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WO2011111667A1 - Composition durcissable, produit durci, et procédé de mise en œuvre de composition durcissable - Google Patents

Composition durcissable, produit durci, et procédé de mise en œuvre de composition durcissable Download PDF

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Publication number
WO2011111667A1
WO2011111667A1 PCT/JP2011/055273 JP2011055273W WO2011111667A1 WO 2011111667 A1 WO2011111667 A1 WO 2011111667A1 JP 2011055273 W JP2011055273 W JP 2011055273W WO 2011111667 A1 WO2011111667 A1 WO 2011111667A1
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Prior art keywords
group
curable composition
silane compound
optical element
silane
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PCT/JP2011/055273
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English (en)
Japanese (ja)
Inventor
幹広 樫尾
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リンテック株式会社
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Priority to CN201180012898.9A priority Critical patent/CN102906198B/zh
Priority to KR1020127023138A priority patent/KR101768246B1/ko
Priority to JP2012504454A priority patent/JP5725479B2/ja
Publication of WO2011111667A1 publication Critical patent/WO2011111667A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • 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
    • C08G59/40—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
    • C08G59/4215—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof cycloaliphatic
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C08L63/06—Triglycidylisocyanurates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H01L23/293—Organic, e.g. plastic
    • H01L23/296—Organo-silicon compounds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/0001—Technical content checked by a classifier
    • H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/095—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00 with a principal constituent of the material being a combination of two or more materials provided in the groups H01L2924/013 - H01L2924/0715
    • H01L2924/097—Glass-ceramics, e.g. devitrified glass
    • H01L2924/09701—Low temperature co-fired ceramic [LTCC]

Definitions

  • the present invention relates to a curable composition from which a cured product having excellent transparency and heat resistance and high adhesive strength can be obtained, a cured product obtained by curing the composition, and the composition as an optical element fixing material.
  • the present invention relates to a method for use as an adhesive for optical devices or a sealant for optical element fixing materials.
  • curable compositions have been improved in various ways depending on the application, and have been widely used in industry as raw materials for optical parts and molded articles, adhesives, coating agents, and the like.
  • a curable composition that forms a cured product having excellent transparency is used as a raw material for optical components and a coating agent thereof, and a curable composition that forms a cured product having a high adhesive force is used as an adhesive or coating.
  • curable compositions have also been used as compositions for optical element fixing materials, such as adhesives for optical element fixing materials and sealing agents for optical element fixing materials, when producing optical element sealing bodies. It is coming.
  • the optical element examples include various lasers such as a semiconductor laser (LD), light emitting elements such as a light emitting diode (LED), a light receiving element, a composite optical element, and an optical integrated circuit.
  • LD semiconductor laser
  • LED light emitting diode
  • a composite optical element a composite optical element
  • optical integrated circuit an optical integrated circuit
  • the cured product of the composition for optical element fixing materials is exposed to higher energy light and higher temperature heat generated from the optical element for a long time, and deteriorates and cracks. The problem of generating or peeling occurred.
  • Patent Documents 1 to 3 propose compositions for optical element fixing materials containing a polysilsesquioxane compound as a main component.
  • a cured product of a composition for optical element fixing materials mainly composed of a polysilsesquioxane compound described in Patent Documents 1 to 3 heat resistance and transparency can be maintained while maintaining sufficient adhesive force. It was sometimes difficult to get.
  • Patent Document 4 proposes an epoxy resin composition using an alicyclic epoxy resin
  • Patent Document 5 proposes an epoxy resin composition containing a polythiol compound. ing.
  • these compositions are used, there is a case where sufficient light deterioration resistance accompanying a change with time cannot be satisfied or the adhesive force is lowered.
  • JP 2004-359933 A JP 2005-263869 A JP 2006-328231 A Japanese Patent Laid-Open No. 7-309927 JP 2009-001752 A
  • the present invention has been made in view of the actual situation of the prior art, and is a curable composition that is excellent in heat resistance and transparency and that can provide a cured product having high adhesive strength. It is an object of the present invention to provide a cured product and a method for using the composition as an adhesive for optical element fixing materials or an encapsulant for optical element fixing materials.
  • the present inventors have (A) a specific silane compound copolymer, (B) an epoxy compound having an isocyanurate skeleton, and (C) an alicyclic group having a carboxyl group.
  • the cured product of the composition containing the acid anhydride-containing curing agent and (D) the silane coupling agent having an acid anhydride structure has excellent transparency and heat resistance over a long period of time, and at a high temperature.
  • the present invention has been completed.
  • the following curable compositions [1] to [9] are provided. [1] (A) In the molecule, the following formulas (i), (ii) and (iii)
  • R 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • X 0 represents a halogen atom, a cyano group or a group represented by the formula: OG (wherein G represents a protecting group for a hydroxyl group) D) represents a single bond or a linking group.
  • R 2 represents an alkyl group having 1 to 20 carbon atoms or an optionally substituted phenyl group.
  • the content ratio of the components (A), (B), (C), and (D) is a mass ratio of (A) and [(B) + (C) + (D)].
  • the curable composition according to [1] or [2], wherein [(B) + (C) + (D)] 90:10 to 50:50.
  • R 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • X 0 represents a halogen atom, a cyano group or a group represented by the formula: OG (wherein G represents a protecting group for a hydroxyl group) D) represents a single bond or a linking group.
  • R 3 represents an alkyl group having 1 to 6 carbon atoms
  • X 1 represents a halogen atom
  • p represents an integer of 0 to 3.
  • Q represents an integer of 0 to 3.
  • the curing agent (C) is composed of one or more selected from alicyclic acid anhydrides having a carboxyl group and other alicyclic acid anhydrides, and the mass ratio thereof is (carboxyl group
  • the curable composition according to [1] or [4], wherein: (an alicyclic acid anhydride): (other alicyclic acid anhydride) 100: 0 to 10:90.
  • the curable composition according to [1] or [4] which is a composition for an optical element fixing material.
  • the following [10] and [11] cured products are provided.
  • [10] A cured product obtained by curing the curable composition according to [1] or [4].
  • [11] The cured product according to [10], which is an optical element fixing material.
  • [12] A method of using the curable composition according to [1] or [4] as an adhesive for an optical element fixing material.
  • [13] A method of using the curable composition according to [1] or [4] as a sealant for an optical element fixing material.
  • the curable composition of the present invention even when irradiated with high energy light or in a high temperature state, it does not color and does not deteriorate transparency, and has excellent transparency over a long period of time. In addition, a cured product having a high adhesive force even at a high temperature can be obtained.
