US20130136930A1 - Resin composition, prepreg, and laminate - Google Patents

Resin composition, prepreg, and laminate Download PDF

Info

Publication number
US20130136930A1
US20130136930A1 US13/816,008 US201113816008A US2013136930A1 US 20130136930 A1 US20130136930 A1 US 20130136930A1 US 201113816008 A US201113816008 A US 201113816008A US 2013136930 A1 US2013136930 A1 US 2013136930A1
Authority
US
United States
Prior art keywords
weight
parts
resin
resin composition
composition according
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
Application number
US13/816,008
Other languages
English (en)
Inventor
Yoshihiro Kato
Takaaki Ogashiwa
Hiroshi Takahashi
Tetsuro Miyahira
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Gas Chemical Co Inc
Original Assignee
Mitsubishi Gas Chemical 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 Mitsubishi Gas Chemical Co Inc filed Critical Mitsubishi Gas Chemical Co Inc
Assigned to MITSUBISHI GAS CHEMICAL COMPANY, INC. reassignment MITSUBISHI GAS CHEMICAL COMPANY, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KATO, YOSHIHIRO, OGASHIWA, TAKAAKI, MIYAHIRA, TETSURO, TAKAHASHI, HIROSHI
Publication of US20130136930A1 publication Critical patent/US20130136930A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C08K3/0083—
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H05K1/0313—Organic insulating material
    • H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
    • H05K1/0373—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B32B15/092—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising epoxy resins
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/22—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed
    • B32B5/24—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer
    • B32B5/26—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer another layer next to it also being fibrous or filamentary
    • 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
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4014—Nitrogen containing compounds
    • 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
    • C08G59/62—Alcohols or phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
    • C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/10—Metal compounds
    • C08K3/105—Compounds containing metals of Groups 1 to 3 or of Groups 11 to 13 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • C08K3/26—Carbonates; Bicarbonates
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08K9/00—Use of pretreated ingredients
    • C08K9/02—Ingredients treated with inorganic substances
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
    • B32B2260/04—Impregnation, embedding, or binder material
    • B32B2260/046—Synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
    • B32B2262/10—Inorganic fibres
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/30—Properties of the layers or laminate having particular thermal properties
    • B32B2307/306—Resistant to heat
    • B32B2307/3065—Flame resistant or retardant, fire resistant or retardant
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/50—Properties of the layers or laminate having particular mechanical properties
    • B32B2307/58—Cuttability
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/70—Other properties
    • B32B2307/732—Dimensional properties
    • B32B2307/734—Dimensional stability
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2457/00—Electrical equipment
    • B32B2457/08—PCBs, i.e. printed circuit boards
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • C08J2363/04—Epoxynovolacs
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • C08K3/26—Carbonates; Bicarbonates
    • C08K2003/262—Alkali metal carbonates
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • C08K3/26—Carbonates; Bicarbonates
    • C08K2003/267—Magnesium carbonate
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/002—Physical properties
    • C08K2201/003—Additives being defined by their diameter
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/02—Flame or fire retardant/resistant
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/08—Stabilised against heat, light or radiation or oxydation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/22—Halogen free composition
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
    • H05K2201/01—Dielectrics
    • H05K2201/0104—Properties and characteristics in general
    • H05K2201/012—Flame-retardant; Preventing of inflammation
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
    • H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
    • H05K2201/0203—Fillers and particles
    • H05K2201/0206—Materials
    • H05K2201/0209—Inorganic, non-metallic particles
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31511—Of epoxy ether
    • Y10T428/31529—Next to metal

Definitions

  • the present invention relates to a resin composition and more particularly relates to a resin composition for use in prepregs for printed wiring boards.
  • the present invention also relates to a prepreg for printed wiring boards prepared using the resin composition, and a laminated sheet and a metal foil-clad laminated sheet prepared using the prepreg.
  • metal hydrates are known as halogen-free flame retardants as an alternative to bromine-containing flame retardants.
  • aluminum hydroxide is known as a flame retardant that, when heated, causes a reaction that releases water of crystallization.
  • gibbsite that is a general structure of aluminum hydroxide
  • heat resistance is deteriorated due to an influence of water of crystallization that is released upon heating.
  • boehmite obtained by hydrothermally treating aluminum hydroxide is also known (see, for example, patent document 1).
  • Copper-clad laminated sheets prepared using boehmite are superior in heat resistance to those prepared using aluminum hydroxide, but on the other hand, drilling workability and coefficient of thermal expansion in a plane direction are unsatisfactory.
  • a mixture composed of hydromagnesite and huntite is known to improve flame retardance.
  • thermoplastic resins such as polyolefin resins
  • the resin is not used for laminated sheet applications.
