WO2015126143A1 - Nouveau composé époxy, mélange, composition et produit durci le comprenant, son procédé préparation, et son utilisation - Google Patents

Nouveau composé époxy, mélange, composition et produit durci le comprenant, son procédé préparation, et son utilisation Download PDF

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Publication number
WO2015126143A1
WO2015126143A1 PCT/KR2015/001605 KR2015001605W WO2015126143A1 WO 2015126143 A1 WO2015126143 A1 WO 2015126143A1 KR 2015001605 W KR2015001605 W KR 2015001605W WO 2015126143 A1 WO2015126143 A1 WO 2015126143A1
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Prior art keywords
formula
group
epoxy
integer
epoxy compound
Prior art date
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Ceased
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PCT/KR2015/001605
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English (en)
Korean (ko)
Inventor
탁상용
전현애
김윤주
박성환
박수진
박숙연
이학준
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Korea Institute of Industrial Technology KITECH
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Korea Institute of Industrial Technology KITECH
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Priority claimed from KR1020140175937A external-priority patent/KR101755323B1/ko
Application filed by Korea Institute of Industrial Technology KITECH filed Critical Korea Institute of Industrial Technology KITECH
Priority to US15/119,977 priority Critical patent/US10597412B2/en
Priority to CN201580020302.8A priority patent/CN106232608B/zh
Priority to JP2016553450A priority patent/JP6423443B2/ja
Publication of WO2015126143A1 publication Critical patent/WO2015126143A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
    • C07D303/26—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds having one or more free hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
    • C07D303/27—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds having all hydroxyl radicals etherified with oxirane containing compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Definitions

  • Novel epoxy compounds mixtures comprising them, compositions. Cured product, preparation method thereof, and use thereof
  • the present invention provides a novel epoxy compound having an effect of improving processability and / or inherent bretttness with excellent heat resistance in a composite that is a cured product of a composition comprising an epoxy compound and a layering agent (fibers and / or inorganic particles). And mixtures, compositions, cured products, preparations thereof, and uses thereof, including the same.
  • the present invention has excellent heat resistance, specifically low thermal expansion properties and high glass transition rate synergistic effects (including Tg lease not exhibiting Yumo transition temperature), flame retardancy and fairness in the composite,
  • the present invention relates to a viscosity controllability, which does not require a separate silane coupling agent, but also to a brittle new epoxy compound having improved brittleness, a mixture, a composition, a cured product, a preparation method thereof, and a use thereof.
  • the epoxy cured product has a large thermal expansion coefficient value of several times to several tens of times that of the ceramic material and the metal material. therefore.
  • an epoxy material is used with an inorganic material or a metal material
  • the physical properties and workability of the part are significantly limited due to the different coefficients of thermal expansion of the epoxy material and the inorganic material or the metal material.
  • CTE-mi sniat ch coefficient of thermal expansion
  • next-generation semiconductor substrate PCB (practed c ircuit t board), packaging, 0 TFT (Organic Thin Film Transistor), and flexible display substrate (FLEXible substrate) are developed.
  • PCB next-generation semiconductor substrate
  • 0 TFT Organic Thin Film Transistor
  • FLEXible substrate flexible display substrate
  • a new epoxy compound and a mixture comprising the same exhibiting improved heat resistance in the composite.
  • a new epoxy compound having excellent processability of the curing reaction and a mixture containing the same are provided.
  • New epoxy compounds exhibiting improved brittleness in composites and mixtures comprising the same are provided.
  • a novel epoxy compound exhibiting excellent flame retardancy in a cured product and a mixture containing the same are provided.
  • the composite exhibits improved heat resistance
  • a method for preparing a new epoxy compound is provided.
  • a method for producing a new epoxy compound having excellent processability of curing reaction is provided. Furthermore, according to another aspect of the present invention, there is provided a method for preparing a new epoxy compound exhibiting improved brittleness in a composite. According to another aspect of the present invention, a method for producing a new epoxy compound exhibiting excellent flame retardancy in a cured product is provided. According to another aspect of the present invention, there is provided a composition (hereinafter referred to as an 'epoxy composition') containing a new epoxy compound exhibiting improved heat resistance in the composite. According to still another aspect of the present invention, an epoxy composition having excellent processability of curing reaction is provided. Furthermore, according to another aspect of the present invention, there is provided an epoxy composition exhibiting improved brittleness in a composite.
  • an epoxy composition exhibiting excellent flame retardancy in a cured product is provided.
  • a cured product of the epoxy composition according to the present invention is provided.
  • the core includes: i) at least two epoxy groups selected from epoxy groups of the formulas E1 and E2 below; i i) at least one alkoxysilyl group selected from the group consisting of the following formulas A1 to A5; And i i i) at least one non-acyclic silyl group selected from the group consisting of the following formulas A6 to A10. Epoxy compounds having alkenyl groups or combinations thereof are provided.
  • Ra, Rb, and RC are each independently H or an alkyl group having 1 to 6 carbon atoms.
  • at least one of R1 to R3 is an alkoxy group having 1 to 6 carbon atoms.
  • An alkyl group having 1 to 10 carbon atoms, the alkyl group and the alkoxy group may be linear or branched, may be cyclic or acyclic, and may or may not have N, 0, S, or P hetero atoms, ni Is an integer from 1 to 10 J
  • Ra, Rb and Rc are each independently H or an alkyl group having 1 to 6 carbon atoms, and in Formulas A6 to A10 R4 to R6 is an aliphatic, alicyclic, or aromatic having 1 to 20 carbon atoms
  • a reactive group, the non-reactive group may be linear or branched, may be cyclic or acyclic,
  • the alkenyl group is provided with an epoxy compound selected from the group consisting of the following formulas (All) to (A13).
  • Ra, Rb, and Rc are each independently H or an alkyl group having 1 to 6 carbon atoms.
  • the alkyl group may be linear or branched, may be cyclic or acyclic, and N, 0, May or may not have S or P hetero atoms, and in formulas A12 and A13, ni is an integer from 1 to 10.
  • the core is the following formulas AC to 0C
  • An epoxy compound, selected from the group consisting of, is provided.
  • K is one of the group consisting of the formula lac to lfc,
  • M is —CH2-, ⁇ C (CH3) 2—, -C (CF3) 2), -S-, -S02-,
  • R is H or C1-C3 alkyl
  • n is an integer of 3 or more.
  • K is lfc, n is an integer of 2 or more,
  • n is an integer of 2 or more
  • n is an integer of 0 or more
  • N 3 or more
  • the cores of the formulas AC to HC are connected to the following linking group LG1, and the formula The core of MC to 0C is provided with an epoxy compound which is connected to the following linker LG2.
  • At least two of the substituents A of Formulas AF to FF are selected from the following Formulas E1 and E2, at least one is selected from the group consisting of Formulas A1 to A3, and the rest of Formulas A6 to A8, It may be independently selected from the group consisting of the formula All. A12, and hydrogen, At least two of the substituents A of the formulas GF to LF are of the formula E1 and at least one of the formulas A2 or A3, and the rest are independently from the group consisting of the formula A7, the formula A8, the formula A12, and hydrogen. Can be selected,
  • At least two of the substituents A of Formulas MF to OF are the following Formula E2, at least one is selected from Formula A4 and Formula A5, and the remainder is composed of Formula A9, Formula A10, Formula A13 and Hydrogen It may be independently selected from the group, in the formula DF, I is -CH2-, -C (CH3) 2-, -C (CF3) 2-, _S—, -S02-, And
  • J is a direct linkage, -CH2- or
  • Rx is H or C1-C3 alkyl group
  • K is the following formula .
  • One of the groups 1A to 1F ' is the following formula .
  • R is H or CI-C3 alkyl, in the above formula IF, when K is 1 ⁇ to IE, n is an integer of 3 or more, and when K is 1F, n is an integer of 2 or more,
  • n is an integer of 2 or more
  • n is an integer greater than or equal to 3
  • N is an integer of 2 or more
  • p is 1 or 2.
  • Ra, Rb, and RC are each independently H or an alkyl group having 1 to 6 carbon atoms
  • at least one of R1 to R3 in Formulas A1 to A5 is an alkoxy group having 1 to 6 carbon atoms, and the rest are carbon atoms.
  • An alkyl group of 1 to 10, wherein the alkyl group and the alkoxy group may be linear or branched, may be cyclic or acyclic, may or may not have N, 0, S. or P hetero atoms, and m is 1 To an integer of 10.
  • Ra, Rb and Rc are each independently H or an alkyl group having 1 to 6 carbon atoms, and in Formulas A6 to A10 R4 to R6 are aliphatic, alicyclic, or aromatic having 1 to 20 carbon atoms Semi-acyclic, the non-acyclic can be linear or branched, cyclic or acyclic,
  • N. 0, S. or P may or may not have a hetero atom, m is an integer from 1 to 10.
  • the epoxy compound is i) at least two epoxy groups represented by the following general formula (E1)
  • Ra, Rb, and RC are each independently H or an alkyl group having 1 to 6 carbon atoms, at least one of R1 to R3 is an alkoxy group having 1 to 6 carbon atoms, and the remainder is an alkyl group having 1 to 10 carbon atoms,
  • the alkyl group and the alkoxy group may be linear or branched, may be cyclic or acyclic, may or may not have N, 0, S, or P hetero atoms, m is an integer of 1 to 10.
