WO2022210189A1 - Catalyseur de durcissement, composition de résine, matériau d'étanchéité, adhésif, et produit durci - Google Patents

Catalyseur de durcissement, composition de résine, matériau d'étanchéité, adhésif, et produit durci Download PDF

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WO2022210189A1
WO2022210189A1 PCT/JP2022/013646 JP2022013646W WO2022210189A1 WO 2022210189 A1 WO2022210189 A1 WO 2022210189A1 JP 2022013646 W JP2022013646 W JP 2022013646W WO 2022210189 A1 WO2022210189 A1 WO 2022210189A1
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manufactured
resin composition
compound
mercaptomethylthio
resin
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Japanese (ja)
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友也 中井
理恵子 永田
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ナミックス株式会社
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Priority to CN202280009235.XA priority Critical patent/CN116745281A/zh
Priority to KR1020237020573A priority patent/KR20230161929A/ko
Priority to JP2023511074A priority patent/JPWO2022210189A1/ja
Publication of WO2022210189A1 publication Critical patent/WO2022210189A1/fr

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    • C—CHEMISTRY; METALLURGY
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
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    • 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
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    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62—Alcohols or phenols
    • C08G59/621—Phenols
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    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/66—Mercaptans
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    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/08—Saturated oxiranes
    • C08G65/10—Saturated oxiranes characterised by the catalysts used
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3445—Five-membered rings
    • C—CHEMISTRY; METALLURGY
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L35/02—Homopolymers or copolymers of esters
    • 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
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C—CHEMISTRY; METALLURGY
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    • C08G2170/00—Compositions for adhesives
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2190/00—Compositions for sealing or packing joints

Definitions

  • the present invention relates to curing catalysts, resin compositions, sealing materials, adhesives, and cured products.
  • a one-component adhesive contains a main agent and a curing catalyst, or a main agent, a curing agent, and a curing catalyst. Cure catalysts are believed to have the greatest impact on the pot life and cure conditions of adhesives.
  • the purpose of the present invention is to provide novel curing catalysts, resin compositions, sealing materials, adhesives, and cured products.
  • One embodiment of the present invention is a curing catalyst comprising a compound of structural formula (I) below.
  • R 1 is a group selected from hydrogen, phenyl and C1-C17 alkyl
  • R 2 , R 3 , R 5 are each independently a group selected from hydrogen and C1-C6 alkyl
  • R4 is a group selected from hydrogen, OH and OAc (Ac: abbreviation for acetyl group)
  • n and m are integers, the sum of which is 1 or more and 12 or less or 1 or more and 3 or less.
  • thermosetting resin may be an epoxy resin.
  • the thermosetting resin may be a compound having a polymerizable double bond.
  • a curing agent for the thermosetting resin may be further included.
  • the curing agent may be one selected from the group consisting of oxygen-containing compounds, nitrogen-containing compounds, and thiol compounds.
  • a further embodiment of the present invention is a sealing material, adhesive, or cured product containing any of the above resin compositions.
  • a further embodiment of the present invention is a compound of structural formula (I) below.
  • R 1 is a group selected from phenyl and C1-C17 alkyl
  • R 2 , R 3 , R 5 are each independently a group selected from hydrogen and C1-C6 alkyl
  • R4 is a group selected from OH and OAc
  • n and m are integers, the sum of which is 1 or more and 12 or less.
  • R 1 is a group selected from phenyl and C1-C10 alkyl
  • R 2 , R 3 , R 5 are hydrogen, R4 is OH
  • n and m may be one.
  • the present invention has made it possible to provide novel curing catalysts, resin compositions, sealing materials, adhesives, and cured products.
  • R 1 is a group selected from phenyl and C1-C17 alkyl
  • R 2 , R 3 , R 5 are each independently a group selected from hydrogen and C1-C6 alkyl
  • R4 is a group selected from OH and OAc
  • n and m are integers, the sum of which is 1 or more and 12 or less, preferably 6 or less, more preferably 3 or less.
