WO2021200871A1 - 半硬化物複合体及びその製造方法、硬化物複合体及びその製造方法、並びに多孔質体に含浸させて用いられる熱硬化性組成物 - Google Patents

半硬化物複合体及びその製造方法、硬化物複合体及びその製造方法、並びに多孔質体に含浸させて用いられる熱硬化性組成物 Download PDF

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WO2021200871A1
WO2021200871A1 PCT/JP2021/013397 JP2021013397W WO2021200871A1 WO 2021200871 A1 WO2021200871 A1 WO 2021200871A1 JP 2021013397 W JP2021013397 W JP 2021013397W WO 2021200871 A1 WO2021200871 A1 WO 2021200871A1
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Prior art keywords
compound
thermosetting composition
cured product
porous body
semi
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Ceased
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PCT/JP2021/013397
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English (en)
French (fr)
Japanese (ja)
Inventor
絵梨 金子
麻菜 大木
紗緒梨 井之上
幸治 辻
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Denka Co Ltd
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Denka Co Ltd
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Application filed by Denka Co Ltd filed Critical Denka Co Ltd
Priority to EP21780239.6A priority Critical patent/EP4130114A4/en
Priority to JP2022512245A priority patent/JP7622041B2/ja
Priority to CN202180023020.9A priority patent/CN115315470A/zh
Priority to US17/907,462 priority patent/US20230122917A1/en
Publication of WO2021200871A1 publication Critical patent/WO2021200871A1/ja
Anticipated expiration legal-status Critical
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    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/009—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone characterised by the material treated
    • C—CHEMISTRY; METALLURGY
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    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
    • C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
    • C04B41/48—Macromolecular compounds
    • C04B41/4853—Epoxides
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    • C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
    • C04B35/515—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics
    • C04B35/58—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on borides, nitrides, i.e. nitrides, oxynitrides, carbonitrides or oxycarbonitrides or silicides
    • C04B35/583—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on borides, nitrides, i.e. nitrides, oxynitrides, carbonitrides or oxycarbonitrides or silicides based on boron nitride
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    • C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
    • C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
    • C04B35/64—Burning or sintering processes
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    • C04B38/00—Porous mortars, concrete, artificial stone or ceramic ware; Preparation thereof
    • C04B38/0038—Porous mortars, concrete, artificial stone or ceramic ware; Preparation thereof by superficial sintering or bonding of particulate matter
    • C—CHEMISTRY; METALLURGY
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    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/0072—Heat treatment
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    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/80—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone of only ceramics
    • C04B41/81—Coating or impregnation
    • C04B41/82—Coating or impregnation with organic materials
    • C04B41/83—Macromolecular compounds
    • C—CHEMISTRY; METALLURGY
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • C08G59/4223—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof aromatic
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    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/5046—Amines heterocyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C08G59/681—Metal alcoholates, phenolates or carboxylates
    • C08G59/682—Alcoholates
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
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    • C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
    • C04B2111/00474—Uses not provided for elsewhere in C04B2111/00
    • C04B2111/00844—Uses not provided for elsewhere in C04B2111/00 for electronic applications
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    • C04B2235/00—Aspects relating to ceramic starting mixtures or sintered ceramic products
    • C04B2235/02—Composition of constituents of the starting material or of secondary phases of the final product
    • C04B2235/30—Constituents and secondary phases not being of a fibrous nature
    • C04B2235/38—Non-oxide ceramic constituents or additives
    • C04B2235/3852—Nitrides, e.g. oxynitrides, carbonitrides, oxycarbonitrides, lithium nitride, magnesium nitride
    • C04B2235/386—Boron nitrides
    • C—CHEMISTRY; METALLURGY
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    • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10H—INORGANIC LIGHT-EMITTING SEMICONDUCTOR DEVICES HAVING POTENTIAL BARRIERS
    • H10H20/00—Individual inorganic light-emitting semiconductor devices having potential barriers, e.g. light-emitting diodes [LED]
    • H10H20/80—Constructional details
    • H10H20/85—Packages
    • H10H20/858—Means for heat extraction or cooling
    • H10H20/8583—Means for heat extraction or cooling not being in contact with the bodies

Definitions

  • the present invention relates to a semi-cured product composite and a method for producing the same, a cured product composite and a method for producing the same, and a thermosetting composition used by impregnating a porous body.
  • the above-mentioned composite is used by being adhered to an adherend such as an electronic component, it is desirable that a highly adhesive state can be maintained for a long time because it is excellent in handleability.