  • Ra, Rb, and Rc are each independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be linear or branched, may be cyclic or acyclic, and N, 0, S Or, may or may not have a P hetero atom.
  • an epoxy compound is provided wherein at least one of R 1 to R 3 in the alkoxysilyl group represented by Formulas A1 to A5 is an alkoxy group having 2 to 4 carbon atoms.
  • the chemical formulas A1 to A5 In the alkoxysilyl group to be represented an epoxy compound is provided wherein R 1 to R 3 are hydroxy groups.
  • the epoxy compound of any one of the first aspect to the ninth aspect when the epoxy compound comprises a non-banung silyl group, the ratio of the alkoxysilyl group: the non-banung silyl group is 1: 99 To 99: 1, a mixture of epoxy compounds is provided.
  • a starting material of any one of the following formulas AS1 to 0S1 and an alkoxysilane of the following formula AS5, or an alkoxysilane of the starting material and AS5 and an unreactive silane of the following formula AS6 Provided is a method for producing an epoxy compound of any one of the following formulas AF to OF.
  • R1 to R3 is a C1-C6 alkoxy group, preferably an ethoxy group, and the rest are C1 'C10 alkyl groups.
  • the alkoxy group and alkyl group may be linear or branched, cyclic or non- It may be cyclic and may or may not have N, .S, or P heteroatoms.
  • HSiR4R5R6 (In the formula AS6, R4 to R6 is an alicyclic group which is aliphatic, alicyclic or aromatic having 1 to 20 carbon atoms, the non-reactive group may be linear or branched, cyclic or acyclic, N, It may or may not have 0, S, or P hetero atoms.)
  • At least two of the plurality of substituents al of Formulas AS1 to FS1 may be represented by Formula E1 or Formula E2, at least two may be represented by Formula All or A12, and the remainder may be hydrogen, and substituents of Formula GS1 through LSI
  • At least two of the following formula E1 , at least two of the formula A12, the rest may be hydrogen
  • At least two of the substituents al of the above formulas MSI to 0S1 are the formula E2
  • the rest are the formula A13.
  • Formula DS1 -C (CH3) 2-, -C (CF3) 2-, -S-, -S02-
  • ⁇ J in formula HS1 is a single bond (direct l inkage), -CH2- or
  • Rx is H black is a C1-C3 alkyl group
  • K is one of the groups consisting of the following Formulas lal to 1 ⁇ ,
  • M is —CH2-, -C (CH3) 2 ', -C (CF3) 2-,' S-, 'S02', R is H or C1-C3 alkyl, In formula IS1.
  • K is lal to lei
  • n is an integer of 3 or more
  • n is an integer of 2 or more
  • n is an integer of 2 or more
  • n is an integer of 0 or more
  • n is an integer greater than or equal to 3
  • N is an integer of 2 or more
  • P is 1 or 2 in formula LSI.
  • Ra, Rb, and Rc are each independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be linear or branched, may be cyclic or acyclic, and N, 0, S , Or may or may not have a P hetero atom, and in formula A12 and formula A13, m is an integer from 1 to 10.
  • At least two of the substituents A of Formulas AF to FF are the following Formula E1 or Formula E2, at least one is selected from the group consisting of Formula A1 and Formula A2, the remainder of Formula A6, Formula A7, All, the formula A12 and hydrogen may be selected independently from the group consisting of, At least two of the substituents A of Formulas GF to LF are Formula E1 and at least one is Formula A2, and the rest may be independently selected from the group consisting of Formula A7, Formula A12, and hydrogen.
  • At least two of the substituents A of Formulas MF to OF are the following Formula E2, at least one of the following Formula A4, and the rest may be independently selected from the group consisting of Formula A9, Formula A13, and hydrogen,
  • I is CH2-, —C (CH3) 2 ', -C (CF3) 2-, —S-, -S02-, Is,
  • J is a direct linkage, — CH2- or
  • Rx is H or a C1-C3 alkyl group
  • K is one of the group consist of Formula 1A to 1F to, "
  • Ry is a C1-C10 straight or branched alkyl group.
  • M is -CH2-, -C (CH3) 2-, -C (CF3) 2-, —S_, -S02 ', or CH 3 CH 3,
  • R is H or CI— C3 alkyl, and in the above formula IF, when K is 1 ⁇ to IE, n is an integer of 3 or more, and when K is 1F, n is an integer of 2 or more.
  • N is an integer of 2 or more
  • n is an integer of 0 or more
  • n is an integer of 3 or more.
  • N is an integer of 2 or more
  • p is 1 or 2.
  • Ra, Rb, and RC are each independently H or an alkyl group having 1 to 6 carbon atoms, and at least one of Formulas A1, A2, and A4 messenger, R1 to R3 is an alkoxy group having 1 to 6 carbon atoms. The remainder is an alkyl group having 1 to 10 carbon atoms, and the alkyl group and the alkoxy group may be linear or branched, may be cyclic or acyclic, and may or may not have N, 0, S, or P hetero atoms. , M is an integer of 1 to 10.)
  • Ra, Rb, and Rc are each independently H or an alkyl group having 1 to 6 carbon atoms, and in Formulas A6, A7 and A9, R4 to R6 are aliphatic, alicyclic having 1 to 20 carbon atoms. Or aromatic A non-acyclic group, the non-reactive group may be linear or branched, may be cyclic or acyclic, may or may not have N, 0, S, or P heteroatoms, m is 1 to 10 Is an integer. )
  • Ra, Rb, and Rc are each independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be linear or branched, may be cyclic or acyclic, and N, 0, S Or, with or without a P hetero atom, in formulas A12 and A13 m is an integer from 1 to 10.
  • one equivalent of an alkenyl group of the starting material With respect to the alkoxysilane of the general formula AS5 is 0.1 to 5 equivalents to provide a method for producing an epoxy compound to react the starting material and the alkoxysilane of the general formula AS5.
  • the alkoxysilane of formula AS5 when all of R1 to R3 of the alkoxysilane of formula AS5 are methoxy, the alkoxysilane of formula AS5 is 0.1 to 1 equivalent of alkenyl group of the starting material. There is provided a method for producing an epoxy compound that is reacted to at least 1 equivalent. According to the fourteenth aspect, in the first aspect.
  • the starting material of any one of the formulas AS2 to 0S2 and the alkoxysalane of the formula AS3 Or reacting the starting material with an alkoxysilane of AS3 and a non-acyclic silane of the following formula AS4, a method for producing an epoxy compound of any one of the following formulas AF to OF is provided.
  • R1 to R3 is a C1-C6 alkoxy group, preferably an hydroxy group and the rest is a C1-C10 alkyl group, the alkoxy group and the alkyl group may be linear or branched, cyclic or non May be cyclic and may or may not have N, 0, S. or P heteroatoms, m is an integer from 1 to 10, preferably an integer from 3 to 6.
  • R4 to R6 is an aliphatic group having 1 to 20 carbon atoms, alicyclic, or aromatic, the non-reactive group may be linear or branched, cyclic or acyclic, N , 0, S, or P may or may not have a hetero atom, m is an integer of 1 to 10, preferably an integer of 3 to 6).
  • At least two of the substituents a2 of the above formulas AS2 to FS2 are the following formula E2, at least two are hydroxy groups, and the rest may be independently selected from the group consisting of hydrogen and the formula All below, and the above formulas GS2 to At least two of the substituents a2 of LS2 may be represented by Formula E1, at least two of which are hydroxy groups, and the others may be hydrogen, At least two of the substituents a2 of the formula MS2 to 0S2
  • HS is a single bond (di rect l inkage), -CH2- or
  • Rx is H or C1-C3 alkyl group
  • K is one of the groups consisting of Formulas la2 to If 2
  • M is ⁇ CH2-, -C (CH3) 2-, -C (CF3) 2-, -S-, —S02- , R is H black is C1-C3 alkyl, in the formula IS2, when K is 2a to 2e, n is an integer of 3 or more, when K is 2f, n is an integer of 2 or more, In JS2, n is an integer of 2 or more,
  • n is an integer of 0 or more
  • n is an integer greater than or equal to 3
  • L is. for ⁇ , ⁇ is an integer of 2 or more,
  • P is 1 or 2 in Formula LS2.
  • Ra, Rb and Rc are each independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be linear or branched. It may be cyclic or acyclic, . , N, 0, It may or may not have S, or P hetero atoms.
  • J in formula HF is a direct linkage, -CH2- or
  • Rx is H or a C1-C3 alkyl group
  • K is one of the groups consisting of Formulas 1A ' to 1F,
  • Ry is a C1-C10 straight or branched alkyl group
  • M is -CH2—, -C (CH3) 2-, — C (CF3) 2—, -S-, -S02-, and IT R is H black is C1-C3 alkyl,
  • n is an integer of 3 or more
  • K is 1F
  • n is an integer of 2 or more
  • n is an integer of 2 or more
  • n is an integer of 0 or more
  • N is an integer of 2 or more. 1 or 2 in Formula LF.