  • the curable composition of the present invention can be used when forming an optical element fixing material, and particularly preferably used as an adhesive for an optical element fixing material and an encapsulant for an optical element fixing material. it can.
  • Curable composition of the present invention comprises: (A) In the molecule, the following formulas (i), (ii) and (iii)
  • R 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • X 0 represents a halogen atom, a cyano group or a group represented by the formula: OG (wherein G represents a protecting group for a hydroxyl group) D) represents a single bond or a linking group.
  • R 2 represents an alkyl group having 1 to 20 carbon atoms or an optionally substituted phenyl group.
  • the curable composition of the present invention comprises (i) and (i) of the repeating units represented by the formulas (i), (ii) and (iii) as the component (A). having a repeating unit of ii), (i) and (iii), (ii) and (iii), or (i), (ii) and (iii), and having a weight average molecular weight of 1,000 to 30,000 A silane compound copolymer (hereinafter sometimes referred to as “silane compound copolymer (A)”).
  • the silane compound copolymer (A) may have one type of repeating unit represented by (i), (ii), or (iii), or may have two or more types.
  • R 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, preferably a hydrogen atom.
  • alkyl group having 1 to 6 carbon atoms represented by R 1 include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, t-butyl group, i-butyl group, s- Examples thereof include a butyl group, an n-pentyl group, and an n-hexyl group.
  • X 0 represents a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; a cyano group; or a group represented by the formula: OG.
  • G represents a protecting group for a hydroxyl group.
  • the well-known protecting group known as a hydroxyl-protecting group is mentioned.
  • acyl protecting groups silyl protecting groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, t-butyldiphenylsilyl group; methoxymethyl group, methoxyethoxymethyl group, 1-ethoxyethyl group
  • An acetal type protective group such as tetrahydropyran-2-yl group or tetrahydrofuran-2-yl group; an alkoxycarbonyl type protective group such as t-butoxycarbonyl group; methyl group, ethyl group, t-butyl group, octyl group
  • ether-based protecting groups such as allyl group, triphenylmethyl group, benzyl group, p-
  • the acyl-based protecting group is specifically a group represented by the formula: —C ( ⁇ O) R 5 .
  • R 5 represents carbon such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, and n-pentyl group.
  • Examples of the substituent of the phenyl group which may have a substituent represented by R 5 include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i -Alkyl groups such as butyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl and i-octyl; halogen atoms such as fluorine, chlorine and bromine An alkoxy group such as a methoxy group or an ethoxy group;
  • a chlorine atom a group represented by the formula: OG ′ (wherein G ′ is an acyl group) And a group selected from a cyano group, a group selected from a chlorine atom, an acetoxy group and a cyano group is more preferable, and an acetoxy group is particularly preferable.
  • D represents a single bond or a linking group.
  • the linking group include a divalent organic group that may have a substituent.
  • the organic group preferably has 1 to 20 carbon atoms, and more preferably 1 to 10 carbon atoms.
  • Examples of the divalent organic group that may have a substituent include an alkylene group that may have a substituent, an alkenylene group that may have a substituent, and a substituent.
  • alkynylene group which may have a substituent an alkynylene group which may have a substituent, an arylene group which may have a substituent, an arylene group which may have a substituent (an alkylene group, an alkenylene group or an alkynylene group) and an arylene group which may have a substituent; And a divalent group consisting of the above-mentioned combinations.
  • alkylene group of the alkylene group which may have a substituent a methylene group, an ethylene group, a propylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, etc., having 1 to 20 carbon atoms, preferably And an alkylene group having 1 to 10 carbon atoms.
  • the alkenylene group of the alkenylene group which may have a substituent is an alkenylene group having 2 to 20 carbon atoms such as vinylene group, propenylene group, butenylene group or pentenylene group, preferably an alkenylene group having 2 to 10 carbon atoms. Is mentioned.
  • alkynylene group which may have a substituent examples include alkynylene groups having 2 to 20 carbon atoms such as ethynylene group and propynylene group, preferably alkynylene groups having 2 to 10 carbon atoms.
  • the arylene group of the arylene group which may have a substituent is preferably an arylene group having 6 to 20 carbon atoms such as an o-phenylene group, an m-phenylene group, a p-phenylene group, or a 2,6-naphthylene group, Includes an arylene group having 6 to 10 carbon atoms.
  • Examples of the substituent for the alkylene group, alkenylene group, and alkynylene group include a halogen atom such as a fluorine atom and a chlorine atom; an alkoxy group such as a methoxy group and an ethoxy group; an alkylthio group such as a methylthio group and an ethylthio group; a methoxycarbonyl group; An alkoxycarbonyl group such as an ethoxycarbonyl group; and the like.
  • substituents for the arylene group include: a cyano group; a nitro group; a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom; an alkyl group such as a methyl group and an ethyl group; an alkoxy group such as a methoxy group and an ethoxy group; And alkylthio groups such as ethylthio group; and the like.
  • substituents may be bonded at arbitrary positions in groups such as an alkylene group, an alkenylene group, an alkynylene group, and an arylene group, and a plurality of them may be bonded in the same or different manner.
  • the divalent group consisting of a combination of an optionally substituted (alkylene group, alkenylene group, or alkynylene group) and an optionally substituted arylene group has the above substituents.
  • a group in which at least one kind of (alkylene group, alkenylene group, or alkynylene group) which may be present and at least one kind of arylene group which may have the substituent are bonded in series. Specific examples include groups represented by the following formula.
  • D is preferably an alkylene group having 1 to 10 carbon atoms, more preferably an alkylene group having 1 to 6 carbon atoms, and a methylene group or an ethylene group is preferable because a cured product having high adhesive strength can be obtained. Particularly preferred.
  • R 2 represents an alkyl group having 1 to 20 carbon atoms or an optionally substituted phenyl group.
  • alkyl group having 1 to 20 carbon atoms represented by R 2 include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t- Examples include a butyl group, n-pentyl group, n-hexyl group, n-octyl group, i-octyl group, n-nonyl group, n-decyl group, n-dodecyl group and the like.
  • Examples of the substituent of the phenyl group which may have a substituent represented by R 2 include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i -Alkyl groups such as butyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl and i-octyl; alkoxy groups such as methoxy and ethoxy; fluorine atoms And halogen atoms such as chlorine atom.
  • curing material which is excellent in transparency and adhesiveness, and excellent in heat resistance is obtained.
  • the amount of the group represented by the formula: R 1 —CH (X 0 ) —D— and R 2 can be quantified by, for example, measuring the NMR spectrum of the silane compound copolymer (A).
