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US20030004296A1 - Latent curing agent for epoxy resin, and curable epoxy resin composition - Google Patents

Latent curing agent for epoxy resin, and curable epoxy resin composition Download PDF

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Publication number
US20030004296A1
US20030004296A1 US10/145,732 US14573202A US2003004296A1 US 20030004296 A1 US20030004296 A1 US 20030004296A1 US 14573202 A US14573202 A US 14573202A US 2003004296 A1 US2003004296 A1 US 2003004296A1
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US
United States
Prior art keywords
epoxy resin
polymer
curing agent
resin composition
molecule
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
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US10/145,732
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English (en)
Inventor
Hiroyasu Koto
Junji Ohashi
Hiroshi Sakamoto
Masato Kobayashi
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Ajinomoto Co Inc
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Ajinomoto Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ajinomoto Co Inc filed Critical Ajinomoto Co Inc
Assigned to AJINOMOTO CO., INC. reassignment AJINOMOTO CO., INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KOBAYASHI, MASATO, KOTO, HIROYASU, OHASHI, JUNJI, SAKAMOTO, HIROSHI
Publication of US20030004296A1 publication Critical patent/US20030004296A1/en
Priority to US11/110,731 priority Critical patent/US7226976B2/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • 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
    • 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

Definitions

  • the present invention relates to latent curing agents for epoxy resin, and to a curable epoxy resin compositions which contain such an agent. More precisely, the present invention relates to latent, epoxy resin-curing agents that exhibit good storage stability and low-temperature rapid curability of epoxy resin compositions containing it, and relates to curable epoxy resin compositions which contain such an agent and exhibit good storage stability and low-temperature rapid curability. The present invention further relates to methods for preparing articles by curing such an epoxy resin composition and the articles thereby obtained.
  • Epoxy resin compositions are used as the adhesive for electronic appliances, and they require a latent, epoxy resin-curing agent. However, it is much desired to further improve the quality of the curing agent. Needless-to-say, however, the applications of epoxy resins are not limited to the electronic industry.
  • Epoxy resin compositions are grouped into two types. One type is a two-package composition in which the main component epoxy resin and a curing agent are mixed just before use, and the other type is a one-package composition in which the main component epoxy resin is previously mixed with a curing agent. The latter one-package composition is preferred for the reason that it is free from the problems associated with incorrect mixing of the constituent components and it is applicable to automation lines driven by machine.
  • One-package epoxy resin compositions require a curing agent which does not react with an epoxy resin compound at room temperature but, when heated, starts to react with the epoxy compound to cure it. This type of curing agent is referred to as a latent curing agent.
  • Epoxy resin compositions containing a latent curing agent selected from a group consisting of dibasic acid dihydrazides and imidazoles can cure at relatively low temperatures, however their storage stability is not good. Boron trifluoride amine complexes are corrosive and have some negative influences on the properties of the cured products of epoxy resin compositions containing them. Under these circumstances, a latent curing agent for epoxy resin that produces epoxy resin compositions having good storage stability and low-temperature rapid curability is highly desired.
  • a curing agent of a dialkylamine adduct with an epoxy compound is proposed in Japanese Patent Laid-Open Nos. 155222/1981 and 100127/1982; and a curing agent of an aminoalcohol or an aminophenol adduct with an epoxy resin is proposed in Japanese Patent Laid-Open No. 53526/1984.
  • U.S. Pat. Nos. 4,066,625 and 4,268,656 disclose a curing agent of an imidazole compound or an N-methylpiperazine with an epoxy compound added to its secondary amino group.
  • Japanese Patent Laid-Open No. 296525/1991 discloses a one-package epoxy resin composition that contains a curing agent prepared through thermal reaction of an epoxide having more than one epoxy group on average in the molecule, an N,N-dialkylaminoalkylamine, a cyclic amine with an active hydrogen-containing nitrogen atom in the molecule, and a diisocyanate.
  • a curable epoxy resin composition prepared by mixing a latent curing agent for epoxy resin, which comprises two components of:
  • novel latent curing agents which comprise:
  • one component (A) of the curing agent of the present invention is a radically polymerized polymer of a monomer having at least one polymerizable double bond, and it has at least one tertiary amino group in the molecule.