  • R1 to R3 is an alkoxy group having 1 to 6 carbon atoms, the remainder is an alkyl group having 1 to 10 carbon atoms, and the alkyl group and the alkoxy group may be linear or branched, and cyclic Or may be acyclic, with or without N, 0, S, or P heteroatoms, m being an integer from 1 to 10.
  • R4 to R6 are aliphatic, cycloaliphatic, or aromatic non-reactive groups having 1 to 20 carbon atoms.
  • the non-reactive groups may be linear or branched, and may be cyclic or acyclic. , N, 0, S, or P with or without a hetero atom, m is an integer from 1 to 10.
  • Ra, Rb, and Rc are each independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be linear or branched, may be cyclic or acyclic, and N, 0, S Or a P hetero atom.
  • the alkoxysilane of the general formula AS3 is 0.1 equivalent to 5 equivalents to 1 equivalent of the hydroxy group or the amine group of the starting material.
  • the alkoxysilane of the formula AS3 when all of R1 to R3 of the alkoxysilane of the above formula AS3 are mesophilic, the alkoxysilane of the formula AS3 has 0.1 equivalent to 1 equivalent of the hydroxy group or the amine group of the starting material.
  • the manufacturing method of the epoxy compound made to react so that it may become less than 1 equivalent or more is provided.
  • an epoxy composition comprising the epoxy compound of any one of the first to ninth aspects.
  • an epoxy composition comprising the epoxy mixture of the tenth aspect. 19
  • the 17th aspect to the 18th aspect to the method glycidyl ether, an epoxy compound, a glycidyl dilgye epoxy compound, glycidyl amine type epoxy compound, glycidyl ester-based epoxy compound, a rubber modified epoxy
  • an epoxy composition further comprising at least one epoxy compound selected from the group consisting of a compound, an aliphatic poly glycidyl-based epoxy compound and an aliphatic glycidyl amine-based epoxy compound.
  • Epoxy compositions having aliphatic or novolak units are provided. According to the 21st opinion, in the 19th opinion.
  • an epoxy composition comprising at least one kind of epoxy compound Owt% to 90wt% selected from the group consisting of epoxy compounds.
  • an epoxy composition further comprising at least one filler selected from the group consisting of inorganic particles or fibers.
  • the inorganic particles are selected from the group consisting of at least one metal oxide selected from the group consisting of silica, zirconia, titania, alumina, silicon nitride and aluminum nitride, and silsesquioxane. VIII is provided with at least one kind of epoxy composition.
  • the fiber is glass fiber and liquid crystal selected from the group consisting of E glass fiber, T glass fiber, S glass fiber, NE glass fiber, H glass fiber, and quartz.
  • Polyester fibers polyethylene terephthalate fibers, wholly aromatic fibers, polybenzoxazole fibers, nylon fibers, polyethylene naphthalate fibers, polypropylene fibers, polyether sulfone fibers, polyvinylidene fluoride fibers, polyethylene sulfide fibers, and poly At least one epoxy composition selected from the group consisting of organic fibers selected from the group consisting of etherether ketone fibers is provided.
  • an epoxy composition further comprising inorganic particles is provided.
  • An electronic material comprising the composition is provided.
  • substrate containing the epoxy composition in any one of 17th to 25th aspect is provided.
  • the film containing the epoxy composition in any one of 17th to 25th is provided. . .
  • an erythrocyte plate comprising a metal layer on a base layer made of the epoxy composition of any one of the seventeenth to twenty-fifth aspects.
  • a printed wiring board comprising the laminated plate of the twenty-ninth aspect.
  • a semiconductor device comprising the printed wiring board of the thirtieth aspect.
  • a semiconductor packaging material comprising the epoxy composition of any one of the seventeenth to twenty-fifth aspects.
  • a semiconductor device including the thirty-second aspect of the semiconductor packaging material.
  • an adhesive comprising the epoxy composition of any of the seventeenth to twenty-fifth aspects.
  • a paint comprising the epoxy composition of any of the seventeenth to twenty-fifth aspects is provided.
  • a composite material is provided of the aspect to the 25th aspect includes any one of an epoxy composition.
  • a prepreg comprising the epoxy composition of any of the thirteenth to twenty fifth aspects.
  • a laminated plate in which a metal layer is disposed in the prepreg of the thirty seventh aspect.
  • cured material of the epoxy composition in any one of 17th to 25th terms is provided.
  • a cured product of an epox composition having a thermal expansion coefficient of 60 ppm / ° C. or less is provided.
  • a cured product of an epoxy composition having a glass transition temperature higher than 100 ° C. or not exhibiting a glass transition temperature is provided.
  • Epoxy compositions comprising the new epoxy compounds according to the invention are characterized in that in composites and / or cured products, the improved heat resistance properties, ie the CTE of the epoxy composites are reduced and the glass transition temperature synergistic effect (which does not exhibit the glass transition temperature) It represents a including a ", the term lease 1)). Furthermore, the hardened
  • composition comprising the epoxy compound of the present invention may be added to the epoxy compound. Due to the improvement of the efficiency of the chemical bonds, the compounding of the silane coupling agent, which is generally formulated in the conventional epoxy composition, is not necessary.
  • Figure 1 (a) is a micrograph (100 times magnification) showing the glass fiber composite surface prepared using Comparative Synthesis Example 1
  • Figure 1 (b) shows the glass fiber composite surface prepared using Synthesis Example 4
  • Micrographs (magnification 100x) are shown.
  • Figure 2 (a) is a micrograph (right, magnification 100 times) showing the sample shape (left) and the internal crack of the composite of the glass fiber composite prepared using Comparative Synthesis Example 2
  • Figure 2 (b) is a comparative synthesis The micrograph (right magnification 100 times) giving the shape of the sample (left) and the surface of the glass fiber composite manufactured using Example 2 is shown.
  • the present invention not only has improved heat resistance at the time of formation of the composite by curing the epoxy composition, in particular low CTE and high Tg (including T g lease) and / or excellent flame resistance in the cured product, but also improves the brittleness of the cured product. And / or to provide a new epoxy compound having excellent curing control properties, for example, viscosity controllability, a method for preparing the same, an epoxy composition and a cured product including the same, and a use thereof.
  • composite refers to a cured product of a composition comprising an epoxy compound and a filler (fibers and / or inorganic particles).
  • cured product refers to a cured product of a composition comprising an epoxy compound, wherein at least one selected from the group consisting of fillers, optional additional curing agents, optional curing catalysts, and other additives, in addition to the epoxy compounds and curing agents.
  • curing agent including a kind is mentioned.
  • the cured product may include a semi-cargo. Generally, only hardened materials reinforced with inorganic particles and / or fibers are called composites.
  • the cured product reinforced with inorganic particles and / or fibers may be understood as having the same meaning in the composite.
  • the new epoxy compounds according to the present invention have reactive and non-react ive groups. Accordingly, upon formation of the composite by curing, the epoxy group reacts with the curing agent to cause curing reaction, and the reactive functional group forms an interfacial bond with the filler (fiber and / or inorganic particle) surface. Thus, it shows a very good chemical bond formation efficiency of the epoxy composite system, and thus, low CTE. And high glass transition temperature synergistic effects (including Tg-less). Therefore, the dimensional stability is improved. In addition, no separate silane coupling agent is required.
  • cured material containing the epoxy compound by this invention shows the outstanding flame retardance.
  • the non-banung functional groups are present as free-ends of the angled moiety to the cured product, thereby improving the viscosity of the curing process and / or brittleness of the final cured product.
  • the reactive functional group is specifically an alkoxysilyl group, and the non-reactive functional group is, for example, an alkylsilyl group.
  • a novel epoxy compound includes at least two epoxy groups in a core; At least one alkoxysilyl group; And at least one and non-reactive silyl groups, alkenyl groups, or a combination thereof.
  • the epoxy group may be independently selected from the following formulas E1 and E2.
  • the alkoxysilyl group is represented by the following formula. At least one selected from the group consisting of A1 to Formula A5.
  • R a . R b and R c are each independently H or an alkyl group having 1 to 6 carbon atoms, in Formulas A1 to A5, at least one of which is an alkoxy group having 1 to 6 carbon atoms, and the rest are alkyl groups having 1 to 10 carbon atoms.
  • the alkyl group and the alkoxy group may be linear or branched, may be cyclic or acyclic, may or may not have N, 0, S, or P heteroatoms, and m is an integer of 1 to 10. to be.
  • the non-reactive silyl group may be any one selected from the group consisting of Formulas A6 to A10.
  • the alkoxysilyl group and the non-acyclic silyl group exhibits the effect of improving the heat resistance property (reducing the CTE and / or increasing the glass transition temperature) as well as viscosity controllability and brittleness improvement effect in the composite intended by the present invention. Is also more preferred within the above preferred range, which is particularly suitable when used in semiconductor packaging.
  • R a , R b and R c are each independently H or an alkyl group having 1 to 6 carbon atoms, and R 4 to 3 ⁇ 4 in Formula A6 to A10.
