as ammonium sulfate, ammonium carbonate, ammonium nitrate, and ammonium phosphate. Among them, ammonium phosphate is preferable in view of vulcanization characteristics.
  • acetaldehyde ammonia hexamethylenetetramine, formamidine, formamidine hydrochloride, formamidine acetate, t-butyl carbamate, benzyl carbamate, HCF 2 CF 2 CH (CH 3 ) OCONH 2 , phthalamide and the like can be used.
  • ammonia generating compounds (C) may be used alone or in combination of two or more.
  • the addition amount of the ammonia generating compound (C) may be appropriately selected depending on the amount of ammonia to be generated, but when used alone, it is usually 0.05 to 100 parts by mass of the non-perfluoroelastomer (A). To 10 parts by mass, preferably 0.1 to 5 parts by mass, and more preferably 0.2 to 3 parts by mass. If the amount of the ammonia generating compound is too small, the crosslinking density is lowered, so that there is a tendency that the practically sufficient heat resistance and chemical resistance are not expressed. If the amount is too large, there is a concern of scorching and storage stability is deteriorated. There is a problem and there is a tendency that the color of the molded product is not transparent.
  • the curing agent (B) and the ammonia generating compound (C) may be used in combination.
  • a cross-linked product having excellent mechanical strength, heat resistance, chemical resistance, and cold resistance, and particularly excellent balance between heat resistance and cold resistance is obtained.
  • the amount of the ammonia generating compound (C) to be used in combination with the curing agent (B) may be appropriately selected depending on the amount of generated ammonia, but is usually 100 masses of the specific non-perfluoroelastomer (A). Part by weight, 0.01 to 10 parts by weight, preferably 0.02 to 5 parts by weight, more preferably 0.05 to 3 parts by weight.
  • the ammonia generating compound (C) and the inorganic nitride particles (F) may be used in combination, or the curing agent (B), the ammonia generating compound (C), and the inorganic nitride particles (F). May be used in combination.
  • the inorganic nitride particles (F) are not particularly limited, and examples thereof include silicon nitride (Si 3 N 4 ), lithium nitride, titanium nitride, aluminum nitride, boron nitride, vanadium nitride, and zirconium nitride.
  • silicon nitride particles are preferable from the viewpoint that nano-sized fine particles can be supplied and that they do not contain metals that are hated in the semiconductor manufacturing process.
  • These nitride particles may be used in combination of two or more.
  • the particle size of the inorganic nitride particles (F) is not particularly limited, but is preferably 1000 nm or less, more preferably 300 nm or less, and even more preferably 100 nm or less.
  • the lower limit is not particularly limited.
  • the added amount of the inorganic nitride particles (F) is 0.1 to 20 parts by weight with respect to 100 parts by weight of the non-fluorine perfluoroelastomer (A) when the inorganic nitride particles (F) are used alone. It is preferably 0.2 to 5 parts by weight, more preferably 0.2 to 1 part by weight. If the inorganic nitride particles (F) are less than 0.1 parts by weight, the vulcanization density will be low, so that there is a tendency that practically sufficient heat resistance and chemical resistance will not be expressed, and if the amount exceeds 20 parts by weight. , There is a concern of scorch, there is a problem that storage stability is deteriorated, and there is a tendency that the color of the molded product is not transparent.
  • the added amount of the inorganic nitride particles (F) is 100 parts by weight of the non-fluorine perfluoroelastomer (A).
  • the lower limit is preferably 0.01 to 1 part by weight, more preferably 0.03 part by weight, still more preferably 0.05 part by weight, and the upper limit is more preferably 0.7 part by weight. More preferably, it is 0.5 part by weight.
  • the curable composition of the present invention in a semiconductor manufacturing apparatus or a solar cell manufacturing apparatus, particularly in a heat-resistant component at a location where high purity and non-contamination are not required, the curable composition can be used as necessary.
  • Usable additives such as fillers, processing aids, plasticizers, colorants, stabilizers, adhesion aids, etc. can be blended, and conventional curing agents and crosslinking aids different from those mentioned above One or more may be blended.
  • the filler (D1) improves physical properties such as tensile strength, modulus, hardness and the like of the crosslinked product, and can be added as necessary in the present invention.