  • R 1 is preferably selected from phenyl and C1-C11 alkyl.
  • R 2 , R 3 and R 5 are preferably hydrogen.
  • R4 is preferably OH.
  • n and m are each 1.
  • the term "curing catalyst” means a catalyst having a function of promoting the initiation and/or progress of polymerization when the main agent is self-polymerized or when the main agent and the curing agent are polymerized. do.
  • the curing catalyst may be incorporated only at the terminal of the polymer.
  • R 1 is a group selected from hydrogen, phenyl and C1-C17, preferably C1-C11 alkyl
  • R 2 , R 3 , R 5 are each independently a group selected from hydrogen and C1-C6 alkyl
  • R4 is a group selected from hydrogen, OH and OAc
  • n and m are integers, the sum of which is 1 or more and 12 or less, preferably 6 or less, more preferably 3 or less.
  • More preferably, the sum of n and m is 1 when R4 is hydrogen, and both n and m are 1 when R4 is OH.
  • this curing catalyst has a phthalimide skeleton, it is difficult for the curing catalyst to dissolve in the resin in an unintended temperature range in the resin composition, the pot life becomes longer, and it is useful as a curing catalyst for thermosetting resins. is.
  • the curing catalyst disclosed herein may contain one or more compounds having the structural formula (I). It may also contain one or more curing catalysts other than the compound having structural formula (I).
  • the resin is not particularly limited, but a thermosetting resin is preferred.
  • epoxy resins and compounds having a polymerizable double bond group for example, (meth)acrylic compounds and maleimide compounds
  • (meth)acrylic compounds and maleimide compounds can be exemplified.
  • acryl and methacryl are collectively referred to as (meth)acryl.
  • Epoxy resin The epoxy resin is not particularly limited, and may be a monofunctional epoxy resin or a multifunctional epoxy resin.
  • a monofunctional epoxy resin is an epoxy resin having one epoxy group, and has been conventionally used as a reactive diluent to adjust the viscosity of an epoxy resin composition.
  • Monofunctional epoxy resins are roughly classified into aliphatic monofunctional epoxy resins and aromatic monofunctional epoxy resins. From the viewpoint of volatility, the monofunctional epoxy resin preferably has an epoxy equivalent of 180 to 400 g/eq.
  • aromatic monofunctional epoxy resins include phenyl glycidyl ether, cresyl glycidyl ether, p-s-butylphenyl glycidyl ether, styrene oxide, p-tert-butylphenyl glycidyl ether, o-phenylphenol glycidyl ether, m- Examples include, but are not limited to, phenylphenol glycidyl ether, p-phenylphenol glycidyl ether, N-glycidyl phthalimide, and the like.
  • p-tert-butylphenyl glycidyl ether and phenyl glycidyl ether are preferred, and p-tert-butylphenyl glycidyl ether is particularly preferred.
  • aliphatic monofunctional epoxy resins include n-butyl glycidyl ether, 2-ethylhexyl glycidyl ether, ⁇ -pinene oxide, allyl glycidyl ether, 1-vinyl-3,4-epoxycyclohexane, 1,2-epoxy-4 -(2-methyloxiranyl)-1-methylcyclohexane, 1,3-bis(3-glycidoxypropyl)-1,1,3,3-tetramethyldisiloxane, neodecanoic acid glycidyl ester, etc. can be, but are not limited to:
  • a polyfunctional epoxy resin is an epoxy resin having two or more epoxy groups. Accordingly, the resin composition of the present disclosure may include difunctional epoxy resins, trifunctional epoxy resins, tetrafunctional epoxy resins, and the like. Polyfunctional epoxy resins are roughly classified into aliphatic polyfunctional epoxy resins and aromatic polyfunctional epoxy resins.
  • aliphatic polyfunctional epoxy resins examples include (poly)ethylene glycol diglycidyl ether, (poly)propylene glycol diglycidyl ether, butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether.