  • a method in which an inorganic filler or an organic filler is filled into resins is known to reduce the coefficient of thermal expansion in a plane direction of laminated sheets (see, for example, patent document 3).
  • This method suffers from a problem that increasing the amount of the inorganic filler filled into the resins to further lower the coefficient of thermal expansion is disadvantageous in that the resultant resin composition is hard and fragile, the abrasion of drill bits is fast, and breakage of drill bits and a lowering in the accuracy of hole position lead to an increased frequency of replacement of drill bits, resulting in a deteriorated drilling workability.
  • An object of the present invention is to provide a resin composition for printed wiring boards that has a low coefficient of thermal expansion in a plane direction, has high heat resistance and drilling workability, and can retain a high level of flame retardance, a prepreg prepared using the resin composition, and a laminated sheet and a metal foil-clad laminated sheet prepared using the prepreg.
  • a prepreg comprising a base material impregnated or coated with a resin composition comprising an inorganic filler (A) that is a mixture composed of hydromagnesite and huntite, an epoxy resin (B), and a curing agent (C) can provide a laminated sheet that has a low coefficient of thermal expansion in a plane direction relative to the amount of the inorganic filler, has high heat resistance and drilling workability, and can retain a high level of flame retardance.
  • the present invention has been made based on such finding.
  • a resin composition comprising:
  • x:y:z is 4:1:4, 4:1:5, 4:1:6, 4:1:7, 3:1:3, or 3:1:4 and huntite;
  • a prepreg comprising: a base material; and the resin composition impregnated into or coated on the base material.
  • a laminated sheet comprising a lamination-molded product of the prepreg.
  • a metal foil-clad laminated sheet comprising a lamination-molded product of the prepreg and a metal foil provided on the prepreg.
  • the laminated sheet obtained from the prepreg comprising the resin composition according to the present invention impregnated into or coated on a based material has an excellent heat resistance, has a high level of flame retardance without the need to use a halogen compound or a phosphorus compound, has an excellent drilling workability, and has a low coefficient of thermal expansion in a plane direction relative to the amount of an inorganic filler and thus is usable as materials for semiconductor packages of which various properties are required.
  • the resin composition according to the present invention comprises: an inorganic filler (A) that is a mixture composed of hydromagnesite and huntite; an epoxy resin (B); and a curing agent (C).
  • the resin composition may comprise other ingredients such as a maleimide compound and a silicone powder. The individual ingredients constituting the resin composition will be described.
  • the inorganic filler (A) used in the present invention is formed of fine particles obtained by grinding a mineral that is a homogeneous mixture of two ingredients that are naturally occurring hydromagnesite and huntite.
  • the hydromagnesite has a structure represented by formula (1):
  • x:y:z is 4:1:4, 4:1:5, 4:1:6, 4:1:7, 3:1:3, or 3:1:4.
  • the hydromagnesite particularly preferably has a structure of 4MgCO 3 .Mg(OH) 2 .4H 2 O from the viewpoint of a flame retarding effect.
  • the huntite has a structure represented by formula (2):
  • the inorganic filler (A) has a particle diameter of 0.2 to 100 ⁇ m.
  • This inorganic filler (A) may be of a commonly commercially available industrial grade. Examples thereof include Ultracarb1200 manufactured by Minelco and Hypercarb2050 manufactured by Minelco.
  • the amount of the inorganic filler (A) incorporated is preferably approximately 5 to 250 parts by weight, more preferably 30 to 200 parts by weight, particularly preferably 60 to 150 parts by weight, based on 100 parts by weight in total of the epoxy resin (B) and the curing agent (C).
  • the amount of the inorganic filler (A) incorporated is not less than 5 parts by weight, a flame retarding effect of the inorganic filler (A) is obtained.
  • the amount of the inorganic filler (A) incorporated is not more than 250 parts by weight, the drilling workability is good.
  • the inorganic filler used in the present invention may also be a combination of the mixture composed of hydromagnesite and huntite with inorganic fillers other than the mixture composed of hydromagnesite and huntite.
  • Any inorganic filler commonly used for printed wiring materials may be used without particular limitation as the inorganic filler that may be combined with the inorganic filler that is a mixture composed of hydromagnesite and huntite.
  • Examples thereof include silicas such as naturally occurring silica, fused silica, amorphous silica, and hollow silica, molybdenum compounds such as boehmite, molybdenum oxide, and zinc molybdate, alumina, talc, calcined talc, mica, glass short fibers, and spherical glass (for example finely divided glass such as E-glass, T-glass, D-glass, S-glass, and Q-glass).