  • alkenyl group is composed of the following formula All to formula A13 It may be selected from the group.
  • R a , 3 ⁇ 4 and R c are each independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be linear or branched, and cyclic or Can be acyclic, N, 0, S. Or may or may not have a P hetero atom, in which in formulas A12 and A13 m is an integer from 1 to 10.
  • the alkenyl group includes all chemical groups obtained by removing one hydrogen atom from an alkene or a derivative thereof, and includes an allyl group, butenyl group, pentenyl group, and the like, and may be commonly used with them. have. The core.
  • the core is an aromatic core, it may be a kind selected from the group consisting of the following formula AC to 0C.
  • the core is understood to include not only structures represented by the following formulas AC to HC and MC to 0C, but also represented by repeating units such as IC to LC.
  • K is one consisting of the following formula lac to Ifc,
  • M is -CH 2- , -C (CH 3 ) 2- , -C (CF 3 ) 2- , -S-, — Sftr, or And R is H or C1-C3 alkyl.
  • n is an integer of 3 or more
  • K is lfc
  • n is an integer of 2 or more
  • n is an integer of 2 or more.
  • n is an 'integer of 0 or more
  • n 3 or more
  • n is an integer of 2 or more
  • n value is at most 1000.
  • the core is a linking group (LG ) Can be connected. If necessary, 1 to 1,000 core structures may be further connected.
  • the core of the formula AC to HC may be connected to the linking group of the formula LG1 and the core of the formula MC to 0C may be connected to the linking group of the formula LG2.
  • the new epox compound according to one aspect of the present invention may be of formulas AF to OF.
  • At least two of the substituents A of Formulas AF to FF are selected from Formulas E1 and E2, at least one is selected from the group consisting of Formulas A1 to A3, and the rest of Formulas A6 to A8, All. And may be independently selected from the group consisting of formula A12 and hydrogen.
  • At least two of the substituents A of Formulas GF to LF are of Formula E1 and at least one of Formula A2 or Formula A3, and the remainder are independently from the group consisting of Formula A7, Formula A8, Formula A12, and Hydrogen Can be selected.
  • At least two substituents A of Formulas MF to OF are at least one of Formula E2, at least one selected from Formula A4 and Formula A5, and the rest of Formula A9, Formula A10, Formula A13 and hydrogen.
  • I is -CH 2- , -C (CH 3 ) 2- . -C (CF 3 ) 2- , S—, — S0 2-
  • J is a single link (direct linkage).
  • K is one of the group consisting of the formula 1A to 1F
  • M is -C3 ⁇ 4 ⁇ , -C (C3 ⁇ 4) 2- , -C (CF 3 ) 2- , -S-, -S0 2- , or
  • R is H or CI— C3 alkyl.
  • n is an integer of 3 or more
  • n is an integer of 2 or more
  • n is an integer of 2 or more
  • n is an integer of 0 or more
  • n is an integer of 3 or more
  • n is an integer greater than or equal to 2
  • n 1 or 2.
  • the n value is at most 1000.
  • R a , 3 ⁇ 4 and R c in Formula A1 are each independently H or an alkyl group having 1 to 6 carbon atoms, and in Formula A1 to Formula A5, at least one of An alkoxy group having 1 to 6 carbon atoms, the remainder being an alkyl group having 1 to 10 carbon atoms, the alkyl group and the alkoxy group may be linear or branched, cyclic or acyclic, and N, 0, S, or P hetero With or without atoms, m is an integer from 1 to 10
  • R a, 3 ⁇ 4, and R c are each independently H or an alkyl group having 1 to 6 carbon atoms, and in Formulas A6 to A10, R 4 to 3 ⁇ 4 are aliphatic and alicyclic carbon atoms of 1 to 20. Or aromatic non-banung groups, wherein the non-banung groups may be linear or branched, cyclic or acyclic, N, 0, S. Or with or without P heteroatoms, m is an integer from 1 to 10.
  • R a , 3 ⁇ 4 and R c are each independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be linear or branched, may be cyclic or acyclic, and N, 0, It may or may not have an S, or P hetero atom, and in Formulas A12 and A13, ill is an integer from 1 to 10.
  • the epoxy compound is, for example, i) at least two epoxy groups represented by the following general formula E1 in the core [Formula El] ii) at least one alkoxysilyl group represented by the following formula Al
  • R a , R b and 3 ⁇ 4 are each independently H or an alkyl group having 1 to 6 carbon atoms, at least one of Ri to! Is an alkoxy group having 1 to 6 carbon atoms, and the remaining ones have 1 to 10 carbon atoms.
  • An alkyl group, the alkyl group and the alkoxy group may be linear or branched, cyclic or acyclic, and may have N, 0, S, or P heteroatoms, with or without m; Integer;
  • R a , R b and R c are each independently H or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be linear or branched, may be cyclic or acyclic, and 0. S, or P may or may not have an atom ⁇ )
  • the epoxy compound of the present invention is at least one It is preferable to include an alkenyl group.
  • an epoxy mixture comprising the novel epoxy compound according to any aspect of the invention described above.
  • the epoxy compound contains a non-acyclic silyl group in the mixture containing the new epoxy compound of the present invention
  • the ratio of the alkoxysilyl group to the non-reactive silyl group is 1:99 to 99: 1, preferably 5:95. To 95: 5 ratio.
  • Alkoxysilyl group When the ratio of the non-acyclic silyl group is less than 1:99, the concentration of the alkoxysilyl group is too low, and sufficient physical properties may not be secured.
  • the ratio of the alkoxysilyl group to the non-acyclic silyl group is greater than 99: 1, the concentration of the non-reactive silyl group may be too low, and brittleness improvement may not be sufficient.
  • the ratio of the epoxy group: alkoxysilyl group in the mixture containing the new epoxy compound may be 10: 1 to 1:10.
  • the ratio of epoxy group: alkoxysilyl group is less than 1:10, the crosslinking density of the epoxy cured product may be lowered, resulting in deterioration of physical properties, and the ratio of epoxy group: alkoxysilyl group is more alkoxy than 10: 1.
  • the silyl group is small, the effect of improving heat resistance by the alkoxysilyl group may be less.
  • the ratio of the alkoxysilyl group: non-reactive silyl group in the mixture containing the new epoxy compound is 1:99 to 99: 1 ratio, preferably 5:95 to 95: 5 ratio, and the ratio of epoxy group: alkoxysilyl group The ratio is from 10: 1 to 1:10, for example from 1: 1 to 5: 1.
  • the ratio of the alkoxysilyl group to the non-acyclic silyl group and / or the ratio of the epoxy group to the alkoxysilyl group is also preferably as defined above in the epoxy composition of any aspect of the present invention described later. Accordingly, the epoxy compound included in the epoxy composition described later may be the above-described epoxy mixture.
  • the alkoxysilane of the starting material and the alkoxy of the general formula AS5 is present in an amount of 0.1 to 5 equivalents of the alkoxysilane of the formula AS5 with respect to 1 equivalent of the alkenyl group of the starting material. It is preferable to react the silane, and the reaction rate of the alkoxysilyl group and the degree of silylation in the final structure are too high when the alkoxysilane of the formula AS5 is reacted to less than 0.1 equivalent to 1 equivalent of the alkenyl group of the starting material.
  • the alkoxysilane of Formula AS5 When the alkoxysilane of Formula AS5 is reacted with more than 5 equivalents to 1 equivalent of alkenyl group of the starting material, there is a problem that the concentration of the unalcoated alkoxysilyl group is excessively increased. .
  • the amount of alkoxysilane of the above formula AS5 to 0.1 equivalent or more is less than 1 equivalent to 1 equivalent of the alkenyl group of the starting material. It is preferable.
  • Epoxy compound Reactions by-products that do not conform to the definition can be obtained in the state of the mixture.
  • the ratio of the alkoxysilyl group: non-inert non-reactive silyl group and / or the ratio of the epoxy group: alkoxysilyl group may be in the above-described range, and the mixture of such epoxy compounds may be described later by itself. It can be used in epoxy compositions.
  • alkoxy group is a monovalent group that is -OR (R is an alkyl group), which may be linear or branched.
  • alkyl group refers to a monovalent hydrocarbon group, which may be straight or branched chain, in the formulas described above or below, where there are a plurality of substituents, each substituent May be independently selected, for example, when the substituents A or more of Formulas AF to FF are selected from Formulas A1 to A3, a plurality of As are each independently selected from Formulas A1 to A3.
  • R1 to R3 of A2 may be the same or different
  • the epoxy compound according to one aspect of the present invention is a composite of a composition comprising the same.
  • the cross-linking network in the cured product is present in the suspended part (dangled moiety), improves the viscosity and / or the final cured product of the curing process through this brittle.
  • Epoxy compounds of the formula (AF) to OF according to one aspect of the invention It can be synthesized in two ways as follows. That is, the epoxy compound of the present invention is a method through hydrosilylation of a double bond, the method (method 1), or a hydroxy group and / or amine by alkoxysilylation and non-reactive silylation of the epoxy compound having an epoxy group and an alkenyl group As a method through reaction of a group with an isocyanate chalan coupling agent, it can be synthesized by a method (method 2) by silylating an epoxy compound having an epoxy group and a hydroxy group or an amine group.