  • Examples of the filler (D1) include metal fillers such as metal oxides, metal carbides, metal halides, metal sulfides, metal salts, and metal hydroxides; carbon fillers such as carbon black, graphitized carbon, and graphite. And at least one of organic fillers such as high styrene resin, phenol resin, coumarone resin, polyimide, polyether ether ketone, polyamide imide, polyether sulfone, polyether nitrile, polyether imide, and polyphenylene sulfide.
  • metal fillers such as metal oxides, metal carbides, metal halides, metal sulfides, metal salts, and metal hydroxides
  • carbon fillers such as carbon black, graphitized carbon, and graphite.
  • organic fillers such as high styrene resin, phenol resin, coumarone resin, polyimide, polyether ether ketone, polyamide imide, polyether sulfone, polyether nitrile, poly
  • metal oxide examples include silicon oxide, barium oxide, titanium oxide, aluminum oxide, silver oxide, beryllium oxide, bismuth oxide, chromium oxide, boron oxide, cadmium oxide, copper oxide, iron oxide, gallium oxide, germanium oxide, and oxide.
  • Examples thereof include tantalum oxide, thorium oxide, vanadium oxide, tungsten oxide, zinc oxide, and zirconium oxide, and silicon oxide, titanium oxide, and aluminum oxide are preferable because they are excellent in chemical resistance and chemical stability. From the viewpoint of reinforcement, silicon oxide is particularly preferable.
  • metal carbide examples include boron carbide, calcium carbide, iron carbide, manganese carbide, titanium carbide, silicon carbide, vanadium carbide, and aluminum carbide. From the viewpoint of excellent chemical resistance and chemical stability, carbonization. Silicon and titanium carbide are preferred.
  • metal halides include silver chloride, silver fluoride, aluminum chloride, aluminum fluoride, barium chloride, barium fluoride, calcium chloride, calcium fluoride, cadmium chloride, chromium chloride, cesium chloride, cesium fluoride, and copper chloride.
  • metal chlorides or metal fluorides such as tin, strontium chloride, thallium chloride, vanadium chloride, zinc chloride, zirconium chloride, and bromides or iodides of these, which have low hygroscopicity and excellent chemical stability. From aluminum fluoride, Of barium is preferable.
  • the metal salt is represented by the formula: MnAm (M is a metal, A is a residue of various inorganic acids, m and n are appropriately determined depending on respective valences), for example, sulfates, carbonates of various metals, Examples thereof include phosphate, titanate, silicate, and nitrate.
  • Specific examples include, for example, aluminum sulfate, barium carbonate, silver nitrate, barium nitrate, barium sulfate, barium titanate, calcium carbonate, calcium nitrate, calcium phosphate, calcium silicate, calcium titanate, cadmium sulfate, cobalt sulfate, copper sulfate, carbonate Ferrous iron, iron silicate, iron titanate, potassium nitrate, potassium sulfate, lithium nitrate, magnesium carbonate, magnesium nitrate, magnesium silicate, magnesium titanate, magnesium carbonate, manganese sulfate, manganese silicate, sodium carbonate, sodium nitrate, Sodium sulfate, sodium silicate, sodium titanate, nickel sulfate, lead carbonate, lead sulfate, strontium carbonate, strontium sulfate, strontium titanate, zinc carbonate, zinc sulfate, zinc titanate, etc. From the viewpoint of excellent plasma resistance and
  • metal hydroxide examples include calcium hydroxide and magnesium hydroxide.
  • metal sulfide examples include silver sulfide, calcium sulfide, cadmium sulfide, cobalt sulfide, copper sulfide, iron sulfide, manganese sulfide, molybdenum disulfide, lead sulfide, tin sulfide, zinc sulfide, and tungsten disulfide.
  • Carbon black includes thermal black, bituminous coal filler, furnace black, channel black and the like.
  • a bituminous coal filler is preferable from the viewpoint of compression set resistance of the molded product, and a mixture of bituminous coal filler and thermal black is preferable from the viewpoint of mechanical properties.
  • the added amount of the filler (D1) is preferably 10 to 50 parts by mass with respect to 100 parts by mass of the specific non-perfluoroelastomer (A), from the viewpoint of good mechanical properties of the molded product, From 15 to 45 parts by mass, it is more preferable from the viewpoint of a better balance between the tensile strength and the elongation of the molded product.