  • silicas such as naturally occurring silica, fused silica, amorphous silica, and hollow silica
  • molybdenum compounds such as boehmite, molybdenum oxide, and zinc molybdate
  • alumina talc
  • calcined talc mica
  • glass short fibers glass short fibers
  • spherical glass for example finely divided glass such as E-glass, T-glass, D-glass, S-glass, and Q-glass.
  • the indispensable ingredients may also be used in combination with silane coupling agents and wetting/dispersing agents.
  • silane coupling agents or wetting/dispersing agents can contribute to improved dispersibility of the inorganic filler.
  • Any silane coupling agent commonly used in surface treatment of inorganic materials may be used without particular limitation.
  • aminosilane coupling agents such as ⁇ -aminopropyltriethoxysilane and N- ⁇ -(aminoethyl)- ⁇ -aminopropyltrimethoxysilane
  • epoxysilane coupling agents such as ⁇ -glycidoxypropyltrimethoxysilane
  • vinylsilane coupling agents such as ⁇ -methacryloxypropyltrimethoxysilane
  • cationic silane coupling agents such as N- ⁇ -(N-vinylbenzylaminoethyl)- ⁇ -aminopropyltrimethoxysilane hydrochloride, and phenylsilane coupling agents.
  • the coupling agents may be used solely or in a proper combination of two or more of them.
  • Any dispersion stabilizer commonly used for coating materials may be used as the wetting/dispersing agent without particular limitation. Examples thereof include wetting/dispersing agents such as Disperbyk-110, Disperbyk-111, Disperbyk-180, Disperbyk-161, BYK-W996, BYK-W9010, and BYK-W903 manufactured by BYK Japan K.K.
  • any epoxy resin commonly used as materials for printing wiring boards may be used as the epoxy resin (B) used in the present invention without particular limitation.
  • Typical preferred examples of the epoxy resin (B) are non-halogn epoxy resins from the viewpoint of a growing concern about environmental problems. Examples thereof include bisphenol A epoxy resins, bisphenol F epoxy resins, phenol novolak epoxy resins, cresol novolak epoxy resins, bisphenol A novolak epoxy resins, trifunctional phenolic epoxy resins, tetrafunctional phenolic epoxy resins, naphthalene epoxy resins, biphenol epoxy resins, aralkyl novolak epoxy resins, alicyclic epoxy resins, polyol epoxy resins, compounds obtained by epoxidizing a double bond, for example, in glycidylamines, glycidyl esters, and butadiene, and compounds obtained by reacting hydroxyl-containing silicone resins with epichlorohydrin.
  • phenol novolak epoxy resins and aralkyl novolak epoxy resins are preferred from the viewpoint of improving flame retardance and heat resistance, and aralkyl novolak epoxy resins represented by formula (3) are more preferred from the viewpoint of further improving flame retardance.
  • Aralkyl novolak epoxy resins include phenol phenyl aralkyl epoxy resins, phenol biphenyl aralkyl epoxy resins, and naphthol aralkyl epoxy resins. Phenol phenyl aralkyl epoxy resins represented by formula (4) are particularly preferred. The use of one of or a proper combination of two or more of them may also be possible depending upon contemplated purposes.
  • Ar 1 s which may be the same or different, represent and Ar 2 represents or when present in plural which may be the same or different, represent an aryl group in which the substituent is a monocyclic or polycyclic aromatic hydrocarbon of a phenyl, naphthyl, or biphenyl group
  • Rxs which may be the same or different, represent and Ry represents or when present in plural which may be the same or different, represent a hydrogen atom or an alkyl or aryl group
  • m is an integer of 1 to 5
  • n is an integer of 1 to 50
  • G represents a glycidyl group.
  • n is an integer of 1 or more.
  • the amount of the epoxy resin (B) is preferably approximately 5 to 70 parts by weight, particularly preferably approximately 10 to 40 parts by weight, based on 100 parts in total of the epoxy resin (B) and the curing agent (C).
  • the amount of the epoxy resin (B) is not less than 5 parts by weight, a contemplated cured product can be obtained while, when the amount of the epoxy resin (B) is not more than 70 parts by weight, good heat resistance can be obtained.
  • the curing agent (C) used in the present invention is not particularly limited as long as commonly used epoxy resins are curable.
  • examples thereof include cyanate ester compounds and BT resins (bismaleimide triazine resins) that are excellent in heat resistance, particularly in electrical characteristics such as permittivity and dielectric loss tangent, and phenolic resins that have low water absorption and high heat resistance. They may be used solely or in a proper combination of two or more of them.
  • cyanate ester compounds may be used as the cyanate ester compound.