  • the silane compound copolymer (A) may be any copolymer such as a random copolymer, a block copolymer, a graft copolymer, and an alternating copolymer, but a random copolymer is particularly preferable. .
  • the weight average molecular weight (Mw) of the silane compound copolymer (A) is in the range of 1,000 to 30,000, preferably in the range of 1,500 to 6,000. By being in the said range, the hardened
  • a weight average molecular weight (Mw) can be calculated
  • the molecular weight distribution (Mw / Mn) of the silane compound copolymer (A) is not particularly limited, but is usually in the range of 1.0 to 3.0, preferably 1.1 to 2.0. By being in the said range, the hardened
  • the silane compound copolymer (A) can be used alone or in combination of two or more.
  • the silane compound copolymer (A) is a polysilsesquioxane compound having a ladder structure.
  • the fact that the silane compound copolymer has a ladder structure can be confirmed, for example, by performing infrared absorption spectrum measurement, X-ray diffraction measurement, and NMR measurement of the reaction product.
  • the component (A) is (A ′) Formula (1): R 1 —CH (X 0 ) —D—Si (OR 3 ) p (X 1 ) 3-p [Wherein R 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, X 0 represents a halogen atom, a cyano group or a group represented by the formula: OG (wherein G represents a protecting group for a hydroxyl group) D) represents a single bond or a linking group. R 3 represents an alkyl group having 1 to 6 carbon atoms, X 1 represents a halogen atom, and p represents an integer of 0 to 3.
  • silane compound copolymer having a weight average molecular weight of 1,000 to 30,000 (hereinafter referred to as “silane compound copolymer”) obtained by condensing a mixture of silane compounds containing at least one silane compound (2) represented by Polymer (A ′) ”), and the silane compound copolymer (A) is preferably a silane compound copolymer (A ′).
  • the silane compound (1) is a compound represented by the formula (1): R 1 —CH (X 0 ) —D—Si (OR 3 ) p (X 1 ) 3-p .
  • R 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, preferably a hydrogen atom. Specific examples include those exemplified as R 1 in the silane compound copolymer (A).
  • X 0 is a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, a cyano group, or a group represented by the formula: OG (wherein, G represents a protecting group for a hydroxyl group).
  • D represents a single bond or a linking group. Specific examples of those represented by X 0 and D, respectively, those exemplified as X 0 and D in the silane compound copolymer (A).
  • R 3 is methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc.
  • X 1 represents a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
  • p represents an integer of 0 to 3. When p is 2 or more, the ORs 3 may be the same or different. When (3-p) is 2 or more, X 1 may be the same or different.
  • silane compound (1) examples include chloromethyltrimethoxysilane, bromomethyltriethoxysilane, 2-chloroethyltripropoxysilane, 2-bromoethyltributoxysilane, 3-chloropropyltrimethoxysilane, 3-chloro Propyltriethoxysilane, 3-chloropropyltripropoxysilane, 3-chloropropyltributoxysilane, 3-bromopropyltrimethoxysilane, 3-bromopropyltriethoxysilane, 3-bromopropyltripropoxysilane, 3-bromopropyltri Butoxysilane, 3-fluoropropyltrimethoxysilane, 3-fluoropropyltriethoxysilane, 3-fluoropropyltripropoxysilane, 3-fluoropropyltributoxysilane, 3-iodopropylto Methoxysilane, 2-chlor
  • trialkoxysilane compounds in which X 0 is a halogen atom, trialkoxysilane in which X 0 is a cyano group Compounds, or trialkoxysilane compounds in which X 0 is a group represented by the formula: OG are preferred, trialkoxysilane compounds having a 3-chloropropyl group, trialkoxysilane compounds having a 3-acetoxypropyl group More preferred are trialkoxysilane compounds having a 2-cyanoethyl group or trialkoxysilane compounds having a 3-cyanopropyl group.
  • the silane compound (2) is a compound represented by the formula (2): R 2 Si (OR 4 ) q (X 2 ) 3-q .
  • R 2 represents an alkyl group having 1 to 20 carbon atoms or a phenyl group which may have a substituent. Specific examples include those exemplified as R 2 in the silane compound copolymer (A).
  • R 4 represents the same alkyl group having 1 to 6 carbon atoms as R 3 .
  • X 2 represents the same halogen atom as X 1 .
  • q represents an integer of 0 to 3. When q is 2 or more, OR 4 may be the same or different. When (3-q) is 2 or more, X 2 may be the same or different.
  • silane compound (2) examples include methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, n-propyltrimethoxysilane, n-butyltriethoxysilane, i-butyltrimethoxy.
  • Alkyltrialkoxysilane compounds such as silane, n-pentyltriethoxysilane, n-hexyltrimethoxysilane, i-octyltriethoxysilane, dodecyltrimethoxysilane, methyldimethoxyethoxysilane, methyldiethoxymethoxysilane;
  • Alkylhalogenoalkoxysilane compounds such as methylchlorodimethoxysilane, methyldichloromethoxysilane, methylchlorodiethoxysilane, ethylchlorodimethoxysilane, ethyldichloromethoxysilane, n-propylchlorodimethoxysilane, n-propyldichloromethoxysilane;
  • Alkyltrihalogenosilane compounds such as methyltrichlorosilane, methyltribromosilane, eth
  • phenyltrimethoxysilane 4-methoxyphenyltrimethoxysilane, 2-chlorophenyltrimethoxysilane, phenyltriethoxysilane, 2-methoxyphenyltriethoxysilane, phenyldimethoxyethoxysilane, phenyldiethoxymethoxysilane
  • phenyltrialkoxysilane compounds Phenylhalogenoalkoxysilane compounds which may have a substituent such as phenylchlorodimethoxysilane, phenyldichloromethoxysilane, phenylchloromethoxyethoxysilane, phenylchlorodiethoxysilane, phenyldichloroethoxysilane
  • phenyltrihalogenosilane compounds which may have a substituent such as phenyltrichlorosilane, phenyltribro
  • the method for condensing the mixture of the silane compounds is not particularly limited, but the silane compound (1), the silane compound (2), and other silane compounds as required are dissolved in a solvent, and a predetermined amount of catalyst is added. And a method of stirring at a predetermined temperature.
  • the catalyst used may be either an acid catalyst or a base catalyst.
  • the acid catalyst include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid; organic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, acetic acid and trifluoroacetic acid; Can be mentioned.