  • diepoxy resins such as ether, trimethylolpropane diglycidyl ether, polytetramethylene ether glycol diglycidyl ether, glycerin diglycidyl ether, neopentyl glycol diglycidyl ether, cyclohexane type diglycidyl ether, dicyclopentadiene type diglycidyl ether; Triepoxy resins such as methylolpropane triglycidyl ether, glycerin triglycidyl ether; vinyl (3,4-cyclohexene) dioxide, 2-(3,4-epoxycyclohexyl)-5,1-spiro-(3,4-epoxy Cycloaliphatic epoxy resins such as cyclohexyl)-m-dioxane; glycidylamine type epoxy resins such as tetraglycidylbis(aminomethyl)cyclohexane; h
  • cyclohexane-type diglycidyl ether means that two glycidyl groups are each bonded via an ether bond to a divalent saturated hydrocarbon group having one cyclohexane ring as a base structure.
  • a compound having a structure is meant.
  • dicyclopentadiene-type diglycidyl ether refers to a compound having a structure in which two glycidyl groups are each bonded via an ether bond to a divalent saturated hydrocarbon group having a dicyclopentadiene skeleton as a base structure. means.
  • cyclohexane-type diglycidyl ether cyclohexanedimethanol diglycidyl ether is particularly preferred.
  • Aromatic polyfunctional epoxy resins are polyfunctional epoxy resins having a structure containing aromatic rings such as benzene rings. Many conventional epoxy resins, such as bisphenol A type epoxy resin, are of this type. Examples of aromatic polyfunctional epoxy resins include bisphenol A type epoxy resins; branched polyfunctional bisphenol A type epoxy resins such as p-glycidyloxyphenyldimethyltrisbisphenol A diglycidyl ether; bisphenol F type epoxy resins; type epoxy resin; bisphenol S type epoxy resin; novolac type epoxy resin; tetrabromobisphenol A type epoxy resin; fluorene type epoxy resin; biphenyl aralkyl epoxy resin; ,3′,5,5′-tetramethyl-4,4′-diglycidyloxybiphenyl; diglycidylaniline, diglycidyltoluidine, triglycidyl-p-aminophenol, tetraglycidyl-m- glycidylamine-type epoxy resins
  • aromatic polyfunctional epoxy resins bisphenol F-type epoxy resins, bisphenol A-type epoxy resins and glycidylamine-type epoxy resins are preferable, and among them, those having an epoxy equivalent of 90 to 200 g/eq are preferable.
  • the polymer compound having a polymerizable double bond group is not particularly limited.
  • compounds having an alkyl group include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, normal butyl acrylate, normal Butyl methacrylate, normal hexyl acrylate, normal hexyl methacrylate, normal heptyl acrylate, normal heptyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, normal lauryl acrylate, lauryl methacrylate, stearyl acrylate, stearyl methacrylate, etc.; compounds having cyclohexyl acrylate, cyclohexyl methacrylate, isobornyl acrylate, isobornyl methacrylate, isobornyl methacryl
  • trimethylolpropane triacrylate pentaerythritol triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, ditrimethylolpropane tetraacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol hexaacrylate.
  • Multifunctional (meth)acrylates of polyol derivatives such as; Pentaerythritol triarylate, pentaerythritol tetraarylate, trimethylolpropane triarylate and other polyfunctional arylates; Aronix M-7100, Aronix M-8030, Aronix M-8060 polyester (meth)acrylates such as Toagosei Co., Ltd.; Co., Ltd.), Aronix M-305, Aronix M-309, Aronix M-310, M-315, M-320, Aronix M-350, Aronix M-360, Aronix M-370, Aronix M-400, Aronix M-402, Aronix M-408, Aronix M-450, (all manufactured by Toagosei Co., Ltd.), Neomer TA-401, TA-505, EA-301, DA-600 (both Sanyo Chemical Industries Co., Ltd.) ), NK Ester A-TMPT, NK Ester
  • compounds having a maleimide group include N,N'-(4,4'-diphenylmethane)bismaleimide, bisphenol A diphenyletherbismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'- Diphenylmethanebismaleimide, 4-methyl-1,3-phenylenebismaleimide, 1,6'-bismaleimido-(2,2,4-trimethyl)hexane, bis-(3-ethyl-5-methyl-4-maleimidophenyl) ) methane, m-phenylenebismaleimide (N,N′-1,3-phenylenebismaleimide), 1,6-bismaleimidohexane, 1,2-bismaleimidoethane (N,N′-ethylenedimaleimide), N,N'-(1,2-phenylene)bismaleimide, N,N'-1,4-phenylenedimaleimide, N,N'-(sulfonyl
  • dimer acid-modified bismaleimide It is also possible to use dimer acid-modified bismaleimide.