  • the mixing weight ratio is preferably 9/95 to 80/20, and preferably 30/70 to 70/30. More preferred. If it is out of the above range, deterioration of compression set resistance and deterioration of compression crack resistance may be observed.
  • the method and order of mixing the components of the curable composition are not particularly limited. For example, although the following method can be illustrated, it is not limited to these.
  • (1-1) A method of simultaneously mixing a specific non-perfluoroelastomer (A), an ammonia generating compound (C) and a curing agent (B).
  • (1-2) A method in which the component (B) and the component (C) are mixed in advance and then mixed with the component (A).
  • (1-3) A method in which a part of the component (A), the component (B), and the component (C) are mixed in advance to form a master batch, and then mixed with the remaining component (A).
  • (1-4) A part of component (A) and component (B) are mixed in advance to form a master batch, and then mixed with the remaining components (A) and (C) (in this case, the remaining (A) ) Component and (C) component may be mixed in advance).
  • the other additive (D) may be blended at any stage in the above methods.
  • filler (D1), (1-5) Component (B) and filler (D1) are mixed in advance to form a master batch, and the remaining components are mixed (in this case, the remaining components are (It may be mixed in advance).
  • the specific non-perfluoroelastomer (A) used for preparing the masterbatch is one of all non-perfluoroelastomers (A) from the viewpoint of improving the dispersibility of the ammonia generating compound (C). ⁇ 50% by weight is preferred.
  • the elastomer used for preparing the masterbatch may not necessarily be the non-perfluoroelastomer (A), and another elastomer such as a scorch during mixing may be used.
  • Such an elastomer that does not have, for example, an elastomer having no cyano group, carboxyl group or alkoxycarbonyl group may be used alone or in combination.
  • VdF type which does not contain monomer (a3) in other VdF type elastomers, for example, VdF type elastomer (A1), from the point of good compatibility with a specific non-perfluoro type elastomer (A).
  • An elastomer or an elastomer of a monomer other than propylene and TFE is preferred.
  • the composition of the master batch is, for example, 5 to 120 parts by mass of the curing agent (B) when adding the curing agent (B) to the master batch with respect to 100 parts by mass of the elastomer for the master batch.
  • blending (C) into the masterbatch it is preferable to blend 5 to 120 parts by mass of the ammonia generating compound (C).
  • Examples of means for mixing the components of the curable composition include ordinary elastomer processing machines such as an open roll, a Banbury mixer, and a kneader.
  • the curable composition of the present invention can be mixed by mixing the components. Can be prepared. In addition, it can be prepared by a method using a closed mixer.
  • the powder of the ammonia generating compound (C) which is a solid substance is directly kneaded with a specific non-perfluoro elastomer (A) with a kneader or an open roll, and the ammonia generating compound (C) is then non-perfluoro elastomer.
  • the non-perfluoroelastomer (A) has high surface slipperiness and it is possible to incorporate the ammonia generating compound (C), but it is not easy to knead and disperse uniformly. Absent.
  • a solvent (E) having an affinity for the ammonia generating compound (C) can be present in the mixing field. That's fine.
  • affinity solvent (E) water (E1) or an organic solvent (E2) having affinity for the ammonia generating compound (C) is preferable.
  • organic solvent (E2) examples include alcohol solvents such as methanol, ethanol and glycerin.
  • water (E1) is preferable because it is inexpensive, easy to handle and remove, and environmentally friendly.
  • the method of causing the affinity solvent (E) to be present in the mixing field is not particularly limited, but from the viewpoint of enhancing the dispersibility of the ammonia generating compound (C), the affinity solvent (E) and the ammonia generation in advance. It is preferable to add to the place of mixing as a liquid mixture with a compound (C).
  • Crosslinking of the curable composition of the present invention can be performed by a usual method such as a method of heat-compressing with a mold, a method of press-fitting into a heated mold, a method of cross-linking after extrusion with an extruder. it can. Crosslinking is usually performed in the order of primary crosslinking and finally secondary crosslinking to obtain a molded product.