  • Base catalysts include trimethylamine, triethylamine, lithium diisopropylamide, lithium bis (trimethylsilyl) amide, pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene, aniline, picoline, 1,4-diazabicyclo [2 2.2]
  • Organic bases such as octane and imidazole;
  • Organic salt hydroxides such as tetramethylammonium hydroxide and tetraethylammonium hydroxide;
  • Metals such as sodium methoxide, sodium ethoxide, sodium t-butoxide, and potassium t-butoxide Alcoholates;
  • Metal hydrides such as sodium hydride and calcium hydride;
  • Metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide;
  • Metal carbonates such as sodium carbonate, potassium carbonate and magnesium carbonate; Carbonated water And the like are; sodium, metal hydrogen carbonates such as potassium hydrogen carbon
  • an acid catalyst is preferable, and an inorganic acid is more preferable.
  • the amount of catalyst used is usually in the range of 0.1 mol% to 10 mol%, preferably 1 mol% to 5 mol%, based on the total molar amount of the silane compound.
  • the solvent to be used can be appropriately selected according to the type of the silane compound.
  • water aromatic hydrocarbons such as benzene, toluene and xylene; esters such as methyl acetate, ethyl acetate, propyl acetate and methyl propionate; ketones such as acetone, methyl ethyl ketone, methyl i-butyl ketone and cyclohexanone; methyl And alcohols such as alcohol, ethyl alcohol, n-propyl alcohol, i-propyl alcohol, n-butyl alcohol, i-butyl alcohol, s-butyl alcohol and t-butyl alcohol.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • esters such as methyl acetate, ethyl acetate, propyl acetate and methyl propionate
  • ketones such as acetone, methyl ethyl ket
  • water, aromatic hydrocarbons, and a mixed solvent thereof are preferable, and a mixed solvent of water and toluene is particularly preferable.
  • the ratio of water to toluene (volume ratio) is preferably 1: 9 to 9: 1, more preferably 7: 3 to 3: 7.
  • the amount of the solvent used is such that the total molar amount of the silane compound per liter of solvent is usually 0.1 mol to 10 mol, preferably 0.5 mol to 10 mol.
  • the temperature at which the silane compound is condensed (reacted) is usually in the temperature range from 0 ° C. to the boiling point of the solvent used, preferably in the range of 20 ° C. to 100 ° C. If the reaction temperature is too low, the progress of the condensation reaction may be insufficient. On the other hand, if the reaction temperature is too high, it is difficult to suppress gelation. The reaction is usually completed in 30 minutes to 20 hours.
  • an acid catalyst After completion of the reaction, when an acid catalyst is used, an alkaline aqueous solution such as an aqueous sodium hydrogen carbonate solution is added to the reaction solution. When a basic catalyst is used, an acid such as hydrochloric acid is added to the reaction solution. Neutralization is performed, and the salt generated at that time is removed by filtration or washing with water, etc., and the desired silane compound copolymer can be obtained.
  • the curable composition of the present invention contains an epoxy compound having an isocyanurate skeleton (hereinafter sometimes referred to as “epoxy compound (B)”) as the component (B). To do. Since the curable composition of the present invention contains the epoxy compound (B), a cured product having excellent heat resistance and transparency can be obtained even after heat history.
  • epoxy compound (B) an epoxy compound having an isocyanurate skeleton
  • the epoxy compound (B) is not particularly limited as long as it is a compound having an isocyanurate skeleton (the following (c), in the formula,-represents a bond) and an epoxy ring in the molecule.
  • the isocyanurate skeleton (c) may have a tautomer as shown below (cyanurate skeleton (c ′), wherein — represents a bond), and an epoxy having this skeleton is present.
  • the compound is also included in the epoxy compound (B) used in the present invention.
  • epoxy compound (B) as shown in the following formulas (c-1) to (c-3), at least one of hydrogen atoms bonded to the nitrogen atoms at the 1, 3, and 5 positions of the isocyanurate ring is used.
  • a compound in which one is substituted with a group (E) having an epoxy ring is preferred.
  • E represents a group having an epoxy ring
  • R represents an arbitrary group other than a group having an epoxy ring such as a hydrogen atom or an organic group.
  • group (E) having an epoxy ring for example, the following formula
  • a, b and c each represents an integer of 1 to 20, and the methylene group may be substituted with an alkyl group such as a methyl group or an ethyl group).
  • epoxy compound (B) examples include glycidyl isocyanurate, diglycidyl isocyanurate, tris (2,3-epoxypropyl) isocyanurate, tris (glycidoxy) from the viewpoint of obtaining a cured product having high adhesive strength.
  • glycidyl isocyanurate diglycidyl isocyanurate
  • tris (2,3-epoxypropyl) isocyanurate tris (glycidoxy) from the viewpoint of obtaining a cured product having high adhesive strength.
  • Propyl) isocyanurate tris ( ⁇ -methylglycidyl) isocyanurate, and a mixture containing two or more of these compounds.
  • epoxy compound (B) those commercially available as epoxy compounds having an isocyanurate skeleton (for example, trade names: TEPIC-S, TEPIC-PAS B22, trade names: TEPIC-PAS B26, etc. are all Nissan) Chemical Industries, Ltd.) can also be used as it is.
  • the compounding amount of the epoxy compound (B) is not particularly limited, but from the viewpoint of obtaining a cured product having higher adhesive strength, the epoxy equivalent is preferably 50 to 300 g / eq, particularly preferably 100 to 200 g / eq.
  • the epoxy equivalent is a value measured according to JIS K7236: 2001.
  • curable composition of the present invention may be referred to as a curing agent (hereinafter referred to as “curing agent (C)”) containing an alicyclic acid anhydride having a carboxyl group as the component (C). )including. Since the curable composition of this invention contains a hardening
  • the alicyclic acid anhydride having a carboxyl group is an acid anhydride having an alicyclic structure in which at least one carboxyl group is substituted.
  • Examples of the alicyclic structure include a saturated cyclic hydrocarbon (cycloalkane) structure and an unsaturated cyclic hydrocarbon (cycloalkene, cycloalkyne) structure.
  • the alicyclic acid anhydrides include 3-methyl-1,2,3,6-tetrahydrophthalic anhydride, 4-methyl-1,2,3,6-tetrahydrophthalic anhydride, tetrahydrophthalic anhydride, 3- Methyl-hexahydrophthalic anhydride, 4-methyl-hexahydrophthalic anhydride, hexahydrophthalic anhydride, methyl nadic anhydride, 5-norbornene-2,3-dicarboxylic anhydride, norbornane-2,3-dicarboxylic anhydride, Examples include methyl-5-norbornene-2,3-dicarboxylic acid anhydride, methyl-norbornane-2,3-dicarboxylic acid anhydride, and the like.