  • Examples thereof include naphthol aralkyl cyanate ester compounds represented by formula (5), 1,3-dicyanatobenzene, 1,4-dicyanatobenzene, 1,3,5-tricyanatobenzene, bis(3,5-dimethyl-4-cyanatophenyl)methane 1,3-dicyanatonaphthalene, 1,4-dicyanatonaphthalene, 1,6-dicyanatonaphthalene, 1,8-dicyanatonaphthalene, 2,6-dicyanatonaphthalene, 2,7-dicyanatonaphthalene, 1,3,6-tricyanatonaphthalene, 4,4′-dicyanatobiphenyl, bis(4-cyanatophenyl)methane, 2,2′-bis(4-cyanatophenyl)propane, bis(4-cyanatophenyl)ether, bis(4-cyanatophenyl)thioether
  • R 11 represents a hydrogen atom or a methyl group
  • q is an integer of 1 or more.
  • Any BT resin that is composed mainly of a maleimide compound and a cyanate ester compound and has been prepolymerized may be used as the BT resin without particular limitation.
  • Examples thereof include products obtained by heat-melting 2,2-bis(4-cyanatophenyl)propane (CX, manufactured by Mitsubishi Gas Chemical Co., Inc.) and bis(3-ethyl-5-methyl-4-maleimidiphenyl)methane (BMI-70, manufactured by K.I.
  • BT resins containing naphthol aralkyl cyanate ester compounds can maintain heat resistance by virtue of a resin skeleton having a rigid structure and can reduce a reaction inhibition factor to enhance curability and thus to realize excellent water absorption and heat resistance and thus are suitable for use by virtue of these properties.
  • One type of or a proper mixture of two or more of cyanate ester compounds that are raw materials for BT resins may be used.
  • any resins having two or more phenolic hydroxyl groups per molecule may be used as the phenolic resin without particular limitation.
  • Examples thereof include naphthol aralkyl phenolic resins represented by formula (6), phenol novolak resins, alkyl phenol novolak resins, bisphenol A novolak resins, dicyclopentadiene phenolic resins, xylok phenolic resins, terpene-modified phenolic resins, polyvinyl phenols, naphthol aralkyl phenolic resins, biphenyl aralkyl phenolic resins, naphthalene phenolic resins, and aminotriazine novolak phenolic resins.
  • At least one resin selected from the group consisting of naphthol aralkyl phenolic resins, biphenyl aralkyl phenolic resins, and naphthalene phenolic resins is preferred from the viewpoints of water absorption and heat resistance, and naphthol aralkyl phenolic resins represented by formula (6) are more preferred from the viewpoint of further improving water absorption.
  • R represents a hydrogen atom or a methyl group
  • n is an integer of 1 or more.
  • the phenolic resin is incorporated so that the ratio of the number of hydroxyl groups in the phenolic resin to the number of glycidyl groups in the epoxy resin is preferably 0.7 to 2.5.
  • the ratio of the number of hydroxyl groups in the phenolic resin to the number of glycidyl groups in the epoxy resin is preferably not less than 0.7 from the viewpoint of preventing a lowering in glass transition temperature and is preferably not more than 2.5 from the viewpoint of preventing a lowering in flame retardance.
  • the phenolic resin may also be used in combination with BT resins obtained by prepolymerizing a cyanate ester compound or a combination of a cyanate ester compound with a maleimde compound.
  • the resin composition according to the present invention may further comprise a maleimide compound.
  • the maleimide compound has the effect of improving heat resistance.
  • Any maleimide compound containing one or more maleimide groups per molecule may be used as the maleimide compound in the present invention.
  • Specific examples thereof include N-phenylmaleimide, N-hydroxyphenylmaleimide, bis(4-maleimidephenyl)methane, 2,2-bis ⁇ 4-(4-maleimidephenoxy)-phenyl ⁇ propane, bis(3,5-dimethyl-4-maleimidephenyl)methane, bis(3-ethyl-5-methyl-4-maleimidephenyl)methane, bis(3,5-d iethyl-4-maleimidephenyl)methane, polyphenyl methane maleimide, prepolymers of these maleimide compounds, or prepolymers of a combination of maleimide compounds with amine compounds.
  • Bis(4-maleimidephenyl)methane, 2,2-bis ⁇ 4-(4-maleimidephenoxy)-phenyl ⁇ propane, and bis(3-ethyl-5-methyl-4-maleimidephenyl)methane are more suitable.
  • the amount of the maleimide compound used is preferably approximately 3 to 50 parts by weight, particularly preferably 5 to 30 parts by weight, based on 100 parts by weight in total of the epoxy resin (B), the curing agent (C), and the maleimide compound.
  • the resin composition according to the present invention may further comprise a silicone powder.