  • heating is preferably performed at 150 to 230 ° C. for 5 to 120 minutes, more preferably heating at 160 to 200 ° C. for 5 to 60 minutes, and heating at 170 to 190 ° C. for 5 to 60 minutes. It is particularly preferred to do this.
  • the crosslinking means a known crosslinking means may be used, and examples thereof include press crosslinking.
  • heating at 160 to 320 ° C. for 2 to 24 hours is preferable, and heating at 180 to 310 ° C. for 4 to 20 hours is more preferable.
  • a crosslinking means a known crosslinking means may be used, and examples thereof include oven crosslinking.
  • the heat-resistant part of the present invention can be obtained by crosslinking the curable composition of the present invention.
  • the heat-resistant component of the present invention is excellent in chemical resistance, mechanical strength, heat resistance, compression set, and the like.
  • the heat-resistant component of the present invention exhibits excellent properties such that the compression set is small even after being left at a high temperature as compared with a conventional cross-linked molded product made of a non-perfluoroelastomer. It can be particularly suitably used as a sealing material.
  • the heat-resistant component is preferably a component used at 200 ° C. or higher.
  • heat-resistant components used in semiconductor, liquid crystal, solar battery, or organic EL manufacturing equipment are required to have high-temperature sealing properties, low contamination, low outgassing properties, plasma resistance, etc.
  • the heat-resistant component of the invention satisfies these required characteristics.
  • heat-resistant components used in semiconductor manufacturing apparatuses, liquid crystal manufacturing apparatuses, solar cell manufacturing apparatuses, and organic EL manufacturing apparatuses include various sealing materials such as gaskets, O-rings, square rings, rubber sheets, and joint sheets.
  • the crosslinking conditions employed in the present invention are the following conditions.
  • Standard crosslinking conditions Kneading method: Roll kneading press crosslinking (primary crosslinking): 30 minutes at 180 ° C. (specify if different) Oven crosslinking (secondary crosslinking): 2 hours at 200 ° C., 5 hours at 260 ° C., 18 hours at 300 ° C.
  • ⁇ 100% modulus (M100)> The curable composition shown in Table 1 is subjected to primary press crosslinking and secondary oven crosslinking under standard crosslinking conditions to obtain a sheet having a thickness of 2 mm, and the measurement is performed according to JIS-K6251.
  • Hs Shore A hardness
  • VdF / TFE / HFP 19/11/70 mol% ratio
  • APS ammonium persulfate
  • CF 2 CFOCF 2 CF (CF 3 ) OCF 2 CF 2 CN (CNVE) 1.8 g were injected under nitrogen pressure to initiate the reaction.
  • VdF / HFP 50/50 mol% ratio
  • Example 1 0.4 parts by mass of urea (manufactured by Kishida Chemical Co., Ltd.) and carbon black (CB) (manufactured by Cancarb) with respect to 100 parts by mass of the CN group-containing copolymer (A1-1) obtained in Production Example 1
  • Thermax N990 35 parts by mass was kneaded with an open roll to prepare a curable composition.
  • the obtained composition was cross-linked under the above standard cross-linking conditions to prepare a cross-linked product having a thickness of 2 mm and a test sample of an O-ring (AS-568A-214), 100% modulus, tensile breaking strength and tensile breaking elongation.
  • the Shore A hardness and compression set were measured. The results are shown in Table 1.
  • Example 2 A urea solution was prepared by dissolving 0.4 parts by mass of urea (manufactured by Kishida Chemical Co., Ltd.) in 1 part by mass of water. To 100 parts by mass of the CN group-containing copolymer (A1-1) obtained in Production Example 1, 35 parts by mass of the urea solution prepared above and carbon black (CB) (Thermax N990 manufactured by Cancarb) was blended. The curable composition was prepared by kneading with an open roll. The obtained composition was cross-linked under the above-mentioned standard cross-linking conditions (however, press cross-linking was performed at 180 ° C.
  • CB carbon black
  • Example 3 A curable composition was prepared in the same manner as in Example 1 except that the amount of urea was changed to 0.6 parts by mass, and then crosslinked to give a crosslinked product having a thickness of 2 mm and an O-ring (AS-568A-214).
  • the test samples were prepared and measured for 100% modulus, tensile strength at break, tensile elongation at break, Shore A hardness and compression set. The results are shown in Table 1.