  • the carboxyl group may be substituted at any position of the alicyclic structure of the alicyclic acid anhydride, and the position of substitution and the number of carboxyl groups to be substituted are not particularly limited.
  • cyclohexane-1,2,4-tricarboxylic acid-1,2 anhydride and cyclohexane-1,2,3-tricarboxylic acid-1,2 anhydride in which a carboxyl group is substituted with hexahydrophthalic anhydride are preferable.
  • Cyclohexane-1,2,4-tricarboxylic acid-1,2 anhydride is particularly preferable. This compound may exist as a stereoisomer, but may be any isomer.
  • the alicyclic acid anhydride having a carboxyl group can be used alone or in combination of two or more.
  • the curing agent (C) may further contain another curing agent.
  • Other curing agents include alicyclic acid anhydrides having no carboxyl group (hereinafter referred to as “other alicyclic acid anhydrides”), polyazeline acid anhydrides and other aliphatic acid anhydrides, aliphatic Examples include amine curing agents, alicyclic amine curing agents, secondary or tertiary amine curing agents, aromatic amine curing agents, dicyandiamide, boron trifluoride amine complex salts, and imidazole compounds.
  • curing agent can be used individually by 1 type or in combination of 2 or more types.
  • other alicyclic acid anhydrides are preferable because cured products having high adhesive force even at high temperatures are obtained.
  • the other alicyclic acid anhydrides include those exemplified as the alicyclic acid anhydride of the alicyclic acid anhydride having a carboxyl group. Of these, 3-methyl-hexahydrophthalic anhydride and 4-methyl-hexahydrophthalic anhydride are preferable, and 4-methyl-hexahydrophthalic anhydride is particularly preferable.
  • curing agent (C) consists of 1 type, or 2 or more types chosen from the alicyclic acid anhydride which has a carboxyl group, and other alicyclic acid anhydrides,
  • the mass ratio is (it has a carboxyl group.
  • Alicyclic acid anhydride): (other alicyclic acid anhydrides) 100: 0 to 10:90 is preferable, and 50:50 to 10:90 is more preferable.
  • the curable composition of the present invention has a silane coupling agent having an acid anhydride structure as the component (D) (hereinafter sometimes referred to as “silane coupling agent (D)”). including. Since the curable composition of this invention contains a silane coupling agent (D), it can obtain the hardened
  • the silane coupling agent (D) is an organosilicon compound having both a group (Y) having an acid anhydride structure and a hydrolyzable group (OR b ) in one molecule. Specifically, it is a compound represented by the following formula (d).
  • Y represents an acid anhydride structure
  • R a represents an alkyl group having 1 to 6 carbon atoms or an optionally substituted phenyl group
  • R b represents an alkyl group having 1 to 6 carbon atoms.
  • I represents an integer of 1 to 3
  • j represents an integer of 0 to 2
  • k represents an integer of 1 to 3
  • i + j + k 4.
  • the alkyl group having 1 to 6 carbon atoms represented by R a and R b is the same as that exemplified above as the alkyl group having 1 to 6 carbon atoms represented by R 1 .
  • the phenyl group which may have a substituent represented by R a is exemplified above as the phenyl group which may have a substituent represented by R 2 .
  • the same group is mentioned.
  • the compound represented by the formula (d) the following formula (d-1)
  • R b , h, i, j and k represent the same meaning as described above.
  • the compound represented by these is preferable.
  • h is preferably 2 to 8.
  • silane coupling agent represented by the formula (d-1) examples include 2-trimethoxysilylethyl succinic anhydride and 3-triethoxysilylpropyl succinic anhydride.
  • a silane coupling agent (D) can be used individually by 1 type or in combination of 2 or more types.
  • the content ratio of the components (A), (B), (C) and (D) is (A) and [(B) + (C) + (D)].
  • each component in such a ratio it is possible to obtain a curable composition capable of obtaining a cured product having excellent transparency and heat resistance over a long period of time and having a high adhesive force even at high temperatures.
  • the curable composition of the present invention may further contain other components as long as the object of the present invention is not impaired.
  • other components include a curing catalyst, an antioxidant, an ultraviolet absorber, a light stabilizer, and a diluent.
  • a curing catalyst is added to accelerate curing.
  • the curing catalyst include 2-methylimidazole and triphenylphosphine. These curing catalysts can be used alone or in combination of two or more.
  • An antioxidant is added to prevent oxidative degradation during heating.
  • examples of the antioxidant include phosphorus antioxidants, phenolic antioxidants, sulfur antioxidants and the like.
  • Phosphorous antioxidants include triphenyl phosphite, diphenylisodecyl phosphite, phenyl diisodecyl phosphite, tris (nonylphenyl) phosphite, diisodecylpentaerythritol phosphite, tris (2,4-di-t-butylphenyl) ) Phosphite, cyclic neopentanetetrayl bis (octadecyl) phosphite, cyclic neopentanetetrayl bis (2,4-di-t-butylphenyl) phosphite, cyclic neopentanetetrayl bis (2,4 -Phosphites such as -di-t-butyl-4-methylphenyl) phosphite, bis [2-tert-butyl-6-methyl-4-
  • phenolic antioxidants examples include 2,6-di-t-butyl-p-cresol, dibutylhydroxytoluene, butylated hydroxyanisole, 2,6-di-t-butyl-p-ethylphenol, stearyl- ⁇ - Monophenols such as (3,5-di-t-butyl-4-hydroxyphenyl) propionate; 2,2′-methylenebis (4-methyl-6-t-butylphenol), 2,2′-methylenebis (4- Ethyl-6-tert-butylphenol), 4,4′-thiobis (3-methyl-6-tert-butylphenol), 4,4′-butylidenebis (3-methyl-6-tert-butylphenol), 3,9-bis [1,1-dimethyl-2- ⁇ - (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy ⁇ ethyl] 2,4,8 Bisphenols such as 1,10-tetraoxaspiro [5,5]
  • sulfur-based antioxidants examples include dilauryl-3,3'-thiodipropionate, dimyristyl-3,3'-thiodipropionate, distearyl-3,3'-thiodipropionate, and the like.
  • antioxidants can be used alone or in combination of two or more.
  • the curable composition of the present invention contains the component (B) and the component (D)
  • oxidative deterioration during heating hardly occurs even without an antioxidant.
  • the amount used is usually 0.01 to 10 parts by mass with respect to 100 parts by mass of the silane compound copolymer (A) or (A ′).
  • the ultraviolet absorber is added for the purpose of improving the light resistance of the resulting cured product.