  • the resin is in a semi-cured state, and when it is in a predetermined viscosity range, it is in a state of excellent adhesiveness.
  • it is difficult to keep the resin in a desired viscosity range because a rapid increase in viscosity is likely to occur in the semi-cured resin.
  • One aspect of the present invention is to hold the semi-cured product in a desired viscosity range in the semi-cured product composite in which the porous body is impregnated with the semi-cured product of the thermosetting composition.
  • the present inventors hold a semi-cured product of a thermosetting composition containing a predetermined amount of an epoxy compound and a cyanate compound in a desired viscosity range (for example, a viscosity range having excellent adhesiveness) without a rapid increase in viscosity. Found to be done. As a result, it was found that the semi-cured product composite obtained by impregnating the porous body with the semi-cured product of this curable composition can maintain a highly adhesive state, and completed the present invention.
  • a desired viscosity range for example, a viscosity range having excellent adhesiveness
  • thermosetting composition impregnated in the porous body, wherein the thermosetting composition is an epoxy compound.
  • thermosetting composition is an epoxy compound.
  • a semi-cured product composite containing a cyanate compound and having an equivalent ratio of an epoxy group of an epoxy compound to a cyanato group of the cyanate compound of 1.0 or more in a thermosetting composition.
  • the cyanate compound can be added to the complex to increase its heat resistance, but on the other hand, a rapid increase in viscosity of the semi-cured resin is likely to occur.
  • the cyanate compound and the epoxy compound are contained in a predetermined balance, so that a rapid increase in viscosity of the semi-cured product can be suppressed.
  • Another aspect of the present invention is a step of impregnating a porous body with a thermosetting composition containing an epoxy compound and a cyanate compound, and a reaction of the cyanate compound with the porous body impregnated with the thermosetting composition.
  • a method for producing a semi-cured product composite which comprises a step of heating at a temperature of T1 and a thermosetting composition in which the equivalent ratio of the epoxy group of the epoxy compound to the cyanato group is 1.0 or more. ..
  • thermosetting composition is an epoxy compound
  • a cured product composite containing a cyanate compound and having an equivalent ratio of an epoxy group of an epoxy compound to a cyanato group of 1.0 or more in a thermosetting composition.
  • thermosetting composition containing an epoxy compound and a cyanate compound, and a reaction of the cyanate compound with the porous body impregnated with the thermosetting composition.
  • the equivalent ratio of the epoxy group of the epoxy compound to the cyanato group is 1.0 or more.
  • a method for producing a cured product composite is provided.
  • thermosetting composition used by impregnating a porous body, wherein the thermosetting composition contains an epoxy compound and a cyanate compound, and the cyanato group of the cyanate compound is opposed to the thermosetting composition.
  • the thermosetting composition in which the epoxy group equivalent ratio of the epoxy compound is 1.0 or more.
  • the semi-cured product can be held in a desired viscosity range in the semi-cured product composite in which the porous body is impregnated with the semi-cured product of the thermosetting composition.
  • thermosetting composition which concerns on Example and Comparative Example.
  • the semi-cured product composite includes a porous body and a semi-cured product of a thermosetting composition impregnated in the porous body.
  • the porous body has a structure in which a plurality of fine pores (hereinafter, also referred to as "pores") are formed. At least a part of the pores in the porous body may be connected to each other to form continuous pores.
  • the porous body may be formed of an inorganic compound, and is preferably formed of a sintered body of an inorganic compound.
  • the sintered body of the inorganic compound may be a sintered body of an insulating material.
  • the insulator in the sintered body of the insulator preferably contains a non-oxide such as a carbide, a nitride, diamond, and graphite, and more preferably contains a nitride.
  • the carbide may be silicon carbide or the like.
  • the nitride may contain at least one nitride selected from the group consisting of boron nitride, aluminum nitride, and silicon nitride, and preferably contains boron nitride.
  • the porous body may be preferably formed of a sintered body of an insulating material containing boron nitride, and more preferably formed of a boron nitride sintered body.
  • the boron nitride sintered body may be one obtained by sintering primary particles of boron nitride.
  • the boron nitride either amorphous boron nitride or hexagonal boron nitride can be used.
  • the thermal conductivity of the porous body may be, for example, 30 W / (m ⁇ K) or more, 50 W / (m ⁇ K) or more, or 60 W / (m ⁇ K) or more.