  • dimer acid-modified bismaleimides include liquid bismaleimides BMI-689, BMI-1500 and BMI-1700, and solid bismaleimides BMI-3000 (all manufactured by Designer Molecules).
  • the resin composition of the present disclosure may contain one or more curing agents.
  • Curing agents that may be contained in the resin composition of the present disclosure are not particularly limited, but include, for example, nitrogen-containing compounds such as amines and their derivatives; , oxygen-containing compounds such as phenol-terminated epoxy resins; sulfur-containing compounds such as thiol compounds.
  • Nitrogen-containing compounds such as amines and derivatives thereof are not particularly limited, but aliphatic polyamines such as triethylenetetramine, tetraethylenepentamine, m-xylenediamine, trimethylhexamethylenediamine, and 2-methylpentamethylenediamine, isophorone diamine.
  • Epomic Q-640 Epomic Q-643 (Mitsui Chemicals, trade name), DETDA80 (Lonza, trade name), Thothamine HM-205 (Nippon Steel & Sumikin Chemical Co., Ltd., trade name), etc. is mentioned.
  • the acid anhydride-based curing agent is not particularly limited, but for example, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, alkylated tetrahydrophthalic anhydride, methylhimic acid anhydride, alkenyl-substituted Succinic anhydride, glutaric anhydride and the like can be mentioned.
  • Phenolic curing agents refer to monomers, oligomers, and polymers generally having phenolic hydroxyl groups, such as phenol novolac resins and their alkylated or allylated products, cresol novolak resins, phenol aralkyl (including phenylene and biphenylene skeleton) resins, and naphthol aralkyls. Resins, triphenol methane resins, dicyclopentadiene type phenol resins, and the like. Among them, allylphenol novolac resin is preferable.
  • Thiol compounds include hydrolyzable polyfunctional thiol compounds and non-hydrolyzable polyfunctional thiol compounds.
  • hydrolyzable polyfunctional thiol compounds include trimethylolpropane tris(3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: TMMP), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanate Nurate (manufactured by SC Organic Chemical Co., Ltd.: TEMPIC), pentaerythritol tetrakis (3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: PEMP), tetraethylene glycol bis (3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.) : EGMP-4), dipentaerythritol hexakis (3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: DPMP), pentaerythritol tetrakis (3-mercaptobutyrate) (manu
  • non-hydrolyzable polyfunctional thiol compounds include 1,3,4,6-tetrakis(2-mercaptoethyl) glycoluril (trade name: TS-G, manufactured by Shikoku Kasei Co., Ltd.), (1,3, 4,6-tetrakis(3-mercaptopropyl)glycoluril (trade name: C3 TS-G, manufactured by Shikoku Kasei Co., Ltd.), 1,3,4,6-tetrakis(mercaptomethyl)glycoluril, 1,3,4 ,6-tetrakis(mercaptomethyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(2-mercaptoethyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(3-mercapto Propyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(mercaptomethyl)-3a,6a-dimethylglycoluril,
  • non-hydrolyzable polyfunctional thiol compound it is also possible to use a trifunctional or higher polythiol compound having two or more sulfide bonds in the molecule.