  • the epoxy compound of the present invention is prepared by alkoxysilylation and non-axially silylation of an alkenyl group of an epoxy compound having an epoxy group and an alkenyl group as starting materials.
  • the epoxy compound having the epoxy group and the alkenyl group is hereinafter referred to as starting material for convenience.
  • the starting material may specifically be a compound of Formulas AS1 to 0S1.
  • At least two of the plurality of substituents al of Formulas AS1 to FS1 may be Formula E1 or Formula E2, at least two are Formula All or A12, and the remainder may be hydrogen. At least two of the substituents al of the above formulas GS1 to LSI are
  • E1 at least two of which are Formula A12, and the rest may be hydrogen. At least two of the substituents al of the above formulas MSI to 0S1 are the formula E2, and the rest are the formula A13. At least two of the substituents al of the formulas MS1 to 0S1 are the formula E2, and the rest are the formula A13. -, -C ((3 ⁇ 4) 2- , -C (CF 3 ) 2- , -S-, -S0 2- ,
  • J is a single bond (direct l inkage), -CH 2 — or
  • Rx is H black is a C1-C3 alkyl group
  • K is one of the groups consisting of the following Formulas lal to lfl,
  • M is -CH 2 —, -C (CH 3 ) 2- , -C (CF 3 ) 2 —, -S-, ⁇ S0 2 —, and And R is H or C1-C3 alkyl.
  • R is H or C1-C3 alkyl.
  • n is an integer of 2 or more
  • n is an integer of 0 or more
  • n is an integer of 3 or more
  • n is an integer greater than or equal to 2 and in the above formula LSI, p is 1 or 2.
  • the n value is at most 1000. .
  • at least two epoxy groups, at least one alkoxysilyl group, and at least one albino in accordance with one aspect of the present invention by alkoxysilylating and non-reactive silylating the alkenyl group of the starting material in the presence of a platinum catalyst and any solvent Epoxy compounds having male functional groups, specifically non-reactive silyl groups and alkenyl groups, are obtained.
  • the alkenyl of the starting material is taken into consideration.
  • the starting material and the alkoxysilane of the formula AS5 are reacted such that the alkoxysilane of the formula AS5 is 0, 1 to 5 equivalents.
  • the alkoxysilane of the above formula AS5 has an amount of 0.01 equivalent or more but less than 1 equivalent to 1 equivalent of the alkenyl group of the starting material. It is preferable to make it.
  • At least one of 3 ⁇ 4 to 3 ⁇ 4 is a C1-C6 alkoxy group, preferably an ethoxy group and the rest is a C1-C10 alkyl group, the alkoxy group and the alkyl group may be linear or branched, cyclic or non And may or may not have N, 0, S, or P heteroatoms.
  • the starting material and the non-reactive silane are equivalent ratios of the alkenyl group and the non-reactive silane of the starting material according to the stoichiometry.
  • the starting material and the non-acyclic silane of the following formula AS6 are reacted with respect to 1 equivalent of the alkenyl group of the starting material so that the non-reactive silane of the formula AS6 has 0.1 to 5 equivalents.
  • R 4 to R 6 is an aliphatic, alicyclic, or aromatic non-reactive group having 1 to 20 carbon atoms, the non-banung group may be linear or branched chain
  • the non-banung group may be linear or branched chain
  • the reaction of the starting material with the alkoxysilane and the non-aromatic silane may be carried out at the same time as (1) the starting material, the alkoxysilane and the non-acyclic silane, and (2) after reacting the starting material and the alkoxysilane,
  • the reaction product obtained in situ can also be counter reacted with the non-banung silane.
  • the reaction between the starting material and the alkoxysilane is different depending on the reactant degree and reaction time, for example, may be reacted for 1 to 72 hours at -20 ° C to 120 ° C. By reacting with the reaction and the reaction time, the desired reaction can be completed.
  • Platinum catalysts include, but are not limited to, platinum catalysts of, for example, Pt3 ⁇ 4 or H 2 PtCl 6 (Chloropl at inic ac id). Platinum catalyst is based on 1 equivalent of alkenyl group of starting material. It is preferable to use 1 ⁇ 10—4 to 0.05 equivalent in terms of reaction efficiency.
  • the solvent may optionally be used as necessary.
  • the solvent may not be used if the viscosity of the reaction product is suitable for the reaction to proceed in the reaction product without any solvent. That is, if the viscosity of the reaction product is low enough so that the mixing and stirring with the reactants can proceed smoothly without a solvent, a separate solvent is not required, which can be easily determined by those skilled in the art.
  • a solvent as a possible solvent, the reaction product can be dissolved well, and any aprotic solvent can be used as long as it can be easily removed after the reaction without any adverse effect on the reaction. For example, but not limited to, toluene, acetonitrile, tetrahydrofur anth (THF).
  • Methyl ethyl ketone (MEK), dimethyl formami de (DMF), dimethyl sul foxi de). Methylene chloride (MC) And the like can be used. These solvents may be used alone or in combination of two or more in width.
  • the amount of the solvent used is not particularly limited and may be used in a suitable amount and / or concentration within a range in which the reactants are sufficiently dissolved and do not adversely affect the reaction, and those skilled in the art can select appropriately. have. Equal
  • reaction scheme in the process of producing a new epoxy compound by the production method according to the invention described in the parentheses Reactions such as these are produced together. Unreacted starting materials may also be common.
  • the starting materials can also be synthesized according to any method known in the art. For example, it may be synthesized by the method disclosed in the Korean Patent Application No. 2012-93320. 2013-11711, 2013-27308, 2013-35546, 2013-78347 and 2013-111473 filed by the present applicant, the patent application The content disclosed in is incorporated herein by reference.
  • the epoxy compound of the present invention is prepared by alkoxysilylation and non-reactive silylation of an epoxy group as starting material and an alkenyl group of an epoxy having a hydroxy group or an amine group.
  • the starting material which is an epoxy compound having the epoxy group and the hydroxy group or the amine group may specifically be a compound of Formulas AS2 to 0S2.
  • At least two of the substituents a2 of Formulas AS2 to FS2 may be represented by Formula E2, at least two are hydroxyl groups, and the others may be independently selected from hydrogen and Formula All.
  • At least two of the substituents a2 of Formula GS2 to LS2 may be represented by the above Formula
  • I represents C-, -C (CH 3 ) 2- , -C (CF 3 ) 2- , -S-, —S0 2 ,
  • J in formula HS2 is a direct linkage, -CH 2 -or
  • Rx is H black is a C1-C3 alkyl group
  • K is one of the groups consisting of Formulas la2 to H2
  • L in Formula LS2 is Alkyl group.
  • M is- ( 3 ⁇ 4-, one C (CH 3 ) 2- , — C (CF 3 ) 2 — .-S-, _S0 2 _, or ! 3 and R is H or C1-C3 alkyl.
  • n is an integer of 3 or more
  • K is 2f
  • n is an integer of 2 or more
  • n is an integer of 2 or more
  • n is an integer of 0 or more
  • n is. Is an integer greater than or equal to 3
  • N is an integer of 2 or more
  • the n value is up to 1000.
  • at least two epoxy groups, at least one alkoxysilyl group, and at least one non-banening functional group according to one aspect of the present invention by alkoxysilylating and non-banning silylating the hydroxy or amine group of the starting material in the presence of any solvent
  • An epoxy compound having (specifically, non-banung silyl group and alkenyl group) is obtained.
  • the starting material and the alkoxysilane react with the hydroxy group or the amine group of the starting material in an equivalent ratio according to the stoichiometry, the hydroxy group or the amine group 1 equivalent of the starting material is The starting material is reacted with the alkoxysilane of formula AS3 such that the alkoxysilane is from 0.1 equivalent to 5 equivalents.
  • the alkoxysilane of the above formula AS3 may be 0.01 or more and less than 1 equivalent to 1 equivalent of the hydroxy or amine group of the starting material. It is preferable to react.
  • At least one of 3 ⁇ 4 to R 3 is a CI—C6 alkoxy group, preferably an hydroxy group, and the rest are C1-C10 alkyl groups, and the alkoxy group and the alkyl group may be linear or branched, cyclic or non- May be cyclic, N. It may or may not have a 0, S, or P hetero atom.
  • m is an integer of 1-10, Preferably it is an integer of 3-6.
  • the starting material and the non-reflective silane are reacted at the equivalence ratio according to the stoichiometry of the hydroxy group or the amine group of the starting material.
  • the starting material and the non-acyclic silane of the general formula AS4 are reacted with respect to 1 equivalent of the hydroxy group or the amine group of the starting material such that the amount of the non-acyclic silane of the general formula AS4 is from 0.1 equivalent to 5 equivalents.
  • R 4 to 3 ⁇ 4 are aliphatic, alicyclic, having 1 to 20 carbon atoms, Or an aromatic non-acyclic group, wherein the non-reactive group may be linear or branched, may be cyclic or acyclic, and may or may not have N, 0, S, or P hetero atoms.