  • the thermal conductivity of the porous body is measured by a laser flash method on a sample in which the porous body is formed to have a length of 10 mm, a width of 10 mm, and a thickness of 1 mm.
  • the average pore diameter of the pores in the porous body may be, for example, 0.5 ⁇ m or more, and is preferably 0.6 ⁇ m or more, more preferably 0, from the viewpoint that the thermosetting composition can be suitably filled in the pores. It is 0.8 ⁇ m or more, more preferably 1 ⁇ m or more.
  • the average pore diameter of the pores is preferably 3.5 ⁇ m or less, 3.0 ⁇ m or less, 2.5 ⁇ m or less, 2.0 ⁇ m or less, or 1.5 ⁇ m or less from the viewpoint of improving the insulating property of the semi-cured composite. be.
  • the average pore size of the pores in the porous body is such that the cumulative pore volume is the total pore volume in the pore size distribution (horizontal axis: pore diameter, vertical axis: cumulative pore volume) measured using a mercury porosimeter. It is defined as a pore size that reaches 50%.
  • a mercury porosimeter a mercury porosimeter manufactured by Shimadzu Corporation can be used, and the measurement is performed by pressurizing while increasing the pressure from 0.03 atm to 4000 atm.
  • the ratio of pores to the porous body is preferably based on the total volume of the porous body from the viewpoint of preferably improving the strength of the semi-cured product composite by filling with the thermosetting composition. Is 10% by volume or more, 20% by volume or more, or 30% by volume or more, preferably 70% by volume or less, more preferably 60% by volume, from the viewpoint of improving the insulating property and thermal conductivity of the semi-cured composite. Hereinafter, it is more preferably 50% by volume or less.
  • the proportion of the porous body in the semi-cured product composite is preferably 30% by volume or more, more preferably 40% by volume or more, still more preferably 40% by volume or more, from the viewpoint of improving the insulating property and thermal conductivity of the semi-cured product composite. It is 50% by volume or more.
  • the proportion of the porous body in the semi-cured product composite may be, for example, 90% by volume or less, 80% by volume or less, 70% by volume or less, or 60% by volume or less.
  • thermosetting composition contains an epoxy compound and a cyanate compound as a thermosetting compound.
  • an epoxy compound having a desired viscosity as a semi-cured product or an epoxy compound having a viscosity suitable for impregnation when impregnating a porous body may be appropriately selected.
  • the epoxy compound include 1,6-bis (2,3-epoxypropan-1-yloxy) naphthalene, bisphenol A type epoxy resin, bisphenol F type epoxy resin, dicyclopentadiene type epoxy resin and the like.
  • 1,6-bis (2,3-epoxypropane-1-yloxy) naphthalene is commercially available, for example, as HP-4032D (trade name, manufactured by DIC Corporation).
  • EP-4000L, EP4088L, EP3950 (above, ADEKA Corporation, trade name), EXA-850CRP (DIC Corporation, trade name), jER807, jER152, YX8000, YX8800 (above, Mitsubishi Chemical Corporation, trade name) is used.
  • an epoxy compound having a vinyl group can also be used.
  • the epoxy compound having a vinyl group include TEPIC-FL, TEPIC-VL (above, manufactured by Nissan Chemical Industries, Ltd., trade name), MA-DGIC, DA-MGIC (above, manufactured by Shikoku Chemicals Corporation, trade name). Etc. are commercially available.
  • the content of the epoxy compound is preferably 30% by mass or more, more preferably 40% by mass or more, still more preferably 50% by mass or more, preferably 85% by mass or less, more preferably 85% by mass or more, based on the total amount of the thermosetting composition. Is 75% by mass or less, more preferably 70% by mass or less.
  • cyanate compound examples include dimethylmethylenebis (1,4-phenylene) biscyanate and bis (4-cyanatephenyl) methane.
  • Dimethylmethylenebis (1,4-phenylene) biscyanate is commercially available, for example, as TA-CN (manufactured by Mitsubishi Gas Chemical Company, Inc., trade name).
  • the content of the cyanate compound is preferably 5% by mass or more, more preferably 8% by mass or more, still more preferably 10% by mass or more, and preferably 51% by mass or less, more preferably 51% by mass or more, based on the total amount of the thermosetting composition. Is 40% by mass or less, more preferably 30% by mass or less.
  • the equivalent ratio of the epoxy group of the epoxy compound to the cyanato group of the cyanate compound contained in the thermosetting composition is 1.0 or more.