  • thiol compounds include 1,2,3-tris(mercaptomethylthio)propane, 1,2,3-tris(2-mercaptoethylthio)propane, 1,2,3-tris(3-mercapto propylthio)propane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane, 4,7- dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane, tetrakis(mercaptomethylthiomethyl) Methane
  • the ratio of the curing catalyst in the resin composition is not particularly limited, it is preferably 0.01 to 50 wt%, more preferably 0.01 to 30 wt%, relative to the thermosetting resin in the resin composition. More preferably, it is 0.01 to 20 wt%.
  • the pot life is defined as the time until the thickening ratio of the resin composition doubles from the initial value, and the pot life in the epoxy-thiol curing system is preferably 8 hours or longer, more preferably 12 hours or longer. , more preferably 16 hours or longer. Also in other curing systems, a longer pot life is preferable from the viewpoint of stability.
  • the curable composition of the present disclosure may optionally contain, for example, the following in addition to the main agent, curing catalyst, and curing agent.
  • Stabilizer A stabilizer can be added to the resin composition of the present disclosure in order to improve its storage stability and prolong its pot life.
  • Various known stabilizers can be used as stabilizers for one-component adhesives based on epoxy resins. preferable.
  • liquid borate compounds examples include 2,2′-oxybis(5,5′-dimethyl-1,3,2-oxaborinane), trimethylborate, triethylborate, tri-n-propylborate, triisopropylborate, tri - n-butylborate, tripentylborate, triallylborate, trihexylborate, tricyclohexylborate, trioctylborate, trinonylborate, tridecylborate, tridodecylborate, trihexadecylborate, trioctadecylborate, tris(2 -ethylhexyloxy)borane, bis(1,4,7,10-tetraoxaundecyl)(1,4,7,10,13-pentoxatetradecyl)(1,4,7-trioxaundecyl) Borane, tribenzylborate, triphenylborate,
  • aluminum chelate for example, aluminum chelate A (manufactured by Kawaken Fine Chemicals Co., Ltd.) can be used.
  • organic acid for example, barbituric acid can be used.
  • filler A filler can be added to the resin composition of the present disclosure.
  • fillers include silica fillers, glass fillers, alumina fillers, titanium oxide fillers, boron nitride fillers, aluminum nitride fillers, talc fillers, calcium carbonate fillers, resin fillers (e.g., polytetrafluoroethylene (PTFE) fillers, silicone rubber fillers, etc.), conductive fillers such as silver, copper and nickel.
  • the shape is not particularly limited, and may be hollow, spherical, or amorphous.
  • the filler may be surface-treated.
  • Coupling agent A coupling agent can be added to the resin composition of the present disclosure.
  • the coupling agent is preferably a silane coupling agent, and various silane coupling agents such as epoxy, amino, vinyl, methacrylic, acrylic, and mercapto can be used. These silane coupling agents may be used alone or in combination of two or more.
  • Silane coupling agents include, for example, vinyltrimethoxysilane (commercially available from Shin-Etsu Chemical Co., Ltd.; KBM-1003, Momentive Performance Materials Japan Co., Ltd.; A -171, Dow Corning Toray Co., Ltd.; Z-6300, Asahi Kasei Wacker Silicone Co., Ltd.; GENIOSIL XL10, Himi Shoji Co., Ltd.; KBE-1003, Momentive Performance Materials Japan; A-151, Dow Corning Toray; Z-6519, Asahi Kasei Wacker Silicone; GENIOSIL GF56, Himi Shoji; Sila Ace S220, etc.
  • vinyltriacetoxysilane commercially available from Asahi Kasei Wacker Silicone; GENIOSIL GF62
  • vinyltris(2-methoxyethoxy)silane commercially available from Momentive Performance Materials Japan
  • A-172 vinylmethyldimethoxysilane
  • commercially available products include Momentive Performance Materials Japan; A-2171, Asahi Kasei Wacker Silicone; GENIOSIL XL12, etc.
  • octenyltri Methoxysilane commercially available from Shin-Etsu Chemical Co., Ltd.; includes KBM-1083
  • allyltrimethoxysilane commercially available from Dow Corning Toray; includes Z-6825
  • p-styryltrimethoxysilane Commercially available products include KBM-1403 manufactured by Shin-Etsu Chemical Co., Ltd.).