  • m is an integer of 1-10, Preferably it is an integer of 3-6.
  • the reaction of the starting material, the alkoxysilane and the non-coagulant silane may be carried out simultaneously with (1) the starting material, the alkoxysilane and the non-coagulant silane, and (2) the reaction of the starting material with the alkoxysilane, and then The reaction product obtained subsequently in can also be reacted with non-reactive silane.
  • the reaction between the starting materials and the alkoxysilanes varies in degree and reaction time depending on the reaction product, for example. Can be reacted at 20 ° C. to 120 ° C. for 1 to 72 hours. By reacting with the reaction temperature and reaction time, the desired reaction can be completed.
  • the above reaction in connection with the process for producing the epoxy compound of the present invention can be carried out in the presence of a base if necessary.
  • the reaction proceeds without the use of a separate base, but in this case the reaction rate is slow, and the reaction rate can be increased by using a base.
  • the base that can be used include, but are not limited to, K 2 CO 3 , Na 2 CO 3 , KHC0 3 , NaHCOs, triethylamine, diisopropylethylamine, and the like. These bases may be used alone or in combination of two or more.
  • the base may be used in an amount of 1 to 5 equivalents based on 1 equivalent of the hydroxy group or the amine group of the starting material in terms of reaction efficiency.
  • the solvent may optionally be used, if necessary.
  • the solvent may not be used if the viscosity of the reactants at the reaction temperature is suitable for the reaction to proceed even without a separate solvent in the reaction step. That is, when the viscosity of the reaction product is low enough that the mixing and stirring of the reaction product can proceed smoothly without solvent, No solvent is required. This can be easily determined by those skilled in the art.
  • any aprotic solvent as a possible solvent, any aprotic solvent (as long as it can dissolve the reaction product well and can be easily removed after the reaction without any adverse effect on the reaction). aprotic solvents) may be used.
  • toluene acetonitrile, THF tetra hydro furan, ⁇ (methyl ethyl ketone), dimethyl formamide (DMF), dimethyl sul foxide (MMS), and methylene chloride (MC) may be used.
  • solvents may be used alone or in combination of two or more thereof.
  • the amount of the solvent used is not particularly limited and may be used in a suitable amount in a range in which the reaction product is sufficiently dissolved and does not adversely affect the reaction, and those skilled in the art may appropriately select it.
  • the reaction scheme of the novel epoxy compound according to the present invention is as follows.
  • the starting material has an amine group
  • reaction byproducts such as are produced together.
  • Mibanung's starting material can also be common. have.
  • the starting materials can also be synthesized according to any method known in the art.
  • the present invention may be synthesized by the method disclosed in the Korean Patent Application No. 2012-93320, 2013-11711, 2013-27308, 2013-35546, 2013-78347 and 2013-111473 filed by the present applicant, the patent application The content disclosed in is incorporated herein by reference.
  • an epoxy composition comprising the new epoxy compound provided by any aspect of the present invention.
  • Any of the compositions provided in the present invention may be used for electronic materials, for example, but not limited to, electronic materials such as semiconductor substrates, for example, IC substrates, build-up films, encapsulation materials (packaging materials), and printed wiring boards. It can be used for various uses such as parts, adhesives, paints, composite materials.
  • any of the compositions provided in the present invention may be a curable composition comprising a curable composition and / or an inorganic material.
  • epoxy compositions including at least one new epoxy compound selected from the group consisting of the formulas (AF) to (OF)
  • any type and / or combination of epoxy compositions known in the art is included, and constitutes an epoxy composition. It does not limit the kind and compounding ratio of the hardening
  • epoxy compositions, cured products and / or composites may be used with various kinds of conventional epoxy compounds in terms of property control, depending on their application and / or use.
  • the epoxy compound is at least one new epoxy S) " selected from the group consisting of the above formulas AF to OF according to one aspect of the invention.
  • the 'epoxy compound of the present invention' may also include any kind of epoxy compound known in the art (hereinafter, also referred to as a conventional epoxy compound).
  • the compound is not particularly limited and may be any epoxy compound known in the art, for example, glycidyl ether epoxy compound, glycidyl epoxy compound, glycidylamine epoxy compound, glycidyl Ester Epoxy Compound Rubber Modified Epoxy Compound, Aliphatic Poly Glycidyl Epoxy Compound And an aliphatic glycidyl amine-based epoxy compound, and at least one selected from the group consisting of an aliphatic glycidyl amine-based epoxy compound.
  • the conventional epoxy compound has a core structure of bisphenol, biphenyl, naphthalene, benzene, thiodiphenol and fluorene (fl uorene).
  • Glycidyl ether epoxy compound glycidyl epoxy compound, glycidyl amine epoxy compound, glycidyl ester epoxy compound, rubber modified epoxy compound, aliphatic poly glycidyl epoxy compound and aliphatic glycid having unit
  • Silver core structure is bisphenol, biphenyl, naphthalene, fluorene, benzene, thiodiphenol, fluorene (f luorene), anthracene, isocyanurate, triphenylmethane, 1, 1, 2, 2-tetrapheny
  • Any epoxy composition in accordance with one aspect of the present invention comprises 1 to 100 wt% of the epoxy compound of the present invention and 0 to 99 wt% of the conventional epoxy compound based on the total weight of the epoxy compound; For example, 10 to 100 wt% of the epoxy compound of the present invention and 0 to 90 wt% of the conventional epoxy compound; E.g .
  • the epoxy compound of the present invention may include less than 50 to 100 wt and more than 0 to 50% by weight of the conventional epoxy compound.
  • the epoxy compositions of any aspect of the invention described above and below may further include inorganic materials (fillers) (eg, inorganic particles and ' / it fibers).
  • inorganic particles any inorganic particles known to be used to reinforce the physical properties of the organic resin may be used, but are not limited thereto.
  • Silica including, for example, fused silica and crystalline silica. At least one metal oxide selected from the group consisting of zirconia, titania, alumina, silicon nitride and aluminum nitride. And. At least one selected from the group consisting of silsesquioxanes can be used.
  • the inorganic particles may be used alone or in combination of two or more thereof.
  • fused silica can be used in both a crushed form and a spherical form, in order to raise the compounding quantity of fused silica and to suppress the raise of the melt viscosity of a molding material. It is preferable to use a spherical one.
  • the inorganic particles include, but are not limited to, inorganic particles having a particle size of 0.5 nm to several tens (for example, 50 to 100) in consideration of the use of the composite, specifically, the dispersibility of the inorganic particles .
  • the inorganic particles may be suitably added depending on the appropriate viscosity and use required for reducing and applying CTE of the epoxy composite.
  • the content of the inorganic particles is 5 wt% to 95 wt%, for example 5 wt% to 90 wt V, for example 10 wt%, based on the total amount of solids of the epoxy composition (based on the total weight of the epoxy cured product in the case of epoxy cured products).
  • To 90 wt% for example. 30 wt% to 95 wt%, for example, 30 wt% to 90 wt%, for example 5 wt to 60 wt%, for example, 10 wt% to 50 wt%.
  • the content of the inorganic particles in consideration of the CTE value and the material processability is, for example, the total solid content of the epoxy composition.
  • weight based on the total weight of the epoxy cured product in the case of epoxy cured products it may be from 30 wt% to 95 wt%, for example from 30 wt% to 90 wt%.
  • the content of the inorganic particles in consideration of the CTE value and the strength of the substrate is, for example, based on the weight of the total solid content of the epoxy composition (for epoxy cured products). 5 wt% based on the total weight of the cured epoxy To 85 wt%, for example, 10 wt% to 80 wt%.
  • the size of the fiber is not particularly limited, and any kind and dimension of fibers generally used in the art may be used. Can be.
  • the fiber is not limited thereto, and any fiber generally used for improving physical properties of the cured organic resin may be used. Specifically, glass fibers, organic fibers or mixtures thereof may be used. Also.
  • the term 'glass fiber' is used to mean not only glass fiber, but also glass fiber fabric, glass fiber nonwoven fabric, and the like.
  • glass fibers include E glass fibers, T glass fibers, S glass fibers, NE glass fibers, D glass fibers, quartz glass fibers, and the like, for example, E or T Glass fiber can be mentioned as an example.
  • Liquid crystalline polyester fiber polyethylene terephthalate fiber, wholly aromatic fiber, polybenzoxazole fiber.
  • Nylon fiber polyethylene naphthalate fiber, polypropylene fiber.
  • At least one species selected from the group consisting of polyether sulfone fibers, polyvinylidene fluoride fibers, polyethylene sulfide fibers, and polyetheretherketone fibers may be used alone or in combination of two or more thereof.
  • the fiber content is 10 wt% to 90 wt%, for example 30 wt% to 70 wt%, also for example based on the total weight of the cured product. , 35 wt% to 70%. Therefore, the resin content is 10wt% to 90wt%, for example, 30wt% to 70wt%, and for example, 35wt% to about 7 (1 ⁇ 21;.% May be that the content of fiber of the above range, improvement in heat resistance and In terms of processability, on the other hand, in an epoxy composition containing a fiber, a cured product, etc., the solid part of the total solid other than the fiber is generally resin.