  • the silicone powder functions as an auxiliary flame retardants that delay a combustion time and enhance a flame retarding effect. Further, the silicone powder has the effect of enhancing drilling workability.
  • examples of such silicone powders include products obtained by finely dividing a polymethyl silsesquioxane to which siloxane bonds are crosslinked in a three-dimensional network form, products obtained by finely dividing an addition polymerization product of a vinyl group-containing dimethylpolysiloxane and a methylhydrogenpolysiloxane, products obtained by covering the surface of a fine powder of an addition polymerization product of a vinyl group-containing dimethylpolysiloxane and a methylhydrogenpolysiloxane with a polymethylsilsesquioxane to which siloxane bonds are crosslinked in a three-dimensional network form, and products obtained by covering the surface of an inorganic support with a polymethylsilsesquiox
  • the average particle diameter (D50) of the silicone powder is not particularly limited. Preferably, however, the average particle diameter (D50) is 1 to 15 ⁇ m from the viewpoint of dispersibility.
  • D50 means a median diameter which is a diameter that, when a measured particle size distribution of the powder is divided into two groups, the amount of particles on a coarser side is equal to the amount of particles on a finer side.
  • the D50 value is generally measured by a wet laser diffraction-scattering method.
  • the amount of the silicone powder incorporated is not particularly limited but is preferably 1 to 30 parts by weight, particularly preferably 2 to 20 parts by weight, based on 100 parts by weight in total of the epoxy resin (B) and the curing agent (C).
  • the amount of the silicone powder incorporated is preferably not less than 1 part by weight from the viewpoint of improving drilling workability and is preferably not more than 30 parts by weight from the viewpoint of preventing a lowering in moldability and dispersibility.
  • the resin composition according to the present invention may if necessary additionally contain curing accelerators for properly regulating the curing speed.
  • Any curing accelerators commonly used in curing epoxy resins, cyanate ester compounds, and phenolic resins may be used without particular limitation. Specific examples thereof include organic metal salts and imidazole compounds of copper, zinc, cobalt, nickel and the like and their derivatives, and tertiary amines. They may be used solely or in a proper combination of two or more of them.
  • the resin composition according to the present invention may additionally contain various polymer compounds such as other heat curable resins, thermoplastic resins, and oligomers and elastomers thereof, other flame retarding compounds, and additives in such an amount that does not sacrifice desired properties. They may be generally used without particular limitation as long as they are commonly used in resin compositions for printed wiring boards. Examples of flame retarding compounds include nitrogen-containing compounds such as melamine and benzoguanamine and oxazine ring-containing compounds.
  • Additives include, for example, ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent brighteners, photosensitizers, dyes, pigments, thickeners, lubricants, antifoaming agents, dispersants, leveling agents, brighteners, and polymerization inhibitors. These additives may be used in a proper combination according to need.
  • the resin composition according to the present invention may be produced by any process without particular limitation as long as the inorganic filler (A), the epoxy resin (B), and the curing agent (C) are combined to obtain the resin composition.
  • Examples of production processes include a process that comprises incorporating the inorganic filler (A) into the epoxy resin (B), dispersing the ingredients in each other with a homomixer or the like, and incorporating the curing agent (C) into the dispersion.
  • an organic solvent is added from the viewpoints of lowering viscosity, improving handleability, and enhancing a capability of being impregnated into glass clothes.
  • the prepreg according to the present invention comprises the resin composition impregnated into or coated on a base material.
  • base materials used in various materials for printed wiring boards may be used as the base materials used in the production of the prepreg according to the present invention. Examples thereof include glass fibers such as E-glass, D-glass, S-glass, NE-glass, T-glass, Q-glass, and spherical glass fibers, inorganic fibers other than the glass fibers, or organic fibers such as polyimide, polyamide, and polyester fibers.
  • These base materials may be properly selected depending upon contemplated applications and properties.
  • Examples of the form of the base material include woven fabrics, nonwoven fabrics, rovings, chopped strand mats, and surfacing mats.
  • the thickness of the base material is not particularly limited but is generally approximately 0.01 to 0.3 mm.
  • E-glass fibers are particularly preferred from the viewpoint of a balance between the coefficient of thermal expansion in a plane direction and the drilling workability.
  • the prepreg according to the present invention may be produced by any process without particular limitation as long as a prepreg comprising a combination of the resin composition comprising the inorganic filler (A), the epoxy resin (B), and the curing agent (C) with the base material can be obtained.
  • the prepreg may be produced by impregnating or coating the base material with a resin varnish comprising the resin composition and an organic solvent and heating the impregnated or coated base material in a drier of 100 to 200° C. for 1 to 60 min to semi-cure the resin.
  • the amount of the resin composition (including the inorganic filler) deposited on the base material is preferably in the range of 20 to 90% by weight based on the whole prepreg.