  • the corresponding amount ratio is preferably 1.5 or more, more preferably 2.0 or more, still more preferably 2.5 or more, from the viewpoint of facilitating impregnation with the thermosetting composition, and the semi-cured product composite.
  • From the viewpoint of improving heat resistance preferably 6.0 or less, 5.5 or less, 5.0 or less, 4.5 or less, 4.0 or less, 3.5 or less, or 3.0 or less. be.
  • thermosetting composition may further contain other compounds having thermosetting properties other than the epoxy compound and the cyanate compound.
  • thermosetting composition may further contain a curing agent in addition to the epoxy compound and the cyanate compound from the viewpoint of making it easier to maintain the semi-cured state of the desired viscosity.
  • the thermosetting composition contains a curing agent of an epoxy compound.
  • the curing agent for the epoxy compound is a compound that forms a crosslinked structure with the epoxy compound (cures the epoxy compound).
  • the epoxy compound curing agent preferably contains at least one selected from the group consisting of benzoxazine compounds, ester compounds, and phenol compounds.
  • benzoxazine compound examples include bisphenol F-type benzoxazine compounds.
  • the bisphenol F-type benzoxazine compound is commercially available, for example, as FA-type benzoxazine (manufactured by Shikoku Chemicals Corporation, trade name).
  • ester compound examples include diphenyl phthalate and benzyl 2-ethylhexyl phthalate.
  • the ester compound may be an active ester compound.
  • the active ester compound is a compound having one or more ester bonds in the structure and having aromatic rings bonded to both sides of the ester bond.
  • phenol compound examples include phenol, cresol, bisphenol A, bisphenol F, phenol novolac resin, cresol novolac resin, dicyclopentadiene-modified phenol resin, terpene-modified phenol resin, triphenol methane-type resin, and phenol aralkyl resin (phenylene skeleton, biphenylene skeleton). , Etc.), naphthol aralkyl resin, allylphenol resin and the like. These may be used alone or in admixture of two or more.
  • Phenolic compounds are commercially available, for example, as TD2131, VH4150 (manufactured by DIC Corporation, trade name), MEHC-7851M, MEHC-7500, MEH8005, MEH8000H (manufactured by Meiwa Kasei Co., Ltd., trade name).
  • the content of the curing agent is preferably 0.1% by mass or more, more preferably 5% by mass or more, and further, based on the total amount of the thermosetting composition. It is preferably 7% by mass or more, preferably 30% by mass or less, more preferably 20% by mass or less, and further preferably 15% by mass or less.
  • the thermosetting composition may further contain a curing accelerator in addition to the above-mentioned compounds.
  • the curing accelerator contains a component (catalytic type curing agent) that functions as a catalyst for the curing reaction.
  • a component catalytic type curing agent
  • the reaction between the epoxy compound and the cyanate compound, the self-polymerization reaction of the epoxy compound, and / or the reaction between the epoxy compound and the curing agent of the epoxy compound are promoted, which will be described later. It can be facilitated, and the semi-cured product can be easily maintained in a semi-cured state having a desired viscosity.
  • Such a component examples include an organometallic salt, a phosphorus compound, an imidazole derivative, an amine compound, a cationic polymerization initiator and the like.
  • an organometallic salt examples include an organometallic salt, a phosphorus compound, an imidazole derivative, an amine compound, a cationic polymerization initiator and the like.
  • the curing agent these may be used alone or in combination of two or more.
  • Organic metal salts include organic bis (2,4-pentandionato) zinc (II), zinc octylate, zinc naphthenate, cobalt naphthenate, copper naphthenate, iron acetylacetone, nickel octylate, manganese octylate and the like. Examples include metal salts.
  • Phosphorus compounds include tetraphenylphosphonium tetra-p-tolylbolate, tetraphenylphosphonium tetraphenylborate, triphenylphosphine, tri-p-tolylphosphine, tris (4-chlorophenyl) phosphine, and tris (2,6-dimethoxyphenyl).
  • Examples thereof include phosphine, triphenylphosphine triphenylborane, tetraphenylphosphonium disianamide, tetraphenylphosphonium tetra (4-methylphenyl) borate and the like.
  • imidazole derivative examples include 1- (1-cyanomethyl) -2-ethyl-4-methyl-1H-imidazole, 2-ethyl-4-methylimidazole, 2-methylimidazole, 2-phenylimidazole, 1-cyanoethyl-2-phenyl.