  • any aspect of the epoxy composition comprising the fibers may further include inorganic particles, if necessary.
  • the inorganic particles may be blended in an amount ranging from 1 wt% to 80 wt% based on the weight of the total resin content in consideration of improvement of physical properties and fairness.
  • the type of inorganic particles that can be used is not particularly limited, any inorganic particles known in the art can be used, for example, the type of the inorganic particles can be used.
  • the epoxy composition of any aspect of the present invention described above and below may further include a curing agent.
  • any curing agent generally known as a curing agent for an epoxy compound may be used.
  • the curing agent may be, for example, an amine, a polyphenol, an acid anhydride, or the like. More specifically, the present invention is not limited thereto, and examples of the amine curing agent include aliphatic amines, cycloaliphatic amines, aromatic amines, other amines, and modified polyamines.
  • An amine compound including two or more primary amine groups may be used.
  • amine curing agent examples include 4,4'-dimethylaniline (diamino diphenyl methane) (4, 4'-D i me t hy 1 an i 1 i ne (di am i no diphenyl methane, DAM or DDM ), One or more aromatic amines, diethylenetriamines (diamino diphenyl sulfone (DDS), m- phenylene di ⁇ ] ⁇ min (m- pheny lene diamine) diethylene tri amine (DETA), diethylene tetramine, tri ethylene tetraamine (TETA), m—xylene diamine (MXDA), methane di amine (MDA) ), N, N'-diethylenediamine (N, N'- diethy 1 enedia ine, N, N'-DEDA), tetraethylenepentaainine (TEPA), and nucleomethylenediamine at least one alipha
  • polyphenol curing agent examples include, but are not limited to, phenol novolac resins, cresol novolac resins, bisphenol A novolac resins, xylene novolac resins, triphenyl noblock resins, biphenyl novolac resins and dicyclopentadiene nos. Volac resin, naphthalene novolak resin, etc. are mentioned.
  • acid anhydride curing agents include, but are not limited to, aliphatic acid anhydrides such as dodecenyl succinic anhydride (DDSA), poly azelaic poly anhydr icle, and nucleohydrophthalic anhydrides.
  • Cycloaliphatic acid anhydrides such as lead (hexahydrophthalic anhydride (HHPA), methyl tetrahydrophthalic anhydride (MeTHPA), methylnadic anhydride (MNA)), trimellitic anhydride ( Aromatic acid anhydrides such as trimellitic anhydride (TMA), pyroniellitic acid di anhydride (PMDA), benzophenonetetracarboxylic acid] ⁇ . (Benzophenonetetracarboxyl ic di anhydride, BTDA), tetrabromophthalic anhydride Such as tetrabrOTophthalic anhydride (TBPA), chlorendic anhydride, etc. And the like halogen acid anhydride.
  • HHPA hexahydrophthalic anhydride
  • MeTHPA methyl tetrahydrophthalic anhydride
  • MNA methylnadic anhydride
  • trimellitic anhydride Aromatic acid anhydrides such as trimellitic
  • the degree of curing of the epoxy composite may be adjusted to the extent of reaction between the curing agent and the epoxy group, and the content of the curing agent may be adjusted based on the concentration of the epoxy group of the epoxy compound according to the desired degree of curing.
  • amine In the case where a curing agent is used, in the equivalent reaction of the amine curing agent and the epoxy group, it is preferable to adjust the content of the curing agent so that the epoxy equivalent / amine equivalent ratio is 0.5 to 2.0, and for example, 0.8 to 1.5. .
  • curing agent was demonstrated using the case of an amine hardening
  • Acid curing agent and any curing agent that can be used to cure the epoxy compounds not separately described herein also depend on the concentration of the total epoxy groups in the epoxy composition, depending on the desired degree of cure, and the chemical reaction formula of the reactive functional groups of the epoxy functional group and the curing agent. Can be suitably combined in stoichiometric amounts according to the invention, which is common in the art.
  • the imidazole described below is widely used as a curing accelerator, but may also be used as a single curing agent. When imidazole is used as a curing agent, an amount of 0.1 to lOphr is used relative to the epoxy compound.
  • Epoxy compositions of any aspect of the invention described above and below may further comprise optional curing accelerators (curing catalysts) as necessary to promote curing reactions.
  • curing accelerator any catalyst known in the art to be generally used for curing an epoxy composition may be used, but is not limited thereto.
  • imidazole, tertiary amine, fourth Curing accelerators such as quaternary ammonium, organic acid salts, Lewis acids, phosphorus compounds and the like can be used.
  • dimethyl benzyl amine 2-methylimidazole (2MZ), 2-undecylimidazole, 2-ethyl-4'methylimidazole (2E4M), 2-phenylimidazole Imidazoles such as 1- (2-cyanoethyl) -2—alkyl group imidazole and 2-heptadecylimidazole (heptadecyl imi dazol e, 2HDI); Tertiary amine compounds such as benzyl dimethyl amine (BDMA), trisdimethylaminomethylphenol (DMP-30), diazabicycloundecene (DBU) and triethylenediamine; Quaternary ammonium salts such as tetrabutylammonium bromide; DBU's Organic acid salts; Phosphoric compounds such as triphenylphosphine and phosphate ester, Lewis acids such as BF 3 -monoethyl amine (BFVMEA),
  • hardening accelerators ⁇ may be used that have been latent in their microcapsule coating and complex salt formation. These may be used independently and may use 2 or more types together according to hardening conditions.
  • the compounding quantity of the said hardening accelerator is not specifically limited, It can mix
  • the epoxy compound may be 0.1 to 10 phr (part s per hundred res in, parts by weight per 100 parts by weight of epoxy compound), for example, 0.2 to 5 phr.
  • the curing accelerator is preferably used in the above content in terms of curing reaction promoting effect and curing reaction rate control.
  • the epoxy composition is a release agent, surface treatment agent, flame retardant, plasticizer, antimicrobial agent, leveling agent, antifoaming agent, colorant, stabilizer, coupling agent, viscosity, which is conventionally formulated to control the physical properties of the epoxy composition within a range that does not impair the physical properties of the epoxy composition
  • Other additives such as regulators, diluents, rubbers, thermoplastics, etc. may also be blended as needed.
  • rubber and / or thermoplastic resins may be added to any aspect of the present invention to impart solubility to any composition according to the present invention.
  • Thermoplastic resins and rubber-modified epoxy resins can be used that are generally known in the art.
  • the rubber any rubber known in the art may be used as long as it is not dissolved in the solvent used in the composition and remains dispersed in the composition.
  • the type of rubber is, for example, acrylonitrile butadiene rubber ⁇ butadiene rubber, acrylic rubber, core-shell rubber particles, crosslinked acrylonitrile butadiene rubber particles, crosslinked styrene butadiene Rubber particles, acrylic rubber, particles, and the like. These may be used alone or in combination of two or more.
  • the average particle diameter is preferably in the range of 0.005.
  • the rubber particles may be blended at, for example, 0.5 to 10% by weight, in consideration of physical properties based on the weight of the solid content of the epoxy composition.
  • Thermoplastic resins include, but are not limited to, phenoxy resins, polyvinyl acetal resins, polyimide resins, polyamideimide resins, polyether sulfone resins. Polysulfone resin etc. are mentioned. These may be used alone or in combination of two or more.
  • the thermoplastic resin may be blended in an amount of, for example, from 0.5 to 60% by weight, preferably from 3 to 50% by weight, based on the weight of the solid content of the epoxy composition.
  • epoxy composition refers to the epoxy compound of the present invention as well as other components constituting the epoxy composition as needed, for example, any curing agent, curing accelerator (catalyst). It is understood that other additives may be formulated as needed in the art, other than inorganic materials (fillers) (eg, inorganic particles and / or fibers), other conventional epoxy compounds and solvents, and therefore The solvent in the epoxy composition may optionally be used to suitably adjust the solids content and / or viscosity of the epoxy composition in consideration of the processability of the epoxy composition and the like. Meanwhile.
  • total weight of solids of the epoxy composition refers to the total weight of the components excluding the solvent among the components constituting the epoxy composition.
  • Any epoxy composition provided in any aspect of the present invention may be used for electronic materials.
  • the electronic material is not limited to this, but for example.
  • Made of a substrate, film, prepreg, or composition of the present invention In addition to the laminate and the sealing material (packaging material) in which the metal layer is disposed on the base material layer.
  • It is an electronic component such as a printed wiring board. It can also be applied to various applications such as adhesives, paints and composite materials.
  • an electronic material comprising or consisting of any composition comprising the epoxy compound of the present invention.
  • the semiconductor device comprising, consisting essentially of or consisting of the electronic material.
  • the semiconductor device may include a semiconductor device and / or a semiconductor packaging material including (eg, mounting a semiconductor device) a printed wiring board including, or consisting essentially of, a composition comprising the epoxy compound of the present invention. It may be a semiconductor device including.
  • the cured product comprising, consisting essentially of or consisting of any epoxy composition provided in any aspect of the invention. Adhesives, paints or composites are provided.
  • a cured product comprising, consisting essentially of, or consisting of the epoxy composition provided in any aspect of the invention described above.