  • the organic solvent is used to lower the viscosity of the resin composition, improve the handleability, and, at the same time, enhance impregnation of the resin composition into the glass cloth.
  • Any organic solvent may be used in the resin varnish without particular limitation as long as the epoxy resin (B) and the curing agent (C) can be dissolved therein.
  • Examples thereof include ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, aromatic hydrocarbons such as benzene, toluene, and xylene, and amides such as dimethylformamide and diemthylacetamide.
  • the laminated sheet according to the present invention is a lamination molded product prepared using the prepreg.
  • the laminated sheet is produced by providing a single sheet of the prepreg or a stack of a plurality of sheets of the prepreg, optionally placing a metal foil of copper or aluminum on one surface or both surfaces of the single prepreg or the stack, and subjecting the assembly to molding.
  • Any metal foil used in materials for printed wiring boards may be used without particular limitation.
  • Techniques for conventional laminated sheets for printing wiring boards or multilayered boards may be adopted in the lamination molding.
  • the lamination molding is generally carried out under conditions of the use of a multistage press, a multistage vacuum press, continuous molding machine, an autoclave molding machine or the like, a temperature of 100 to 300° C., a pressure of 2 to 100 kgf/cm 2 , and a heating time of 0.05 to 5 hr.
  • a multilayered board can be formed by lamination molding of a combination of the prepreg with a separately provided wiring board for an internal layer.
  • the present invention is further illustrated by the following Synthesis Examples, Examples, and Comparative Examples.
  • a reactor equipped with a thermometer, a stirrer, a dropping funnel, and a reflux condenser was preliminarily cooled with brine to 0 to 5° C.
  • Cyanogen chloride (7.47 g, 0.122 mol), 9.75 g (0.0935 mol) of 35% hydrochloric acid, 76 ml of water, and 44 ml of methylene chloride were charged into the reactor.
  • the temperature within the reactor and pH were kept at ⁇ 5 to +5° C.
  • the cyanate ester resin thus obtained was analyzed by liquid chromatography and an IR spectrum. As a result, peaks attributable to raw materials were not detected. Further, the structure of the cyanate ester resin was identified by 13C-NMR and 1H-NMR. As a result, it was found that the conversion of the hydroxyl group to the cyanate group was not less than 99%.
  • a novolak cyanate ester resin (Primaset PT-30, manufactured by Lonza Japan, cyanate equivalent: 124 g/eq.) (50 parts by weight) and 50 parts by weight of bis(3-ethyl-5-methyl-4-maleimidephenyl)methane (BMI-70: manufactured by K.I. Kasei K.K.) were melted at 150° C. and were allowed to react with each other until the viscosity of the mixed resin became 15 Pa ⁇ s as measured with a cone-plate viscometer with stirring. The mixed resin was dissolved in methyl ethyl ketone to obtain a BT resin.
  • BMI-70 bis(3-ethyl-5-methyl-4-maleimidephenyl)methane
  • the varnish was diluted with methyl ethyl ketone.
  • the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
  • the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 4 min to obtain a prepreg having a resin content of 50% by weight.
  • a 12 ⁇ m-thick electrolytic copper foil (3EC-III, manufactured by MITSUI MINING & SMELTING CO., LTD.) was placed on the upper surface and the lower surface of the stack, followed by lamination molding under conditions of a pressure of 30 kgf/cm 2 , a temperature of 220° C., and a time of 120 min to obtain a metal foil-clad laminated sheet having a 0.4 mm-thick insulating layer.
  • the copper foil was removed by etching the metal foil-clad laminated sheet before the flame retardance and coefficient of thermal expansion were evaluated by the following method.
  • Flame retardance evaluated according to a UL94 vertical combustion testing method using the 0.8 mm-thick etched laminated sheet.
  • Glass transition temperature measured with a dynamic viscoelasticity analyzer (manufactured by TA INSTRUMENTS) according to JIS (Japanese Industrial Standards) C 6481.
  • Coefficient of thermal expansion determined by providing a thermomechanical analyzer (manufactured by TA INSTRUMENTS), raising the temperature from 40° C. to 340° C. at a temperature rise rate of 10° C./min, and measuring a coefficient of linear expansion in a plane direction from 60° C. to 120° C. The measurement direction was a warp direction of the glass cloth in the laminated sheet.
  • the heat resistance for the metal foil-clad laminated sheets was evaluated by the following method.
  • Heat resistance A sample having a size of 50 ⁇ 50 mm was floated in a solder of 300° C. for 30 min, and the time taken until the occurrence of delamination was measured. When the delamination did not occur until 30 min elapsed from the start of floating in the solder, the heat resistance was expressed as >30 min in the table.