  • Example 4 A curable composition was prepared in the same manner as in Example 1 except that 1.0 part by mass of ammonium perfluorohexanoate was blended in place of urea, and then crosslinked, and a crosslinked product having a thickness of 2 mm and an O-ring (AS A test sample of ⁇ 568A-214) was prepared, and 100% modulus, tensile strength at break, tensile elongation at break, Shore A hardness and compression set were measured. The results are shown in Table 1.
  • Example 5 A curable composition was prepared in the same manner as in Example 4 except that the amount of ammonium perfluorohexanoate was changed to 2.9 parts by mass, and then crosslinked to give a crosslinked product having a thickness of 2 mm and an O-ring (AS- 568A-214), 100% modulus, tensile strength at break, tensile elongation at break, Shore A hardness and compression set were measured. The results are shown in Table 1.
  • Example 6 A curable composition was prepared in the same manner as in Example 1 except that 0.4 parts by mass of ammonium adipate was added instead of urea. The obtained composition was cross-linked under the above-mentioned standard cross-linking conditions (however, press cross-linking was performed at 180 ° C. for 20 minutes) to prepare a 2 mm-thick cross-linked product and an O-ring (AS-568A-214) test sample. Fabricated and measured for 100% modulus, tensile break strength and elongation at break, Shore A hardness and compression set. The results are shown in Table 1.
  • Example 7 With respect to 100 parts by mass of the CN group-containing copolymer (A1-1) obtained in Production Example 1, 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane (OH-AF) is used as a curing agent. ) And 35 parts by mass of carbon black (CB) (Thermax N990 manufactured by Cancarb) were mixed and kneaded with an open roll to prepare a curable composition. The obtained composition was cross-linked under the above-mentioned standard cross-linking conditions to prepare a 2 mm-thick cross-linked product and a test sample of an O-ring (AS-568A-214), 100% modulus, tensile breaking strength, tensile breaking elongation. The Shore A hardness and compression set were measured. The results are shown in Table 1.
  • Example 8 instead of 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane (OH-AF), 2,2-bis (3,4-diaminophenyl) hexafluoropropane (TA-AF)
  • OH-AF 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane
  • TA-AF 2,2-bis (3,4-diaminophenyl) hexafluoropropane
  • a curable composition was prepared in the same manner as in Example 7 except that 8 parts by mass was blended.
  • the obtained composition was cross-linked under the above-mentioned standard cross-linking conditions to prepare a test sample of a cross-linked product having a thickness of 2 mm and an O-ring (AS-568A-214), 100% modulus, tensile breaking strength, tensile breaking elongation, Shore A hardness and compression set were measured. The results are shown in Table 1.
  • Example 9 With respect to 100 parts by mass of the CN group-containing copolymer (A1-1) obtained in Production Example 1, 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane (OH-AF) is used as a curing agent. ), 1.8 parts by mass of urea (manufactured by Kishida Chemical Co., Ltd.), 35 parts by mass of carbon black (CB) (Thermax N990 from Cancarb), and kneaded with an open roll. A curable composition was prepared.
  • urea manufactured by Kishida Chemical Co., Ltd.
  • CB carbon black
  • the obtained composition was cross-linked under the above-mentioned standard cross-linking conditions to prepare a 2 mm-thick cross-linked product and a test sample of an O-ring (AS-568A-214), 100% modulus, tensile breaking strength, tensile breaking elongation.
  • the Shore A hardness and compression set were measured. The results are shown in Table 1.
  • Example 10 instead of 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane (OH-AF), 2,2-bis (3,4-diaminophenyl) hexafluoropropane (TA-AF)
  • OH-AF 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane
  • TA-AF 2,2-bis (3,4-diaminophenyl) hexafluoropropane
  • a curable composition was prepared in the same manner as in Example 9 except that 8 parts by mass was blended.
  • the obtained composition was cross-linked under the above-mentioned standard cross-linking conditions to prepare a test sample of a cross-linked product having a thickness of 2 mm and an O-ring (AS-568A-214), 100% modulus, tensile breaking strength, tensile breaking elongation, Shore A hardness and compression set were measured. The results are shown in Table 1.