  • the epoxy composition provided in any aspect of the present invention is used as a cured product when it is actually applied, for example, as an electronic material, and includes an epoxy compound and a filler which is an inorganic component in the art.
  • the cured product of the composition is generally referred to as a composite.
  • the epoxy compound provided in one aspect of the present invention exhibits excellent heat resistance properties in the composite and / or excellent flame resistance in the cured product.
  • the composite may have a low CTE, for example, 15 p irc or less, for example, 12 ppm / ° C or less, for example, 10 ppm / ° C or less, for example, 8 ppm / ° C or less, for example, 6 ppm / ° C or less, for example, 4 ppm / ° C or less.
  • any epoxy compound according to the present invention as an epoxy compound.
  • a composite comprising inorganic particles, for example, 60 to 80 wt%, for example 70 to 80 wt%, as an inorganic material is at most 20 p ii / ° C., for example at most 15 pp / ° C., for example, 10 ppm / ° C or less, for example, 8 ppm / ° C or less, for example, 6 ppm / ° C or less, for example 4 ppm / ° C or less.
  • the composite according to the present invention (cured product including an inorganic material) has a Tg higher than 100 ° C., for example, 130 ° C.
  • the epoxy compound self-cured product (cured material containing no inorganic material) according to the present invention has a CTE of 50 ppm / ° C. to 150 ppm / ° C.
  • the value indicated by the range means each including not only the lower limit and the upper limit of the range, but also any lower range between the ranges and all the numbers belonging to the range.
  • C 10 is CI. C2, C3, C4, C5, C6, C7. It is understood to include all of C8, C9, C10.
  • naphthalene epoxy (formula 2) having an allyl group, 9.82 ml of triethisilane, 121 mg of platinum oxide, and 100 ml of toluene were mixed and mixed in a 500 ml flask, and filled with argon for 24 hours at 85 ° C. Stirred. After the reaction, the crude product obtained was filtered through Celite and the solvent was removed using an evaporator to obtain a final epoxy. N dried data of the obtained final product is as follows.
  • the temperature was 85 ° C. and heated and stirred for 24 h.
  • the obtained crude product was filtered through Celite and the solvent was removed using an evaporator to obtain a final epoxy having a concentration ratio of epoxy group: epoxysilyl group: allyl group of 1: 1: 1.
  • the NMR data of the obtained final product is as follows.
  • the temperature was 85 ° C. and heated and stirred for 24 h.
  • the obtained crude product was filtered through Celite and the solvent was removed using an evaporator to obtain a final epoxy having a concentration ratio of epoxy group: ethoxysilyl group: allyl group of 1: 1: 1.
  • the NMR data of the obtained final product is as follows /
  • N dried data of the obtained final product is as follows.
  • the VII R data of the final product obtained is as follows.
  • an epoxy compound, a silica slurry (solid content of 70 wt%, 2-methoxyethanol solvent, silica average size of l ⁇ m) and polyvinyl acetal are dissolved in methyl ethyl ketone so that the solid content is 40%.
  • a curing agent was added and the mixture was further mixed for 50 minutes.
  • a glass fiber composite was prepared by immersing glass fiber (Nittobo Glass fiber fabric T-glass) in the epoxy mixture.
  • the resin content of the composite film was adjusted according to the pressure of the press and the viscosity of the resin, and the resin content in the composite film is shown in Table 1 below.
  • thermo-mechanical analyzer Thermo-niechanical Analysizer
  • Epoxy compounds with (Comparative synthesis example 2) are geotgwak as shown in Figure 2, the curing rate. Too fast (br i tt le) because the sample produced is too weak. It was not possible to manufacture glass fiber composites that could be sampled. However, when an allyl group is present in the epoxy compound having a methoxysilyl group, the cured product is brittle. If improved (FIG. 2 (b)) and an evaluable glass fiber composite was produced, no crack was observed on the surface of the cured product.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)

Abstract

La présente invention concerne un nouveau composé époxy, son procédé de préparation, une composition et un produit durci le comprenant, et son utilisation, le composé présentant d'excellentes propriétés de résistance à la chaleur, plus particulièrement, une propriété de dilatation thermique faible et une température de transition vitreuse élevée (y compris sans Tg qui ne présente pas de température de transition vitreuse), une propriété d'ignifugation et d'aptitude à la transformation, plus particulièrement, une propriété de régulation d'épaississement sans nécessiter d'agent séparé de couplage au silane, et présente une fragilité améliorée dans un complexe. Selon un aspect de la présente invention, l'invention concerne : un composé époxy ayant au moins un groupe silyle non réactif, un groupe alcényle ou une combinaison de ces derniers conjointement à au moins deux groupes époxy et au moins un groupe alcoxysilyle ; un procédé de préparation du composé époxy à travers l'alkoxysilylation et l'alkylsilylation ; une composition époxy le comprenant; et un produit durci. La composition époxy comprenant le nouveau composé époxy de la présente invention présente des propriétés améliorées de résistance à la chaleur, c'est-à-dire, un effet d'augmentation de la température de transition vitreuse et un Coefficient de Dilatation Thermique (CDT) réduit du complexe époxy en raison de la formation d'une liaison chimique par l'intermédiaire d'une réaction chimique entre le groupe alcoxysilyle et une charge et d'une réaction chimique entre les groupes alcoxysilyle dans le complexe et/ou un produit durci. En outre, le produit durci de la composition époxy selon la présente invention présente une excellente propriété d'ignifugation en raison de l'introduction du groupe alcoxysilyle. En outre, l'épaississement de la composition époxy de la présente invention peut être facilement régulé au cours d'une réaction de durcissement. En outre, le produit durci de la composition époxy présente une fragilité réduite.
PCT/KR2015/001605 2014-02-19 2015-02-17 Nouveau composé époxy, mélange, composition et produit durci le comprenant, son procédé préparation, et son utilisation Ceased WO2015126143A1 (fr)

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US15/119,977 US10597412B2 (en) 2014-02-19 2015-02-17 Epoxy compound, mixture, composition, and cured product comprising same, method for preparing same, and use thereof
CN201580020302.8A CN106232608B (zh) 2014-02-19 2015-02-17 环氧化合物，含所述环氧化合物的混合物、组合物和固化产物，及其制备方法和应用
JP2016553450A JP6423443B2 (ja) 2014-02-19 2015-02-17 新規のエポキシ化合物、それを含む混合物、組成物、硬化物、その製造方法、及びその用途

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KR1020140175937A KR101755323B1 (ko) 2014-02-19 2014-12-09 신규한 에폭시 화합물, 이를 포함하는 혼합물, 조성물, 경화물, 이의 제조 방법, 및 이의 용도
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JP2018100236A (ja) * 2016-12-20 2018-06-28 Dic株式会社 ナフタレン型エポキシ化合物の製造方法及びナフタレン型エポキシ化合物
JP2021046449A (ja) * 2020-12-25 2021-03-25 Dic株式会社 ナフタレン型エポキシ化合物の製造方法及びナフタレン型エポキシ化合物

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JPH06345847A (ja) * 1993-06-07 1994-12-20 Shin Etsu Chem Co Ltd エポキシ樹脂組成物及び半導体装置
KR20110043719A (ko) * 2008-10-22 2011-04-27 디아이씨 가부시끼가이샤 경화성 수지 조성물, 그 경화물, 프린트 배선 기판, 에폭시 수지, 및 그 제조 방법
KR20130135733A (ko) * 2012-06-01 2013-12-11 한국생산기술연구원 알콕시실릴기를 갖는 에폭시 화합물, 무기입자를 포함하는 조성물, 경화물, 이의 용도 및 알콕시실릴기를 갖는 에폭시 화합물의 제조방법

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US5336786A (en) * 1992-12-07 1994-08-09 Shin-Etsu Chemical Company, Limited Organic silicon compounds
JPH06345847A (ja) * 1993-06-07 1994-12-20 Shin Etsu Chem Co Ltd エポキシ樹脂組成物及び半導体装置
KR20110043719A (ko) * 2008-10-22 2011-04-27 디아이씨 가부시끼가이샤 경화성 수지 조성물, 그 경화물, 프린트 배선 기판, 에폭시 수지, 및 그 제조 방법
KR20130135733A (ko) * 2012-06-01 2013-12-11 한국생산기술연구원 알콕시실릴기를 갖는 에폭시 화합물, 무기입자를 포함하는 조성물, 경화물, 이의 용도 및 알콕시실릴기를 갖는 에폭시 화합물의 제조방법

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Publication number Priority date Publication date Assignee Title
JP2018100236A (ja) * 2016-12-20 2018-06-28 Dic株式会社 ナフタレン型エポキシ化合物の製造方法及びナフタレン型エポキシ化合物
JP2021046449A (ja) * 2020-12-25 2021-03-25 Dic株式会社 ナフタレン型エポキシ化合物の製造方法及びナフタレン型エポキシ化合物
JP7038385B2 (ja) 2020-12-25 2022-03-18 Dic株式会社 ナフタレン型エポキシ化合物の製造方法及びナフタレン型エポキシ化合物

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