  • the drilling workability was evaluated in terms of the accuracy of hole positions under the following drilling conditions.
  • Example 1 The procedure of Example 1 was repeated, except that 55 parts by weight of a naphthol aralkyl phenolic resin (SN-495) and 45 parts by weight of a phenol novolak epoxy resin (EPICLON N-770, epoxy equivalent: 190 g/eq., manufactured by DIC) as an epoxy resin were used.
  • a naphthol aralkyl phenolic resin SN-495
  • a phenol novolak epoxy resin EPICLON N-770, epoxy equivalent: 190 g/eq., manufactured by DIC
  • Example 1 The procedure of Example 1 was repeated, except that 20 parts by weight of a naphthalene phenolic resin (EPICLON EXB-9500, manufactured by DIC, hydroxyl group equivalent: 153 g/eq.), 20 parts by weight of a biphenyl aralkyl phenolic resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl group equivalent: 231 g/eq.), and 60 parts by weight of a phenol biphenyl aralkyl epoxy resin (NC-3000-FH) were used instead of the naphthol aralkyl phenolic resin.
  • a naphthalene phenolic resin EPICLON EXB-9500, manufactured by DIC, hydroxyl group equivalent: 153 g/eq.
  • a biphenyl aralkyl phenolic resin KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl group equivalent
  • Example 1 The procedure of Example 1 was repeated, except that 25 parts by weight of a naphthalene phenolic resin (EPICLON EXB-9500, manufactured by DIC, hydroxyl group equivalent:153 g/eq.) and 25 parts by weight of a biphenyl aralkyl phenolic resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl group equivalent: 231 g/eq.) were used instead of the naphthol aralkyl phenolic resin, and 50 parts by weight of a phenol novolak epoxy resin (N-770, epoxy equivalent: 190 g/eq., manufactured by DIC) was used instead of the phenol biphenyl aralkyl epoxy resin.
  • a naphthalene phenolic resin EPICLON EXB-9500, manufactured by DIC, hydroxyl group equivalent:153 g/eq.
  • a biphenyl aralkyl phenolic resin (KA
  • Example 1 The procedure of Example 1 was repeated, except that the amount of the naphthol aralkyl phenolic resin was reduced by 10 parts by weight, the amount of the phenol biphenyl aralkyl epoxy resin was reduced by 10 parts by weight, 20 parts by weight of bis(3-ethyl-5-methyl-4-maleimidephenyl)methane was used instead of the reduced 20 parts by weight, and the talc coated with zinc molybdate (ChemGuard 911C) was not used.
  • Example 2 The procedure of Example 2 was repeated, except that the amount of the naphthol aralkyl phenolic resin was reduced by 10 parts by weight, the amount of the phenol novolak epoxy resin was reduced by 10 parts by weight, 20 parts by weight of bis(3-ethyl-5-methyl-4-maleimidephenyl)methane was used instead of the reduced 20 parts by weight, and the talc coated with zinc molybdate (ChemGuard 911C) was not used.
  • Example 3 The procedure of Example 3 was repeated, except that the amount of the naphthalene phenolic resin (EPICLON EXB-9500) was reduced by 5 parts by weight, the amount of the biphenyl aralkyl phenolic resin (KAYAHARD GPH-103) was reduced by 5 parts by weight, the amount of the phenol biphenyl aralkyl epoxy resin was reduced by 10 parts by weight, 20 parts by weight of bis(3-ethyl-5-methyl-4-maleimidephenyl)methane was used instead of the reduced 20 parts by weight, and the talc coated with zinc molybdate (ChemGuard 911C) was not used.
  • the naphthalene phenolic resin EPICLON EXB-9500
  • the amount of the biphenyl aralkyl phenolic resin KAYAHARD GPH-103
  • the amount of the phenol biphenyl aralkyl epoxy resin was reduced by 10 parts by weight
  • Example 4 The procedure of Example 4 was repeated, except that the amount of the naphthalene phenolic resin (EPICLON EXB-9500) was reduced by 5 parts by weight, the amount of the biphenyl aralkyl phenolic resin (KAYAHARD GPH-103) was reduced by 5 parts by weight, the amount of the phenol novolak epoxy resin was reduced by 10 parts by weight, 20 parts by weight of bis(3-ethyl-5-methyl-4-maleimidephenyl)methane was used instead of the reduced 20 parts by weight, and the talc coated with zinc molybdate (ChemGuard 911C) was not used.