  • the ultraviolet absorber include salicylic acids such as phenyl salicylate, pt-butylphenyl salicylate, p-octylphenyl salicylate; 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4 -Octoxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2-hydroxy-4-methoxy- Benzophenones such as 5-sulfobenzophenone; 2- (2′-hydroxy-5′-methylphenyl) benzotriazole, 2- (2′-hydroxy-5′-t-butylphenyl) benzotriazole, 2- (2 ′ -Hydroxy-3 ', 5'-di-t
  • ultraviolet absorbers can be used alone or in combination of two or more.
  • the amount of the ultraviolet absorber used is usually 0.01 to 10 parts by mass with respect to 100 parts by mass of the silane compound copolymer (A) or (A ′).
  • the light stabilizer is added for the purpose of improving the light resistance of the resulting cured product.
  • the light stabilizer include poly [ ⁇ 6- (1,1,3,3, -tetramethylbutyl) amino-1,3,5-triazine-2,4-diyl ⁇ ⁇ (2,2,6 , 6-tetramethyl-4-piperidine) imino ⁇ hexamethylene ⁇ (2,2,6,6-tetramethyl-4-piperidine) imino ⁇ ] and the like.
  • light stabilizers can be used alone or in combination of two or more.
  • the amount of the light stabilizer used is usually 0.01 to 10 parts by mass with respect to 100 parts by mass of the silane compound copolymer (A) or (A ′).
  • a diluent is added in order to adjust the viscosity of the curable composition.
  • the diluent include glycerin diglycidyl ether, butanediol diglycidyl ether, diglycidyl aniline, neopentyl glycol glycidyl ether, cyclohexane dimethanol diglycidyl ether, alkylene diglycidyl ether, polyglycol diglycidyl ether, and polypropylene glycol diglycidyl ether.
  • Examples include ether, trimethylolpropane triglycidyl ether, glycerin triglycidyl ether, 4-vinylcyclohexene monooxide, vinylcyclohexene dioxide, methylated vinylcyclohexene dioxide, and the like. These diluents can be used alone or in combination of two or more.
  • the curable composition of the present invention is, for example, known by blending the above-mentioned components (A) or (A ′), (B), (C), (D), and other components as required in a predetermined ratio. It can be obtained by mixing and defoaming by a method.
  • the curable composition of the present invention obtained as described above, even when irradiated with high energy light or in a high temperature state, it is not colored and the transparency is not lowered, and it is long-term. It is possible to obtain a cured product having excellent transparency and high adhesive strength. Therefore, the curable composition of the present invention is suitably used as a raw material for optical parts and molded articles, an adhesive, a coating agent, and the like. In particular, since the problem relating to deterioration of the optical element fixing material accompanying the increase in luminance of the optical element can be solved, the curable composition of the present invention can be suitably used as a composition for optical element fixing material. it can.
  • the second of the present invention is a cured product obtained by curing the curable composition of the present invention.
  • Heat curing is mentioned as a method of hardening the curable composition of this invention.
  • the heating temperature for curing is usually 100 to 200 ° C., and the heating time is usually 10 minutes to 20 hours, preferably 30 minutes to 10 hours.
  • the cured product of the present invention has excellent transparency over a long period of time, even when irradiated with high energy light or in a high temperature state, without being colored and having a reduced transparency, and High adhesive strength. Therefore, the hardened
  • the cured product of the present invention has a high adhesive force, for example, by measuring the adhesive force as follows. That is, the curable composition is applied to the mirror surface of the silicon chip, and the coated surface is placed on the adherend and pressure-bonded, and then heated and cured. This is left for 30 seconds on a measurement stage of a bond tester that has been heated to a predetermined temperature (for example, 23 ° C., 100 ° C.) in advance, and is horizontal (sheared) with respect to the adhesive surface from a position 50 ⁇ m high from the adherend. Direction) and measure the adhesive force between the test piece and the adherend.
  • the adhesive strength of the cured product is preferably 110 N / 2 mm ⁇ or more at 23 ° C.
  • the cured product is excellent in transparency by measuring light transmittance.
  • the light transmittance of the cured product is preferably 80% or more, particularly preferably 84% or more for light having a wavelength of 400 nm, and preferably 87% or more for light having a wavelength of 450 nm.
  • the cured product is excellent in heat resistance over a long period of time because the change in transparency is small even after the cured product is placed at a high temperature for a long time.
  • the transmittance at a wavelength of 400 nm is preferably 70% or more of the initial transmittance, more preferably 80% or more.
  • the third of the present invention is a method of using the curable composition of the present invention as an adhesive for optical element fixing materials or an encapsulant for optical element fixing materials.
  • optical elements include light emitting elements such as LEDs and LDs, light receiving elements, composite optical elements, and optical integrated circuits.
  • the curable composition of this invention can be used conveniently as an adhesive agent for optical element fixing materials.
  • the composition is applied to one or both adhesive surfaces of a material to be bonded (such as an optical element and its substrate). After the pressure bonding, there is a method in which the material to be bonded is firmly bonded by heat curing.
  • Main substrate materials for bonding optical elements include glass such as soda lime glass and heat-resistant hard glass; ceramics; iron, copper, aluminum, gold, silver, platinum, chromium, titanium, and alloys of these metals , Metals such as stainless steel (SUS302, SUS304, SUS304L, SUS309, etc.); polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, ethylene-vinyl acetate copolymer, polystyrene, polycarbonate, polymethylpentene, polysulfone, polyetheretherketone , Synthetic resins such as polyethersulfone, polyphenylene sulfide, polyetherimide, polyimide, polyamide, acrylic resin, norbornene resin, cycloolefin resin, glass epoxy resin, etc. .
  • the heating temperature at the time of heat curing is usually 100 to 200 ° C. although it depends on the curable composition used.
  • the heating time is usually 10 minutes to 20 hours, preferably 30 minutes to 10 hours.
  • the curable composition of this invention can be used suitably as a sealing agent of an optical element sealing body.
  • the curable composition of the present invention As a method of using the curable composition of the present invention as a sealant for an optical element fixing material, for example, after molding the composition into a desired shape to obtain a molded body containing the optical element, the process itself And the like, and the like.
  • the method for molding the curable composition of the present invention into a desired shape is not particularly limited, and a known molding method such as a normal transfer molding method or a casting method can be employed.
  • the heating temperature at the time of heat curing is usually 100 to 200 ° C. although it depends on the curable composition used.
  • the heating time is usually 10 minutes to 20 hours, preferably 30 minutes to 10 hours.