  • Example 11 With respect to 100 parts by mass of the CN group-containing copolymer (A1-2) obtained in Production Example 2, 0.4 parts by mass of urea (manufactured by Kishida Chemical Co., Ltd.) and carbon black (CB) (manufactured by Cancarb) Thermax N990) of 35 parts by mass was kneaded with an open roll to prepare a curable composition.
  • the obtained composition was cross-linked under the above-mentioned standard cross-linking conditions to prepare a test sample of a cross-linked product having a thickness of 2 mm and an O-ring (AS-568A-214), 100% modulus, tensile breaking strength, tensile breaking elongation, Shore A hardness and compression set were measured. The results are shown in Table 1.
  • Example 12 0.1 parts by mass of urea (manufactured by Kishida Chemical Co., Ltd.) and 2,2-bis (as a curing agent) with respect to 100 parts by mass of the CN group-containing copolymer (A1-2) obtained in Production Example 2. 1.8 parts by mass of 3,4-diaminophenyl) hexafluoropropane (TA-AF) and 35 parts by mass of carbon black (CB) (Thermax N990 manufactured by Cancarb) are mixed and cured by an open roll. A sex composition was prepared.
  • urea manufactured by Kishida Chemical Co., Ltd.
  • 2,2-bis as a curing agent
  • the obtained composition was cross-linked under the above-mentioned standard cross-linking conditions to prepare a test sample of a cross-linked product having a thickness of 2 mm and an O-ring (AS-568A-214), 100% modulus, tensile breaking strength, tensile breaking elongation, Shore A hardness and compression set were measured. The results are shown in Table 1.
  • Example 13 With respect to 100 parts by mass of the CN group-containing copolymer (A1-2) obtained in Production Example 2, 2,2-bis (3,4-diaminophenyl) hexafluoropropane (TA-AF) is used as a curing agent. 1.8 parts by mass and further 35 parts by mass of carbon black (CB) (Thermax N990 manufactured by Cancarb) were blended and kneaded with an open roll to prepare a curable composition.
  • CB carbon black
  • the obtained composition was cross-linked under the above-mentioned standard cross-linking conditions to prepare a test sample of a cross-linked product having a thickness of 2 mm and an O-ring (AS-568A-214), 100% modulus, tensile breaking strength, tensile breaking elongation, Shore A hardness and compression set were measured. The results are shown in Table 1.
  • Example 14 Compounding 0.5 parts by mass of silicon nitride and 20 parts by mass of carbon black (CB) (Thermax N990 manufactured by Cancarb) with respect to 100 parts by mass of the CN group-containing copolymer (A1-1) obtained in Production Example 1.
  • CB carbon black
  • the mixture was kneaded with an open roll to prepare a curable composition.
  • the obtained composition was crosslinked at 200 ° C. for 8 hours and 290 ° C. for 8 hours (however, press crosslinking was performed at 180 ° C.
  • Example 15 Compounding 20 parts by mass of 1.0 part by mass of silicon nitride and 20 parts by mass of carbon black (CB) (Thermax N990 manufactured by Cancarb) with respect to 100 parts by mass of the CN group-containing copolymer (A1-1) obtained in Production Example 1.
  • the mixture was kneaded with an open roll to prepare a curable composition.
  • the obtained composition was crosslinked at 200 ° C. for 8 hours and 290 ° C. for 8 hours (however, press crosslinking was performed at 180 ° C.
  • Example 16 With respect to 100 parts by mass of the CN group-containing copolymer (A1-1) obtained in Production Example 1, 0.5 part by mass of silicon nitride and 2,2-bis (3-amino-4-hydroxyphenyl) as a curing agent ) 0.5 parts by mass of hexafluoropropane (OH-AF) and 20 parts by mass of carbon black (CB) (Thermax N990 manufactured by Cancarb) were blended and kneaded with an open roll to prepare a curable composition. The obtained composition was crosslinked at 200 ° C. for 8 hours and 290 ° C. for 8 hours (however, press crosslinking was performed at 180 ° C.