  • Amine compounds include dicyandiamide, triethylamine, tributylamine, tri-n-octylamine, 1,4-diazabicyclo [2.2.2] octane, 1,8-diazabicyclo [5.4.0] undec-7-ene. , Benzyldimethylamine, 4-methyl-N, N-dimethylbenzylamine, 2,4,6-tris (dimethylaminomethyl) phenol, 4-dimethylaminopyridine and the like.
  • Examples of the cationic polymerization initiator include benzylsulfonium salt, benzylammonium salt, benzylpyridinium salt, benzylphosphonium salt, hydrazinium salt, carboxylic acid ester compound, sulfonic acid ester compound, amineimide, antimony chloride-acetyl complex chloride, and diallyliodonium salt. Examples thereof include dibenzyloxy copper.
  • the content of the above-mentioned curing accelerator is 0.001 part by mass or more, 0.01 part by mass or more, or 0.05 part by mass with respect to 100 parts by mass in total of the epoxy compound, the cyanate compound, and the curing agent of the epoxy compound. It may be 1 part by mass or less, 0.8 part by mass or less, 0.5 part by mass or less, 0.3 part by mass or less, or 0.1 part by mass or less.
  • the content of the curing accelerator is in this range, the semi-cured product can be easily maintained at a desired viscosity.
  • the semi-cured product composite includes the semi-cured product of the thermosetting composition described above.
  • the semi-cured product of the thermosetting composition (also simply referred to as "semi-cured product”) refers to a cured product in a state in which the curing reaction of the thermosetting composition has partially progressed.
  • the semi-cured product contains a reaction product (cured product) of an epoxy compound and a cyanate compound, and an uncured epoxy compound.
  • the semi-cured product may contain a part of an uncured cyanate compound, or may contain a part of a cured product of an epoxy compound (for example, a cured product obtained by curing an epoxy compound by a self-polymerization reaction). ..
  • the inclusion of the semi-cured product in the semi-cured product composite can be confirmed by measuring the adhesive strength of the semi-cured product composite measured by the following method.
  • the semi-cured product composite is formed into a sheet by the method described later, the sheet is placed between two copper plates, heated and pressurized for 5 minutes under the conditions of 200 ° C. and 10 MPa, and further 200 ° C. and A laminate is obtained by heating under atmospheric pressure conditions for 2 hours.
  • a 90 ° peeling test is performed according to JIS K 6854-1: 1999 "Adhesive-Peeling Adhesive Strength Test Method", and the area of the cohesive fracture portion is measured.
  • the area of the coagulated fracture portion is 30 area% or more, it can be said that the semi-cured product composite contains the semi-cured product.
  • the method for producing a semi-cured compound is a step of impregnating a porous body with a thermosetting composition containing an epoxy compound and a cyanate compound (impregnation step) and a step of impregnating the thermosetting composition. It is provided with a step (semi-curing step) of heating the porous body at a temperature T1 at which the cyanate compound reacts.
  • the aspects of the thermosetting composition are as described above.
  • the impregnation step in one embodiment, first, the above-mentioned porous body is prepared.
  • the porous body may be produced by sintering the raw material or the like, or a commercially available product may be used.
  • the porous body is a sintered body of an inorganic compound
  • the porous body can be obtained by sintering the powder containing the inorganic compound.
  • the impregnation step includes a step of sintering a powder containing an inorganic compound (hereinafter, also referred to as an inorganic compound powder) to obtain a sintered body of an inorganic compound which is a porous body.
  • a slurry containing the powder of the inorganic compound may be spheroidized by a spray dryer or the like, further molded, and then sintered to prepare a sintered body which is a porous body.
  • a mold may be used for molding, or a cold isotropic pressing (CIP) method may be used.
  • a sintering aid may be used.
  • the sintering aid may be, for example, an oxide of a rare earth element such as itria oxide, alumina oxide and magnesium oxide, a carbonate of an alkali metal such as lithium carbonate and sodium carbonate, and boric acid.
  • the amount of the sintering aid added is, for example, 0.01 part by mass or more or 0.1 part by mass with respect to 100 parts by mass of the total of the inorganic compound and the sintering aid. That may be the above.
  • the amount of the sintering aid added may be 20 parts by mass or less, 15 parts by mass or less, or 10 parts by mass or less with respect to 100 parts by mass of the total of the inorganic compound and the sintering aid.
  • the sintering temperature of the inorganic compound may be, for example, 1600 ° C. or higher or 1700 ° C. or higher.