  • various methods are applicable for introducing the at least one tertiary amino group into the molecule of the polymer.
  • an acrylate and/or methacrylate monomer may be used as a part of the monomer to be radically polymerized, and the resulting polymer may be reacted with an at least one tertiary amino group-containing alcohol compound for transesterification at the ester group in the polymer to introduce the tertiary amino group(s) into the polymer; or an acrylate and/or methacrylate monomer may be used as a part of the monomer to be radically polymerized, and the resulting polymer may be reacted with an at least one tertiary amino group-containing amine compound for ester-amide exchange at the ester group in the polymer to introduce the tertiary amino group(s) into the polymer; or a monomer having both at least one polymerizable double bond and at least one tertiary amino group in the molecule may be radically polymerized.
  • the acrylate compound to be used in the process that comprises transesterification or ester-amide exchange to introduce at least one tertiary amino group into the radically polymerized polymer may be, for example, methyl acrylate, isoamyl acrylate, 2-ethylhexyl acrylate, lauryl acrylate, benzyl acrylate, phenoxyethyl acrylate, isobomyl acrylate, or methoxydipropylene glycol acrylate; and the methacrylate compound to be used in the process may be, for example, methyl methacrylate, n-butyl methacrylate, i-butyl methacrylate, 2-ethylhexyl methacrylate, lauryl methacrylate, benzyl methacrylate, or cyclohexyl methacrylate.
  • the tertiary amino groups are a dialkylamino group such as a dimethylamino or die
  • Examples of the tertiary amino group-containing alcohol compounds for transesterification include 2-dimethylaminoethanol, 2-diethylaminoethanol, 1-(2-hydroxy-3-phenoxypropyl)-2-methylimidazole, 1-(2-hydroxy-3-butoxypropyl)-2-phenylimidazoline.
  • Examples of the tertiary amino group-containing amine compounds for ester-amide exchange include tertiary amino group-containing primary or secondary amine compounds such as dimethylaminopropylamine, diethylaminopropylamine, dimethyl aminoethylamine, N-aminoethylpiperazine, N,N-dimethylamino ethylpiperazine.
  • the tertiary amino group(s) in the radically polymerized polymer is preferably a dimethylamino group(s).
  • the produced polymer has the tertiary amino group(s).
  • the monomers having both at least one polymerizable double bond and at least one tertiary amino group in the molecule are 2-(N,N-dimethylamino)ethyl acrylate, 2-(N,N-dimethylamino) ethyl methacrylate, 2-(N,N-diethylamino)ethyl methacrylate, 3-(N,N-dimethylamino)propylacrylamide and the like.
  • radical polymerization of the polymerizable double bond-containing monomer in combination with the above mentioned acrylates, methacrylates, 2-(N,N-dimethylamino)ethyl acrylate, 3-(N,N-dimethylamino)propylacrylamide and others, one or more acrylamides such as N-isopropylacrylamide, acryloylmorpholine, or N,N-diethylacrylamide can be used.
  • the radical polymerization may be effected in any known manner, for example, the monomer system may be heated in the presence of a radical polymerization initiator such as a peroxide or a diazo compound.
  • any other radically-polymerizable monomer(s), for example, an olefin such as styrene, or an allyl compound such as allylamine, diallyl phthalate may be copolymerized into the polymer.
  • a polyfunctional acrylate and/or methacrylate such as 1,6-hexanediol diacrylate, neopentyl glycol diacrylate, trimethylolpropane triacrylate, ethylene glycol dimethacrylate, or trimethylolpropane trimethacrylate may also be copolymerized into the polymer.
  • the radical polymer, component (A) preferably has a softening point not higher than 150° C., more preferably not higher than 120° C.
  • the component (A) i.e. the radically polymerized polymer of at least one polymerizable double bond-containing monomer, which has at least one tertiary amino group in the molecule
  • the component (A) also contains at least one amido (—C( ⁇ O)NH 2 ) bond.