  • silane coupling agents having an acrylic group include 3-acryloxypropyltrimethoxysilane, 3-acryloxypropyltriethoxysilane (commercially available products manufactured by Shin-Etsu Chemical Co., Ltd.; KBM-5103, etc.), and the like.
  • silane coupling agents having a methacryl group include 3-methacryloxypropylmethyldimethoxysilane (commercially available products manufactured by Shin-Etsu Chemical Co., Ltd.; KBM-502, Toray Dow Corning Co., Ltd.; Z-6033, etc.).
  • 3-methacryloxypropyltrimethoxysilane (commercially available from Shin-Etsu Chemical Co., Ltd.; KBM-503, Momentive Performance Materials Japan Co., Ltd.; A-174, Dow Corning Toray Co., Ltd.; Z-6030 , Asahi Kasei Wacker Silicone Co., Ltd.; GENIOSIL GF31, Himi Shoji Co., Ltd.; Sila Ace S710, etc.), 3-methacryloxypropylmethyldiethoxysilane (commercially available products include Shin-Etsu Chemical Co., Ltd.; KBE-502.
  • N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane manufactured by Shin-Etsu Chemical Co., Ltd.; KBM-602; Asahi Kasei Wacker Silicone Co., Ltd.; GENIOSIL GF-95, Himi Shoji Co.; Sila Ace S310, etc.
  • N-2-(aminoethyl)-3-aminopropyltrimethoxysilane commercially available from Shin-Etsu Chemical KBM-603, Momentive Performance Materials Japan; A-1120, Momentive Performance Materials Japan; A-1122, Dow Corning Toray; Z-6020, Dow Toray Z-6094 manufactured by Corning Corporation; Z-6094 manufactured by Asahi Kasei Wacker Silicone Co., Ltd.; GENIOSIL GF-91 manufactured by Himi Shoji Co.; KBM-903, manufactured by Momentive Performance Materials Japan; A-1110, manufactured by Dow Corning Toray Co.,
  • KBM-802 manufactured by Dow Corning Toray; Z-6852, etc.
  • 3-mercaptopropyltrimethoxysilane commercially available from Shin-Etsu Chemical Co., Ltd.; KBM-803, Momentive Performance Materials Co., Ltd.; A-189 manufactured by Japan Co., Ltd.; Z-6062 manufactured by Dow Corning Toray; Sila Ace S810 manufactured by Himi Shoji Co., Ltd.; A-1891 manufactured by Dow Corning Toray Co., Ltd.; Z-6911 manufactured by Toray Dow Corning Co., Ltd.; Shin-Etsu Chemical Co., Ltd.; includes KBE-585), 3-ureidopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane (commercially available from Momentive Performance Materials Japan; A-1160).
  • examples of the silane coupling agent having a sulfide group include bis(triethoxysilylpropyl) tetrasulfide
  • examples of the silane coupling agent having a thioester group include 3-octanoylthio-1-propyltriethoxysilane (Commercially available products include A-LINK599 manufactured by Momentive Performance Materials Japan), and have an isocyanate group.
  • 3-isocyanatopropyltriethoxysilane (commercially available products include KBE-9007 manufactured by Shin-Etsu Chemical Co., Ltd., A-1310 manufactured by Momentive Performance Materials Japan, etc.), 3 -Isocyanatopropyltrimethoxysilane (commercially available products include Y-5187 manufactured by Momentive Performance Materials Japan, GENIOSIL GF40 manufactured by Asahi Kasei Wacker Silicone Co., Ltd.) and the like.
  • the resin composition of the present disclosure may contain other additives such as carbon black, titanium black, ion trapping agents, leveling agents, antioxidants, digestive agents, etc., within a range that does not impair the object of the present invention.
  • Foaming agents, thixotropic agents, viscosity modifiers, flame retardants, coloring agents, solvents and the like can be added.
  • the type and amount of each additive are as per conventional methods.