  • the sintering temperature of the inorganic compound may be, for example, 2200 ° C. or lower, or 2000 ° C. or lower.
  • the sintering time of the inorganic compound may be, for example, 1 hour or more and 30 hours or less.
  • the atmosphere at the time of sintering may be, for example, an atmosphere of an inert gas such as nitrogen, helium, or argon.
  • a batch type furnace, a continuous type furnace, or the like can be used.
  • the batch type furnace include a muffle furnace, a tube furnace, an atmosphere furnace, and the like.
  • the continuous furnace include a rotary kiln, a screw conveyor furnace, a tunnel furnace, a belt furnace, a pusher furnace, a koto-shaped continuous furnace, and the like.
  • the porous body may be formed into a desired shape and thickness by cutting or the like, if necessary, before the impregnation step.
  • thermosetting composition a solution containing the thermosetting composition is subsequently prepared in the impregnation device, and the porous body is immersed in the solution to impregnate the pores of the porous body with the thermosetting composition. ..
  • the impregnation step may be performed under either a reduced pressure condition or a pressurized condition, and the impregnation under the reduced pressure condition and the impregnation under the pressurized condition may be performed in combination.
  • the pressure in the impregnation device when the impregnation step is carried out under reduced pressure conditions may be, for example, 1000 Pa or less, 500 Pa or less, 100 Pa or less, 50 Pa or less, or 20 Pa or less.
  • the pressure in the impregnation device may be, for example, 1 MPa or more, 3 MPa or more, 10 MPa or more, or 30 MPa or more.
  • the thermosetting composition When impregnating the porous body with the thermosetting composition, the thermosetting composition may be heated. By heating the thermosetting composition, the viscosity of the solution is adjusted and impregnation into the porous body is promoted.
  • the temperature at which the thermosetting composition is heated for impregnation may be a temperature exceeding the temperature T1 described later. In this case, the temperature at which the thermosetting composition is heated for impregnation may be lower than the temperature T2 in the curing step described later.
  • the upper limit of the temperature at which the thermosetting composition is heated may be equal to or lower than the temperature of T1 + 20 ° C.
  • the porous body is kept immersed in a solution containing a thermosetting composition for a predetermined time.
  • the predetermined time is not particularly limited, and may be, for example, 5 minutes or more, 30 minutes or more, 1 hour or more, 5 hours or more, 10 hours or more, 100 hours or more, or 150 hours or more.
  • the porous body impregnated with the thermosetting composition is heated at the temperature T1 at which the cyanate compound reacts.
  • the cyanate compound contained in the thermosetting composition reacts to obtain a semi-cured product.
  • the cyanate compounds may react with each other, and the cyanate compound may react with a part of the epoxy compound.
  • the equivalent ratio of the epoxy group of the epoxy compound to the cyanate group of the cyanate compound is 1.0 or more. That is, in the semi-cured product, the epoxy compound is contained in excess of the cyanate compound as the epoxy equivalent, and these epoxy compounds remain in an uncured state. As a result, a semi-cured product of the thermosetting composition is obtained.
  • the temperature T1 is preferably 70 ° C. or higher, more preferably 80 ° C. or higher, still more preferably 90 ° C. or higher, from the viewpoint of sufficiently impregnating the porous body with the semi-cured product.
  • the temperature T1 is preferably 180 ° C. or lower, more preferably 150 ° C. or lower, still more preferably 120 ° C. or lower, from the viewpoint of reducing the change in viscosity with time.
  • the temperature T1 refers to the atmospheric temperature at which the porous body impregnated with the thermosetting composition is heated.
  • the heating time in the semi-curing step may be 1 hour or more, 3 hours or more, or 5 hours or more, and may be 12 hours or less, 10 hours or less, or 8 hours or less.
  • thermosetting composition is more adherent to the adherend than the completely cured cured product.
  • this semi-cured product composite is excellent in an adherend to an adherend because the uncured state is maintained for a long period of time unless the uncured compound is heated at a curing temperature (details will be described later).
  • the desired viscosity can be easily maintained.
  • a semi-cured product composite having excellent handleability can be obtained.
  • the cured product composite can be obtained by heating the semi-cured product composite described above at a temperature higher than the temperature T1. That is, the cured product composite according to one embodiment includes a porous body and a cured product of a thermosetting composition impregnated in the porous body.
  • the thermosetting composition is the same as the above-described embodiment.