  • the obtained optical element sealing body uses the curable composition of the present invention, an optical element having a short peak wavelength of 400 to 490 nm such as white or blue light emitting LED is used. However, it is excellent in transparency and heat resistance that does not deteriorate due to heat or light.
  • the weight average molecular weight (Mw) of the silane compound copolymer obtained in the production example was a standard polystyrene equivalent value, and was measured using the following apparatus and conditions.
  • the obtained precipitate was dissolved and recovered in methyl ethyl ketone, and the solvent was distilled off under reduced pressure with an evaporator, followed by vacuum drying to obtain 14.7 g of a silane compound copolymer (A1).
  • the weight average molecular weight (Mw) of the silane compound copolymer (A1) was 2,700, and the molecular weight distribution (Mw / Mn) was 1.53.
  • IR spectrum (Fourier transform infrared spectrophotometer (FT-IR)) data of the silane compound copolymer (A1) is shown below. Si—Ph: 699 cm ⁇ 1 , 741 cm ⁇ 1 , Si—O: 1132 cm ⁇ 1 , —CO: 1738 cm ⁇ 1
  • the weight average molecular weight (Mw) of the silane compound copolymer (A4) was 2,800, and the molecular weight distribution (Mw / Mn) was 1.56. Further, IR spectrum (Fourier transform infrared spectrophotometer (FT-IR)) data of the silane compound copolymer (A4) is shown below. Si-Ph: 700cm -1, 742cm -1, Si-O: 1132cm -1, epoxy group: 1254cm -1
  • the weight average molecular weight (Mw) of the silane compound copolymer (A5) was 3,000, and the molecular weight distribution (Mw / Mn) was 1.59.
  • IR spectrum data of the silane compound copolymer (A5) is shown below.
  • the weight average molecular weight (Mw) of the silane compound copolymer (A6) was 3,300, and the molecular weight distribution (Mw / Mn) was 1.59.
  • IR spectrum data of the silane compound copolymer (A6) is shown below. Si-Ph: 700cm -1, 742cm -1, Si-O: 1133cm -1, -Cl: 648cm -1
  • the weight average molecular weight (Mw) of the silane compound copolymer (A7) was 3,400, and the molecular weight distribution (Mw / Mn) was 1.61.
  • IR spectrum data of the silane compound copolymer (A7) is shown below. Si—Ph: 699 cm ⁇ 1 , 741 cm ⁇ 1 , Si—O: 1132 cm ⁇ 1 , —Cl: 648 cm ⁇ 1
  • Production Example 8 In Production Example 5, the same procedure as in Production Example 5 was conducted, except that the amount of phenyltrimethoxysilane used was 11.9 g (60 mmol) and the amount of 3-chloropropyltrimethoxysilane used was 11.9 g (60 mmol). 12.9 g of silane compound copolymer (A8) was obtained.
  • the weight average molecular weight (Mw) of the silane compound copolymer (A8) was 3,600, and the molecular weight distribution (Mw / Mn) was 1.63.
  • IR spectrum data of the silane compound copolymer (A8) is shown below. Si-Ph: 700cm -1, 741cm -1, Si-O: 1133cm -1, -Cl: 648cm -1
  • the weight average molecular weight (Mw) of the silane compound copolymer (A9) was 2,900, and the molecular weight distribution (Mw / Mn) was 1.58.
  • IR spectrum data of the silane compound copolymer (A9) is shown below. Si-Ph: 700cm -1, 741cm -1, Si-O: 1131cm -1, -CN: 2252cm -1
  • the weight average molecular weight (Mw) of the silane compound copolymer (A10) was 3,200, and the molecular weight distribution (Mw / Mn) was 1.64.
  • IR spectrum data of the silane compound copolymer (A10) is shown below. Si—Ph: 699 cm ⁇ 1 , 742 cm ⁇ 1 , Si—O: 1131 cm ⁇ 1 , —CN: 2253 cm ⁇ 1
  • the weight average molecular weight (Mw) of the silane compound copolymer (A11) was 3,300, and the molecular weight distribution (Mw / Mn) was 1.62.
  • IR spectrum data of the silane compound copolymer (A11) is shown below. Si—Ph: 699 cm ⁇ 1 , 742 cm ⁇ 1 , Si—O: 1131 cm ⁇ 1 , —CN: 2253 cm ⁇ 1
  • the weight average molecular weight (Mw) of the silane compound copolymer (A12) was 3,500, and the molecular weight distribution (Mw / Mn) was 1.61.
  • IR spectrum data of the silane compound copolymer (A12) is shown below. Si-Ph: 700cm -1, 742cm -1, Si-O: 1133cm -1, -CN: 2252cm -1
  • Example 1 10 g of the silane compound copolymer (A1) obtained in Production Example 1 was added to an epoxy compound having an isocyanurate skeleton as an epoxy compound (B) (TEPIC-PAS B26, Nissan Chemical Industries, Ltd., epoxy equivalent 137 g / eq) (the following In Table 1 and Table 1-2, it is described as “B1”.) 1.5 g, 4-methylcyclohexane-1,2-dicarboxylic acid anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) as the curing agent (C) (Described as “C1” in Tables 1 and 1 below) 0.375 g and cyclohexane-1,2,4-tricarboxylic acid-1,2-anhydride (Mitsubishi Gas Chemical Co., Ltd.) ) (An alicyclic acid anhydride having a carboxyl group) (described as “C2” in Table 1 and Table 1 below) 0.75 g, and as a silane coupling agent (D)
  • Example 2 Curable compositions (2) to (7) were obtained in the same manner as in Example 1 using a silane compound copolymer, an epoxy compound, a curing agent, and a silane coupling agent according to Table 1 below.
  • B2 represents an epoxy compound having an isocyanurate skeleton (TEPIC-PAS B22, Nissan Chemical Industries, Ltd., epoxy equivalent 179 g / eq).
  • Curable compositions (8) and (9) were obtained in the same manner as in Example 1 using a silane compound copolymer, an epoxy compound, a curing agent, and a silane coupling agent according to Table 1 below.
  • Example 3 (Comparative Example 3) In Example 1, instead of the epoxy compound (B), 3,4-epoxycyclohexanecarboxylic acid 3,4-epoxycyclohexylmethyl (manufactured by Sigma-Aldrich) (in Table 1 and Table 2 below) It is described as “BF1.”) A curable composition (10) was obtained in the same manner as in Example 1 except that 1.5 g was used.
  • Example 4 (Comparative Example 4) In Example 1, instead of the silane compound copolymer (A1) obtained in Production Example 1, the silane compound copolymer (A4) obtained in Production Example 4 was used. A curable composition (11) was obtained.