  • the polymer may be prepared by radically-polymerizing a monomer having both at least one tertiary amino group and at least one amido bond and also having at least one polymerizable double bond; or by polymerizing an acrylate and/or methacrylate monomer as a part of the monomer to be radically-polymerized, followed by reacting the resulting polymer with an at least one tertiary amino group-containing amine compound for amidation to introduce the tertiary amino group(s) and amido bond(s) into the polymer.
  • Examples of the monomer having both at least one tertiary amino group and at least one amido bond and also having at least one polymerizable double bond are acrylamide compounds having at least one tertiary amino group in the molecule, such as 3-(N,N-dimethylamino)propylacrylamide.
  • examples of the tertiary amino group-containing amine compounds are tertiary amino group-containing primary or secondary amine compounds such as dimethylaminopropylamine, diethylaminopropylamine, dimethylaminoethylamine, N-aminoethylpiperazine, and N,N-dimethylaminoethylpiperazine.
  • dimethylamino group-containing primary or secondary amine compounds such as dimethylaminopropylamine, N,N-dimethylaminoethylpiperazine.
  • the polymer having at least one hydroxyl group in the molecule which is component (B) of the curing agent of the present invention, is not specifically defined, so long as it has at least one hydroxyl group in the molecule and its mixture with the other component (A), the radically polymerized polymer of at least one polymerizable double bond-containing monomer, which has at least one tertiary amino group in the molecule, can be solid at 25° C.
  • the hydroxyl group may be either a phenolic hydroxyl group or an alcoholic hydroxyl group.
  • the hydroxyl group is preferably an alcoholic hydroxyl group.
  • the component (B), the polymer having at least one hydroxyl group in the molecule may be, for example, radically polymerized polymers of acrylates having at least one hydroxyl group in the molecule and/or methacrylates having at least one hydroxyl group in the molecule; radically-polymerized polymers of polyhydric alcohols such as polyvinyl alcohol, polyvinyl butyral; polymers of polyphenols; condensates of polyhydric alcohols and polycarboxylic acids; phenoxy resins obtained through reaction of a phenolic compound such as bisphenol A or bisphenol S with epichlorohydrin; and polyadducts of epoxy resins and active hydrogen compounds.
  • Examples of the acrylates having at least one hydroxyl group in the molecule and the methacrylates having at least one hydroxyl group in the molecule are 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, bisphenol A diglycidyl ether/methacrylic acid adduct, and pentaerythritol triacrylate.
  • polymers of polyphenols are, for example, radically polymerized polymers of polyphenols such as para-vinylphenol polymers obtained through polymerizing p-hydroxystyrene; and phenol-novolak resins and resol resins obtained through polycondensation of a phenolic compound such as phenol, cresol, catechol, bisphenol A, bisphenol S, resorcinol, tetrabromobisphenol A or biphenyl, with formalin.
  • a phenolic compound such as phenol, cresol, catechol, bisphenol A, bisphenol S, resorcinol, tetrabromobisphenol A or biphenyl, with formalin.
  • Examples of the condensates of polycarboxylic acid compounds and polyhydric alcohol compounds are polycondensates of adipic acid and pentaerythritol and the like.
  • the epoxy resin to be reacted with an active hydrogen compound to produce a polyaddition product thereof is a compound having at least two epoxy groups in the molecule.
  • it includes glycidyl ethers obtained through reaction of a polyphenol such as bisphenol A, bisphenol F, bisphenol S, hexahydrobisphenol A, tetramethylbisphenol A, hydroquinone, catechol, resorcinol, cresol, tetrabromobisphenol A, trihydroxybiphenyl, benzophenone, bisresorcinol, bisphenol-hexafluoroacetone, tetramethylbisphenol A, tetramethylbisphenol F, tris(hydroxyphenyl)methane, bixylenol, phenol-novolak or cresol-novolak, with epichlorohydrin; polyglycidyl ethers obtained through reaction of an aliphatic polyhydric alcohol such as glycerin, neopent
  • the active hydrogen compound is a compound having, in the molecule, at least two active hydrogen atoms capable of reacting with epoxy groups.