  • the method for producing a cured product composite includes a step of impregnating a porous body with a thermosetting composition containing an epoxy compound and a cyanate compound (impregnation step), and a step of impregnating the thermosetting composition.
  • the porous body is heated at a temperature T1 at which the epoxy compound and the cyanate compound react, and then heated at a temperature T2 higher than the temperature T1 (curing step).
  • the impregnation step is the same as the above-described embodiment.
  • the porous body impregnated with the thermosetting composition is heated at the temperature T1 at which the cyanate compound reacts.
  • the heating conditions at this time may be the same conditions as the semi-curing step in the method for producing a semi-cured product composite described above.
  • the porous body is heated at a temperature T2 higher than the temperature T1.
  • the temperature T2 may be the temperature at which the epoxy compound self-polymerization reaction (reaction between uncured epoxy compounds) occurs.
  • the uncured epoxy compound contained in the semi-cured product can be cured by the self-polymerization reaction, and the thermosetting composition can be completely cured.
  • the temperature T2 may be a temperature at which the epoxy compound and the epoxy compound curing agent react with each other.
  • the epoxy compound and the curing agent react with each other to form a crosslinked structure, and the thermosetting composition can be completely cured.
  • the temperature T2 is preferably 150 ° C. or higher, more preferably 180 ° C. or higher, and further preferably 200 ° C. or higher from the viewpoint of short-time curing.
  • the temperature T2 is preferably 260 ° C. or lower, more preferably 240 ° C. or lower, still more preferably 220 ° C. or lower, from the viewpoint of volatilization of low molecular weight components contained in the composition and thermal stability of the composition.
  • the temperature T2 refers to the atmospheric temperature when heating the semi-cured product composite.
  • the heating time at the temperature T2 may be 1 hour or more, 5 hours or more, or 10 hours or more, and may be 30 hours or less, 25 hours or less, or 20 hours or less.
  • thermosetting composition preferably used by impregnating a porous body.
  • the thermosetting composition used by impregnating the porous body contains an epoxy compound and a cyanate compound, and the equivalent ratio of the epoxy group of the epoxy compound to the cyanate group of the cyanate compound is 1.0 or more. It is a thermosetting composition.
  • This thermosetting composition is excellent for a complex that can maintain a highly adhesive state by impregnating a porous body and semi-curing it. More specific embodiments of the thermosetting composition are as described above.
  • the semi-cured product composite described above can be used, for example, by molding it into a sheet or the like and adhering it to an adherend.
  • a semi-cured product complex is obtained by the method described above, the resin (thermosetting composition or semi-cured product) adhering to the outer periphery of the complex is removed, and then the semi-cured product is cut to a predetermined thickness.
  • the cured product complex can be formed into a sheet.
  • the semi-cured product composite molded into a sheet shape can be placed on the adherend and pressed while heating at a temperature of T2, for example, to cure the semi-cured product while adhering to the adherend. ..
  • thermosetting composition Epoxy compound: trade name "HP-4032D”, cyanate compound manufactured by DIC Co., Ltd .: trade name "TA-CN”, benzoxazine compound manufactured by Mitsubishi Gas Chemical Co., Ltd .: trade name "FA type benzoxazine”, Shikoku Kasei Kogyo Ester compound manufactured by Co., Ltd .: Diphenyl phthalate, manufactured by Tokyo Kasei Kogyo Co., Ltd. (reagent) Metallic curing accelerator: Bis (2,4-pentandionato) Zinc (II), manufactured by Tokyo Chemical Industry Co., Ltd. Amine-based curing accelerator: 4-dimethylaminopyridine (DMAP), manufactured by Tokyo Chemical Industry Co., Ltd.
  • DMAP 4-dimethylaminopyridine
  • thermosetting composition An epoxy compound, a cyanate compound, and a benzoxazine compound or an ester compound as a curing agent for the epoxy compound were measured in a container so as to have the composition (parts by mass) shown in Table 1. Further, a curing accelerator was added in an amount shown in Table 1 with respect to a total of 100 parts by mass of the epoxy compound, the cyanate compound and the curing agent of the epoxy compound, and all of them were mixed. Since the epoxy compound was in a solid state at room temperature, the epoxy compound was mixed in a state of being heated to about 80 ° C. As a result, the thermosetting compositions according to Examples and Comparative Examples were prepared.