  • the resin composition disclosed herein can be used, for example, as sealing materials and fillers for electronic components, dam materials, conductive or insulating adhesives, die attach materials, films, coating agents, shielding materials, and the like. can. In addition, it can be used for paints, composite materials such as pipe materials and tank materials, floor materials, civil engineering and construction materials such as membranes, adhesives, and the like, but the usage is not limited to these.
  • Denacol EX-731 (manufactured by Nagase ChemteX Corporation, 100 g, 0.363 mmol) was gradually added to the resulting solution over about 10 minutes. After dissolving everything, the mixture was heated to 70° C. and stirred at the same temperature for 6 hours. After cooling to room temperature, water (about 200 mL) was added and stirred to precipitate crystals. The resulting solid was suction filtered, washed twice with water and twice with IPA, and then dried to obtain compound 1 (85.7 g) (61% recovery).
  • the measured physical properties of the product are as follows.
  • 2-Methyl-1H-imidazole (manufactured by Shikoku Kasei Co., Ltd., 21.8 g, 266 mmol) was dissolved in a mixed solvent of toluene (78.7 mL) and methanol (17.7 mL), heated to 80° C., and Denacol EX was prepared.
  • a toluene (38.1 mL) solution of -141 (manufactured by Nagase ChemteX Corporation, 22.0 g, 147 mmol) was added dropwise over 1 hour, followed by stirring at the same temperature for 1 hour.
  • Table 1 shows the evaluation results of the compounds.
  • PEMP manufactured by SC Organic Chemical Co., Ltd.
  • SC Organic Chemical Co., Ltd. which is a thiol resin
  • stirring and defoaming were performed under vacuum to obtain a resin composition.
  • Epoxy-thiol curing system Compound 1 as a curing catalyst was added to a mixture obtained by dispersing EXA835LV and TS720 (manufactured by Cabot Specialty Chemicals) using a three-roll mill and mixed. Thereafter, the mixture was ground in a mortar until no aggregation occurred, and stirred and defoamed under vacuum using a planetary stirring and defoaming device. C3TSG (manufactured by Shikoku Kasei Kogyo Co., Ltd.), which is a thiol resin, was added thereto and mixed. Then, using a planetary stirring and defoaming device, stirring and defoaming were performed under vacuum to obtain a resin composition.
  • EXA835LV and TS720 manufactured by Cabot Specialty Chemicals
  • Examples 7, 11, 12 Epoxy homopolymerization curing system> Compound 1, compound 5, and compound 6 as curing catalysts were put into EXA835LV and mixed. Thereafter, the mixture was ground in a mortar until no aggregation occurred, and stirred and defoamed under vacuum using a planetary stirring and defoaming apparatus to obtain a resin composition.
  • Epoxy-acid anhydride curing system Compound 1 as a curing catalyst was put into EXA835LV, which is an epoxy resin, and mixed. Thereafter, the mixture was ground in a mortar until no aggregation occurred, and stirred and defoamed under vacuum using a planetary stirring and defoaming apparatus. Then, YDF8170 (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.) was added and mixed. Thereafter, stirring and defoaming were performed under vacuum using a planetary stirring and defoaming device.
  • EXA835LV an epoxy resin
  • Epoxy-phenol curing system > Compound 1 as a curing catalyst was added to EXA835LV and mixed. Thereafter, the mixture was ground in a mortar until no aggregation occurred, and stirred and defoamed under vacuum using a planetary stirring and defoaming device. EXA835LV was put in there and mixed. Thereafter, stirring and defoaming were performed under vacuum using a planetary stirring and defoaming device. Furthermore, MEH8005 (manufactured by Meiwa Kasei Co., Ltd.), which is a phenolic resin, was added and mixed. Then, using a planetary stirring and defoaming device, stirring and defoaming were performed under vacuum to obtain a resin composition.
  • MEH8005 manufactured by Meiwa Kasei Co., Ltd.
  • Acrylic-thiol curing system > M7100 (manufactured by Toagosei Co., Ltd.) as an acrylic resin, OMNIRAD184 (manufactured by IGM resins B.V.) as a photoradical generator, Q-1301 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) as a polymerization inhibitor, and a stabilizing agent.