  • Example 5 Comparative Example 5
  • silane coupling agent (D1) 3-glycidoxypropyltrimethoxysilane (manufactured by Tokyo Chemical Industry Co., Ltd.) (in Table 1 and Table 2 below, “DF1”)
  • DF1 3-glycidoxypropyltrimethoxysilane
  • Example 8 10 g of the silane compound copolymer (A5) obtained in Production Example 5 and 1.5 g of an epoxy compound having an isocyanurate skeleton as an epoxy compound (B) (TEPIC-PAS B26 manufactured by Nissan Chemical Industries, epoxy equivalent: 137 g / eq)
  • B epoxy compound having an isocyanurate skeleton
  • B epoxy compound having an isocyanurate skeleton
  • C curing agent
  • 0.38 g of 4-methylcyclohexane-1,2-dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) and cyclohexane-1,2,4-tricarboxylic acid-1,2-anhydride (Mitsubishi) By adding 0.75 g of Gas Chemical Co., Ltd.) and 0.38 g of 3-triethoxysilylpropyl succinic anhydride (manufactured by Amax Co.) as the silane coupling agent (D), thoroughly mixing and degassing the whole volume
  • Curable compositions (15) to (31) were obtained in the same manner as in Example 8 using a silane compound copolymer, an epoxy compound, a curing agent, and a silane coupling agent according to Table 1 below.
  • Each of the curable compositions 1 to 31 was applied to a mirror surface of a 2 mm square silicon chip to a thickness of about 2 ⁇ m, and the coated surface was placed on an adherend (silver-plated copper plate) and pressure-bonded. Then, it heat-processed at 180 degreeC for 2 hours, it was made to harden
  • the test piece-attached adherend is left for 30 seconds on a measurement stage of a bond tester (series 4000, manufactured by Daisy) heated in advance to a predetermined temperature (23 ° C., 100 ° C.), and has a height of 50 ⁇ m from the adherend.
  • each of the curable compositions 1 to 31 was poured into a mold so as to have a length of 25 mm, a width of 20 mm, and a thickness of 1 mm, and cured by heating at 140 ° C. for 6 hours to prepare test pieces. With respect to the obtained test piece, the initial transmittance (%) at wavelengths of 400 nm and 450 nm was measured with a spectrophotometer (MPC-3100, manufactured by Shimadzu Corporation).
  • the transmittance at 400 nm was evaluated as “ ⁇ ” when 80% or more, “ ⁇ ” when 70% or more and less than 80%, and “ ⁇ ” when less than 70%.
  • the cured products of the curable compositions of Examples 1 to 15 (1 to 7 and 14 to 21) have a high adhesive strength of 134 N / 2 mm ⁇ or more at 23 ° C. Even at high temperature (100 ° C.), it maintained an adhesive strength of 58% or more of the adhesive strength at 23 ° C., and was excellent in adhesion heat resistance. Moreover, initial transmittance at wavelengths of 400 nm and 450 nm and transmittance after heating were both high, and excellent initial transparency and heat resistance (transparency after heating).
  • the cured products of the curable compositions (8, 12, 13, 22, 25 to 27, 30, 31) of Comparative Examples 1, 5 to 7, 10 to 12, 15, and 16 were inferior in initial transparency.
  • the cured products of the curable compositions (9, 23, 28) of Comparative Examples 2, 8, 13 are inferior in both adhesive strength and adhesive heat resistance, and the curable compositions of Comparative Examples 3, 4, 9, 14 (10, 11). 24, 29) was extremely inferior in heat resistance (transparency after heating).

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Abstract

L'invention concerne une composition durcissable qui comprend : (A) un copolymère de composé silane possédant une unité de répétition spécifique, (B) un composé époxy possédant un squelette d'isocyanurate, (C) un durcisseur qui comprend un anhydride d'acide alicyclique possédant un groupe carboxyle, et (D) un agent adhésif au silane possédant une structure d'anhydride d'acide. En outre, l'invention concerne un produit durci constitué par durcissement de cette composition, et un procédé qui met en œuvre ladite composition en tant qu'adhésif pour matériau de fixation d'élément d'éclairage et en tant que matériau d'étanchéité pour matériau de fixation d'élément d'éclairage. Avec la composition durcissable de l'invention, il est possible d'obtenir un produit durci qui possède d'excellentes propriétés de transparence sur le long terme, sans risque de diminution de ces propriétés de transparence du fait d'une coloration, et qui possède également une force d'adhérence élevée y compris à températures élevées, même dans le cas d'une irradiation par une lumière d'énergie élevée ou dans des conditions de températures élevées. La composition durcissable de l'invention permet une mise en œuvre lors de la formation d'un matériau de fixation d'élément d'éclairage, plus précisément, cette composition est appropriée à une mise en œuvre en tant qu'adhésif pour matériau de fixation d'élément d'éclairage et en tant qu'agent d'étanchéité pour matériau de fixation d'élément d'éclairage.
PCT/JP2011/055273 2010-03-08 2011-03-07 Composition durcissable, produit durci, et procédé de mise en œuvre de composition durcissable WO2011111667A1 (fr)

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JP2017122216A (ja) * 2014-08-26 2017-07-13 リンテック株式会社 硬化性組成物、硬化物、硬化性組成物の使用方法、及び光デバイス
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WO2016031730A1 (fr) * 2014-08-26 2016-03-03 リンテック株式会社 Composition durcissable, procédé de production de composition durcissable, matériau durci, procédé d'utilisation de composition durcissable, et dispositif optique
US9963624B2 (en) 2014-08-26 2018-05-08 Lintec Corporation Curable composition, method for producing curable composition, cured object, method for using curable composition, and optical device
US10266734B2 (en) 2014-08-26 2019-04-23 Lintec Corporation Curable composition, cured product, method for using curable composition, and optical device
US10294398B2 (en) 2014-08-26 2019-05-21 Lintec Corporation Curable composition, method for producing curable composition, cured object, method for using curable composition, and optical device
WO2017192349A1 (fr) 2016-05-03 2017-11-09 Dow Corning Corporation Résine de silsesquioxane et composition d'anhydride de silyle

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JPWO2011111667A1 (ja) 2013-06-27
KR20130034005A (ko) 2013-04-04
CN102906198B (zh) 2014-10-29
TWI504681B (zh) 2015-10-21
KR101768246B1 (ko) 2017-08-14
JP5725479B2 (ja) 2015-05-27
CN102906198A (zh) 2013-01-30

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