  • the compound has a functional group selected from an amino group, a phenolic hydroxyl group, an alcoholic hydroxyl group, a mercapto group, a carboxyl group and a hydrazido group, and has at least two active hydrogen atoms of the group in the molecule.
  • amine compounds for example, aliphatic amine compounds such as cyclohexylamine, piperazine, metaxylylenediamine, 1,3-bis (aminomethyl)cyclohexane, isophoronediamine, diamino cyclohexane, 3,9-bis(3-aminopropyl)-2,4,8,10-tetroxaspiro [5,5]undecane; tertiary amino group-containing aliphatic primary amine compounds such as dimethylaminopropylamine, diethylaminopropylamine, dimethylaminoethylamine, N-amino ethylpiperazine; aromatic amine compounds such as phenylene diamine, toluylenediamine, diaminodiphenylmethane, diamino diphenyl sulfone; as well as polyphenol compounds such as bisphenol A, bisphenol F, bisphenol S, hexahydrobis
  • a monofunctional glycidyl ether compound such as butyl glycidyl ether or phenyl glycidyl ether
  • a monofunctional glycidyl ester compound such as glycidyl benzoate
  • a monoepoxy compound such as styrene oxide
  • the polymer of the component (B) having at least one hydroxyl group in the molecule may be copolymerized with a compound not having a hydroxyl group in the molecule.
  • the polymer of the component (B) may contain both an alcoholic hydroxyl group(s) and a phenolic hydroxyl group(s).
  • the polymer of the component (B) having at least one hydroxyl group in the molecule is preferably solid at 25° C.
  • the polymer of the component (B) is more preferably a reaction product of an epoxy resin and an active hydrogen compound.
  • the polymer of the component (B) having at least one hydroxyl group in the molecule has a urethane (—OC( ⁇ O)NH 2 ) and/or urea (—NHC( ⁇ O)NH 2 ) bond(s) in the molecule.
  • Urethane and/or urea bond(s) may be introduced into the polymer molecule, for example, by reacting the polymer having at least one hydroxyl group in the molecule with an isocyanate compound; or by reacting an epoxy resin with an active hydrogen compound and with an isocyanate compound.
  • the isocyanate compound includes, for example, monoisocyanate compounds such as phenyl isocyanate, octadecyl isocyanate; diisocyanate compounds such as isophorone diisocyanate, metaxylylene diisocyanate, 1,3-bis (isocyanatomethyl)cyclohexane, 2,4-toluylene diisocyanate, 2,6-toluylene diisocyanate, 1,6-hexane diisocyanate, 1,5-naphthalene diisocyanate, 1,4-phenylene diisocyanate, diphenylmethane diisocyanate, which may be in any form of their isomer mixtures; carbodiimide-modified derivatives and biuret-modified derivatives of such isocyanate compounds; and isocyanate prepolymers through reaction of isocyanate compounds and polyol compounds, such as a reaction product of 2,4-toluylene diiso
  • the softening point of the polymer of the component (B) having at least one hydroxyl group in the molecule is not higher than 150° C., more preferably not higher than 120° C. If the softening point of the polymer of the component (B) is higher than 150° C., the low-temperature curability of the epoxy resin composition will be extremely reduced.
  • the latent curing agent for epoxy resin of the present invention comprises a solid solution containing the two components (A) and (B). Even though the components have a low softening point and are therefore difficult to grind individually, their solid solution can be readily ground into fine powder and can be uniformly dispersed in an epoxy resin composition. Even if the component (A) alone can be ground and added to an epoxy resin composition, the resulting mixture could not be uniformly cured since the component (A) is poorly miscible with the epoxy resin composition. When the component (A) is combined with the component (B) and forms a solid solution, the solid solution is well miscible with an epoxy resin composition and the epoxy resin composition containing the solid solution can be uniformly cured. On the other hand, the component (B), if added alone to an epoxy resin composition, could not improve both the low-temperature curability and the storage stability of the epoxy resin composition.
  • a solvent may be used or not, depending on the properties of the starting compounds to be reacted.
  • the solvent is not specifically defined and may be any conventional one. However, if too much solvent remains in the solid solution of components (A) and (B), the properties of the cured product of the epoxy resin composition will be lowered. Therefore, solvents with high-boiling-point are unfavorable.