  • thermosetting compositions according to Examples and Comparative Examples were heated and cured under the conditions of 120 ° C. and atmospheric pressure. At the same time as heating, the viscosity of the thermocurable composition changes with respect to the heating time by measuring the viscosity of the thermocurable composition under the condition of a shear rate of 10 (1 / sec) using a rotational viscometer. Was evaluated. The results are shown in FIG. 1 (a) shows the results of Examples 1, 2 and 4, and FIG. 1 (b) shows the results of Example 3. For comparison, both FIGS. 1 (a) and 1 (b) are shown. The result of Comparative Example 1 is shown in. As shown in FIGS.
  • thermosetting compositions of Examples 1 to 4 are thermosetting when heated at 120 ° C. (corresponding to the temperature T1 in the above-described embodiment) for a predetermined time.
  • the viscosity of the composition was substantially constant within the range of 1 ⁇ 10 3 to 1 ⁇ 10 5 Pa ⁇ s. That is, by using a thermosetting composition containing an epoxy compound and a cyanate compound so that the epoxy group equivalent / cyanato group equivalent is 1.0 or more, the heat of Comparative Example 1 in which the equivalent ratio is less than 1.0. It was found that the semi-cured product of the thermosetting composition can be easily adjusted to a state of excellent adhesiveness as compared with the case where the curable composition is used.
  • thermosetting composition of Example 4 since a benzoxazine compound that reacts at a temperature higher than 120 ° C. was added in a larger amount than in Example 1, a larger amount of unreacted epoxy compound remained, and 1 ⁇ viscosity in the following 10 6 Pa ⁇ s becomes substantially constant.
  • Amorphous boron nitride powder (manufactured by Denka Co., Ltd., oxygen content: 1.5%, boron nitride purity 97.6%, average particle size: 6.0 ⁇ m) is 40.0% by mass, hexagonal boron nitride powder in a container. (Manufactured by Denka Co., Ltd., oxygen content: 0.3%, boron nitride purity: 99.0%, average particle size: 30.0 ⁇ m) were measured so as to be 60.0% by mass, and the sintering aid was added. After adding (boric acid, calcium carbonate), an organic binder and water were added and mixed, and then dry granulation was performed to prepare a mixed powder of nitride.
  • the above mixed powder was filled in a mold and press-molded at a pressure of 5 MPa to obtain a molded product.
  • the molded product was compressed by applying a pressure of 20 to 100 MPa using a cold isotropic pressurizing (CIP) device (manufactured by Kobe Steel, Ltd., trade name: ADW800).
  • CIP cold isotropic pressurizing
  • a porous body is prepared by holding the compressed molded body at 2000 ° C. for 10 hours and sintering it using a batch type high-frequency furnace (manufactured by Fuji Dempa Kogyo Co., Ltd., trade name: FTH-300-1H). bottom.
  • the firing was carried out by adjusting the inside of the furnace under a nitrogen atmosphere while flowing nitrogen into the furnace in a standard state so that the flow rate was 10 L / min.
  • the porous body prepared as described above was impregnated with the thermosetting compositions according to Examples 1 to 4 by the following methods.
  • a vacuum heating impregnation device manufactured by Kyoshin Engineering Co., Ltd., trade name: G-555AT-R.
  • the inside of the apparatus was degassed for 10 minutes under the conditions of temperature: 100 ° C. and pressure: 15 Pa.
  • the container containing the porous body and the thermosetting composition was taken out and placed in a pressure heating impregnation device (manufactured by Kyoshin Engineering Co., Ltd., trade name: HP-4030AA-H45) at a temperature of 130 ° C.
  • the thermosetting composition was further impregnated into the porous body by holding for 120 minutes under the condition of 3.5 MPa.
  • the nitride sintered body was taken out from the apparatus and heated under the conditions of a temperature of 120 ° C. and an atmospheric pressure for a predetermined time, so that a semi-cured product composite having excellent adhesiveness could be easily produced.

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PCT/JP2021/013397 2020-03-31 2021-03-29 半硬化物複合体及びその製造方法、硬化物複合体及びその製造方法、並びに多孔質体に含浸させて用いられる熱硬化性組成物 Ceased WO2021200871A1 (ja)

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JP7562351B2 (ja) 2020-09-23 2024-10-07 コニシ株式会社 常温液状の無溶剤型熱硬化性組成物の製造方法
JPWO2022210869A1 (https=) * 2021-03-31 2022-10-06
WO2022210869A1 (ja) * 2021-03-31 2022-10-06 デンカ株式会社 半硬化物複合体の製造方法、硬化物複合体の製造方法、及び半硬化物複合体

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