  • OH-AF hexafluoropropane
  • CB carbon black
  • Example 17 For 100 parts by mass of the CN group-containing copolymer (A1-1) obtained in Production Example 1, 0.5 part by mass of urea (manufactured by Kishida Chemical Co., Ltd.), 0.5 part by mass of silicon nitride, carbon black 20 parts by mass of (CB) (Thermax N990 manufactured by Cancarb) was blended and kneaded with an open roll to prepare a curable composition. The obtained composition was crosslinked at 200 ° C. for 8 hours and 290 ° C. for 8 hours (however, press crosslinking was performed at 180 ° C.
  • urea manufactured by Kishida Chemical Co., Ltd.
  • CB carbon black 20 parts by mass of
  • the obtained composition was crosslinked at 200 ° C. for 8 hours and 290 ° C. for 8 hours (however, press crosslinking was performed at 180 ° C.
  • a curable composition was prepared by blending parts and kneading with an open roll. Next, this crosslinkable composition was pressed at 160 ° C. for 10 minutes, and further subjected to oven crosslinking in an oven at 200 ° C.

Abstract

L'invention concerne un composant résistant à la chaleur permettant d'améliorer la vitesse de réticulation d'un élastomère non perfluoré qui constitue le composant, et satisfaisant en outre les caractéristiques nécessaires à un élément d'étanchéité, ou similaire, mis en œuvre dans un dispositif de fabrication de semi-conducteurs, de cristaux liquides, de cellules solaires ou d'éléments EL organiques. Plus précisément, l'invention concerne une composition durcissable pour composant résistant à la chaleur dans un dispositif de fabrication de semi-conducteurs, de cristaux liquides, de cellules solaires ou d'éléments EL organiques. Cette composition contient (A) un élastomère de fluorure de vinylidène (A1) (la proportion de fluorure de vinylidène copolymérisé dépassant 20% en moles) consistant en un copolymère de fluorure de vinylidène, d'oléfine perfluorée d'au moins une sorte choisie dans un groupe constitué de tétrafluoroéthylène, hexafluoropropylène et perfluoro(alkylvinyléther), et d'un monomère comprenant un groupe cyano, un groupe carboxyle, et un groupe alcoxycarbonyle; ou un élastomère de tétrafluoro éthylène-propylène (A2) consistant en un copolymère de 40 à 70% en moles de tétrafluoroéthylène, de 30 à 60% en moles de propylène, et d'un monomère comprenant un groupe cyano, un groupe carboxyle, et un groupe alcoxycarbonyle. Cette composition contient également : (B) un agent durcissant, (C) un composé produisant de l'ammoniac entre 40 et 330°C, et/ou (F) des particules de nitrure inorganique.
PCT/JP2011/057673 2010-03-31 2011-03-28 Composition durcissable pour composant résistant à la chaleur de dispositif de fabrication de semi-conducteurs, de cristaux liquides, de cellules solaires ou d'éléments électroluminescents (el) organiques WO2011125614A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2015125726A1 (ja) * 2014-02-18 2017-03-30 ダイキン工業株式会社 パーフルオロエラストマー水性分散液の製造方法及びパーフルオロエラストマーの製造方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09111081A (ja) * 1995-03-31 1997-04-28 Nippon Mektron Ltd 含フッ素エラストマー組成物
JP2004524424A (ja) * 2001-04-12 2004-08-12 スリーエム イノベイティブ プロパティズ カンパニー ペンダントのイミデート構造を有するフルオロポリマー
WO2007013397A1 (fr) * 2005-07-26 2007-02-01 Daikin Industries, Ltd. Composition durcissable, article moulé obtenu à partir de celle-ci et procédé servant à produire un article moulé

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09111081A (ja) * 1995-03-31 1997-04-28 Nippon Mektron Ltd 含フッ素エラストマー組成物
JP2004524424A (ja) * 2001-04-12 2004-08-12 スリーエム イノベイティブ プロパティズ カンパニー ペンダントのイミデート構造を有するフルオロポリマー
WO2007013397A1 (fr) * 2005-07-26 2007-02-01 Daikin Industries, Ltd. Composition durcissable, article moulé obtenu à partir de celle-ci et procédé servant à produire un article moulé

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2015125726A1 (ja) * 2014-02-18 2017-03-30 ダイキン工業株式会社 パーフルオロエラストマー水性分散液の製造方法及びパーフルオロエラストマーの製造方法

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