  • TS720 was dispersed with a three-roll mill as a component, and compound 1 as a curing catalyst was added to the resulting mixture and further dispersed with a three-roll mill. After PEMP was added thereto and mixed, stirring and defoaming were performed under vacuum using a planetary stirring and defoaming device to obtain a resin composition.
  • the time before gelation (referred to as gel time) was measured using a gelation tester (GT-D-15A: manufactured by Eucalyptus Giken Co., Ltd.).
  • a hot plate was set to 100° C., 120° C., or 150° C., and the resin composition was transferred onto the hot plate using a test rod.
  • the gel time was defined as the time from touching the resin composition with a test rod until it became stringy.
  • Comparative Example 2 has a high melting point, it has a low molecular weight, so it is easily dissolved in epoxy resins and the like, and lacks stability.
  • a comparison of the pot life of the resin composition revealed that the comparative examples were already cured in 4 hours, whereas the viscosity increase rate doubled in all the examples in 8 hours or longer.
  • the resin composition in the example gelled within 10 minutes and had sufficient reactivity and curability.
  • the curing catalyst of the present disclosure has a phthalimide skeleton, so it has high crystallinity and a higher melting point than the conventional adducts obtained by adding an epoxy resin and an imidazole derivative. , a stable resin composition is obtained in which the curing catalyst is less likely to dissolve in the resin at unintended temperatures.

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  • Polymers & Plastics (AREA)
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Abstract

L'objectif de la présente invention est de fournir un nouveau catalyseur de durcissement, une nouvelle composition de résine, un nouveau matériau d'étanchéité, un nouvel adhésif, et un nouveau produit durci. Un catalyseur de durcissement ayant un composé selon la formule structurale (I) est utilisé. (Dans la formule, R1 est un groupe choisi parmi de l'hydrogène, du phényle, et des alkyles en C1-C17, R2, R3, et R5 sont chacun indépendamment des groupes choisis parmi de l'hydrogène et des alkyles en C1-C6, R4 est un groupe choisi parmi de l'hydrogène, OH, et OAc, n et m sont des nombres entiers, et la somme de n et m est comprise entre 1 et 12.)
PCT/JP2022/013646 2021-03-30 2022-03-23 Catalyseur de durcissement, composition de résine, matériau d'étanchéité, adhésif, et produit durci WO2022210189A1 (fr)

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KR1020237020573A KR20230161929A (ko) 2021-03-30 2022-03-23 경화 촉매, 수지 조성물, 봉지재, 접착제 및 경화물
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JPS58172392A (ja) * 1982-04-02 1983-10-11 Hidetoshi Tsuchida シクロデキストリン包接イミダゾ−ル配位ヘム錯体およびガス吸脱着剤
WO1988008840A1 (fr) * 1987-05-04 1988-11-17 Centre National De La Recherche Scientifique (Cnrs Agents de ciblage antitumoraux, leur preparation et applications
WO2007071028A1 (fr) * 2005-12-23 2007-06-28 St. Mary's University Composés, complexes et applications
JP2010524895A (ja) * 2007-04-18 2010-07-22 プロビオドルグ エージー グルタミニルシクラーゼ阻害剤としてのシアノグアニジン誘導体
CN104876936A (zh) * 2015-05-25 2015-09-02 中国人民解放军第二军医大学 吡咯酮并吡唑类化合物的制备及作为药物的用途
CN106749407A (zh) * 2017-01-06 2017-05-31 中国工程物理研究院核物理与化学研究所 一种氨基磷酸基功能化离子液体及其制备方法和用途
WO2019238786A1 (fr) * 2018-06-12 2019-12-19 Ryvu Therapeutics S.A. Modulateurs du stimulateur des gènes de l'interféron (sing)

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WO1988008840A1 (fr) * 1987-05-04 1988-11-17 Centre National De La Recherche Scientifique (Cnrs Agents de ciblage antitumoraux, leur preparation et applications
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