  • the solvent may be water; alcohols such as methanol, ethanol, isopropanol; ketones such as acetone, methyl ethyl ketone; esters such as ethyl acetate; and aromatic hydrocarbons such as toluene, xylene.
  • the components (A) and (B) may be separately prepared, and may be dissolved in a solvent that dissolves the two, and the solvent may be removed from the resulting solution; or the two components may be heated up to a temperature at which they melt, and then kneaded in melt; or any one of the two components may be first prepared, and the other component may be produced in the presence of the previously-prepared component.
  • suitable methods are selected for producing the solid solution.
  • the ratio of the component (A) to the component (B), i.e. (A)/(B), can be between 1/20 and 3/1 by weight. If the ratio of the component (A) is smaller than 1/20, the low-temperature curability of the epoxy resin composition containing the curing agent will be poor, and the composition will fail to attain the advantages of the present invention. On the other hand, if the ratio of the component (A) is larger than 3/1, the storage stability of the epoxy resin composition will be poor.
  • the solid solution of the invention may be solid at 25° C. If not solid at 25° C., the solid solution will be extremely difficult to be ground, and even if ground, it might not be stored and handled at room temperature and can not be mixed to an epoxy resin composition.
  • the softening point of the solid solution falls between 40° C. and 150° C. If the softening point thereof is lower than 40° C., the storage stability of the epoxy resin composition containing the curing agent will be poor; but if higher than 150° C., the low-temperature curability of the resin composition will be poor.
  • the solid solution of the present invention may contain any other component(s) not adversely affecting the advantages of the present invention.
  • conventional compounds known as a curing agent or a cure accelerator for epoxy resin such as imidazole compounds including 2-methylimidazole, 1,2-dimethylimidazole, 1-benzyl-2-phenylimidazole, 1-(2-hydroxy-3-phenoxypropyl)-2-methylimidazole; tertiary amine compounds including 2,4,6-tris(dimethylaminomethyl) phenol; phosphine compounds including triphenyl phosphine, may be added in the solid solution, so far as not adversely affecting the advantages of the present invention.
  • the solvent and the catalyst used in producing the components (A) and (B) as well as the non-reacted compounds remaining in the produced components may also exist in the solid solution, so far as not adversely affecting the advantages of the invention.
  • the solid solution comprised in the curing agent of the present invention is generally ground into particles having a desired particle size for use.
  • the particle size thereof may be from 0.03 ⁇ m to 300 ⁇ m.
  • the latent curing agent for epoxy resin of the present invention may further contain, if desired, any known curing agent of, for example, dicyandiamides, hydrazide compounds, guanamine compounds or phenol-novolak resins, as well as other additives such as surface-treating agents, inorganic fillers and pigments.
  • the invention provides curable epoxy resin compositions, which comprises an epoxy compound having at least two epoxy groups in the molecule and the latent curing agent for epoxy resin of the present invention.
  • the epoxy resin may be a compound having at least two epoxy groups in the molecule. It includes all known epoxy resins, for example, glycidyl ethers obtained through reaction of polyphenols, such as bisphenol A, bisphenol F, bisphenol S, hexahydrobisphenol A, tetramethylbisphenol A, diallylbisphenol A, hydroquinone, catechol, resorcinol, cresol, tetrabromo bisphenol A, trihydroxybiphenyl, benzophenone, bisresorcinol, bisphenol-hexafluoroacetone, tetramethylbisphenol A, tetramethylbisphenol F, tris(hydroxyphenyl)methane, bixylenol, phenol-novolak or cresol-novolak, with epichlorohydrin; polyglycidyl ethers obtained through reaction of aliphatic polyhydric alcohols, such as glycerin, neopentyl glycol,
  • the amount of the latent curing agent for epoxy resin of the present invention to be used in the epoxy resin composition of the present invention may be from 0.3 to 50 parts by weight relating to 100 parts by weight of the epoxy compound in the composition. If the amount of the curing agent therein is smaller than 0.3 parts by weight, the resin composition could not cure sufficiently; on the other hand, if larger than 50 parts by weight, it will adversely affect the properties of the cured product of the resin composition. However, in case where the latent curing agent for epoxy resin of the present invention is used as a cure accelerator for known curing agents, the amount thereof should not be limited to that range.
  • the epoxy resin composition of the present invention may contain any other known curing agent(s) of, for example, phenolic compounds, acid anhydrides, dicyandiamides, hydrazide compounds, thiol compounds, guanamines or melamines, as well as a cure accelerator(s) of, for example, imidazole compounds or tertiary amines, in addition to the latent curing agent of the invention.
  • the epoxy resin composition may contain any other additives.
  • additives examples include inorganic fillers such as alumina, silica, calcium carbonate, aluminium hydroxide, magnesium hydroxide, talc, bentonite, barium carbonate, and Aerosil; viscosity adjusters such as acrylic oligomers, silicones; coupling agents such as silane-coupling agents; flame retardants such as phosphates, phosphorus-containing epoxy compounds, and nitrogen-containing phenolic resins; fillers such as nylon particles, polystyrene particles, crosslinked rubber particles, acrylic core/shell particles, rubber-type core/shell particles, silicone particles, and ethylene-acrylic acid copolymer particles; resin modifiers such as carboxyl-terminated, liquid acrylic oligomers; and pigments.
  • inorganic fillers such as alumina, silica, calcium carbonate, aluminium hydroxide, magnesium hydroxide, talc, bentonite, barium carbonate, and Aerosil
  • viscosity adjusters such as acrylic oligomers, silicones
  • the present invention provides a method for preparing an article, said method comprising:
  • said epoxy resin composition comprises:
  • said latent curing agent comprises:
  • the latent curing agent and the epoxy resin composition are as described above.
  • the substrate may be of any material conventionally bonded or coated with epoxy resin compositions, including metals, such as steel, copper, bronze, gold, silver, platinum, etc., or a plastic, such as polystyrene, polyamide, polyimide, etc.
  • the article may be any article of manufacture which is conventionally prepared by curing an epoxy resin composition, including electronic devices, such as telephone, computers, electronic games, televisions, audio components, etc.
  • the present epoxy resin composition may be applied to the surface of the substrate manually or by machine in an automated process. The optimum amount of epoxy resin applied will, of course depend on the exact nature of the substrate and article.
  • the present epoxy resin compositions are generally used in amounts similar to those used for conventional one-part epoxy resin compositions.
  • the epoxy resin composition may be cured by the application of heat.
  • the optimum temperature and time of the curing step will vary with the exact composition of the epoxy resin composition but may be easily determined on a case-by-case basis.
  • the epoxy resin composition of the present invention has improved low-temperature curability and storage stability than conventional ones. Therefore, when used for adhesives, coating materials, sealants, molding materials and composites, its workability is excellent. In addition, since the resin composition rapidly cures even at such low temperatures of 60° C. to 70° C., it is favorable for bonding structures of low heat resistant materials like plastics to which conventional one-package epoxy resin adhesives are not applicable. Further, the resin composition is applicable even in bonding parts of minute instruments that require high dimensional accuracy and in bonding parts of electronic devices sensitive to heat, to which conventional one-package epoxy resin adhesives are not applicable. Still further, since the resin composition rapidly cures even at low temperatures, the energy for curing such adhesives may be reduced. As stated in the above, the epoxy resin composition that contains the curing agent of the present invention has remarkable industrial advantages.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)
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Cited By (3)

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US20050149788A1 (en) * 2003-12-23 2005-07-07 Ki-Seok Jeon Methods of testing semiconductor memory devices in a variable CAS latency environment and related semiconductor test devices
US20080114124A1 (en) * 2004-12-22 2008-05-15 Riaz Ahmad Choudhery Aqueous Polymer Dispersions
WO2020019278A1 (en) * 2018-07-27 2020-01-30 Henkel Ag & Co. Kgaa Two-part epoxy based composition

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US7226976B2 (en) 2007-06-05
EP1260532A1 (en) 2002-11-27
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TWI242020B (en) 2005-10-21

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