  • EPICLON EXB-9500 the amount of the biphenyl aralkyl phenolic resin
  • KAYAHARD GPH-103 the amount of the phenol novolak epoxy resin was reduced by 10 parts by weight
  • 20 parts by weight of bis(3-ethyl-5-methyl-4-maleimidephenyl)methane was used instead of the reduced
  • Example 5 The procedure of Example 5 was repeated, except that 10 parts by weight of a silicone powder (KMP-605) was added.
  • KMP-605 a silicone powder
  • Example 6 The procedure of Example 6 was repeated, except that 10 parts by weight of a silicone powder (KMP-605) was added.
  • Example 7 The procedure of Example 7 was repeated, except that 10 parts by weight of a silicone powder (KMP-605) was added.
  • Example 8 The procedure of Example 8 was repeated, except that 10 parts by weight of a silicone powder (KMP-605) was added.
  • Example 5 The procedure of Example 5 was repeated, except that 20 parts by weight of a silicone powder (KMP-605) was added.
  • KMP-605 a silicone powder
  • UltraCarb1200 90 parts by weight of an inorganic filler (
  • Example 9 The procedure of Example 9 was repeated, except that 200 parts by weight of an inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (UltraCarb1200) was added.
  • A an inorganic filler that is a mixture composed of hydromagnesite and huntite
  • Example 9 The procedure of Example 9 was repeated, except that 5 parts by weight of an inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (UltraCarb1200) and 85 parts by weight of spherical slica (SFP-130MC; manufactured by Denki Kagaku Kogyo K.K.; particle diameter 0.7 ⁇ m) were added.
  • A inorganic filler
  • SFP-130MC spherical slica
  • Example 1 The procedure of Example 1 was repeated, except that 45 parts by weight of an ⁇ -Naphthol aralkyl cyanate ester compound (cyanate equivalent: 261 g/eq.) prepared in Synthesis Example 1 was used instead of the naphthol aralkyl phenolic resin.
  • an ⁇ -Naphthol aralkyl cyanate ester compound (cyanate equivalent: 261 g/eq.) prepared in Synthesis Example 1 was used instead of the naphthol aralkyl phenolic resin.
  • Example 17 The procedure of Example 17 was repeated, except that a prepolymer of 2,2-bis(4-cyanatophenyl)propane (CA210, cyanate equivalent: 139, manufacured by Mitsubishi Gas Chemical Co., Inc.) (30 parts by weight) was used instead of the ⁇ -naphthol aralkyl cyanate ester compound prepared in Synthesis Example 1 and the phenol biphenyl aralkyl epoxy resin (NC-3000-FH) was used in an amount of 70 parts by weight.
  • CA210 2,2-bis(4-cyanatophenyl)propane
  • NC-3000-FH phenol biphenyl aralkyl epoxy resin
  • Example 18 The procedure of Example 18 was repeated, except that 40 parts by weight of a prepolymer of 2,2-bis(4-cyanatephenyl)propane (CA210, cyanate equivalent 139, manufactured by Mitsubishi Gas Chemical Co., Inc.) and 60 parts by weight of a phenol novolak epoxy resin (N-770) were used.
  • CA210 2,2-bis(4-cyanatephenyl)propane
  • N-770 a phenol novolak epoxy resin
  • Example 17 The procedure of Example 17 was repeated, except that the amount of the ⁇ -naphthol aralkyl cyanate ester compound prepared in Synthesis Example 1 was reduced by 10 parts by weight, the amount of the phenol biphenyl aralkyl epoxy resin (NC-3000-FH) was reduced by 10 parts by weight, 20 parts by weight of bis(3-ethyl-5-methyl-4-maleimidephenyl)methane was used instead of the reduced 20 parts by weight, and the talc coated with zinc molybdate (ChemGuard 911C) was not used.
  • NC-3000-FH phenol biphenyl aralkyl epoxy resin
  • Example 18 The procedure of Example 18 was repeated, except that the amount of the prepolymer of 2,2-bis(4-cyanatophenyl)propane (CA210) was reduced by 5 parts by weight, the amount of the phenol biphenyl aralkyl epoxy resin (NC-3000-FH) was reduced by 15 parts by weight, 20 parts by weight of bis(3-ethyl-5-methyl-4-maleimidephenyl)methane was used instead of the reduced 20 parts by weight, and the talc coated with zinc molybdate (ChemGuard 911C) was not used.
  • CA210 2,2-bis(4-cyanatophenyl)propane
  • NC-3000-FH phenol biphenyl aralkyl epoxy resin
  • Example 19 The procedure of Example 19 was repeated, except that the amount of the ⁇ -naphthol aralkyl cyanate ester compound prepared in Synthesis Example 1 was reduced by 15 parts by weight, the amount of the phenol novolak epoxy resin (N-770) was reduced by 5 parts by weight, 20 parts by weight of bis(3-ethyl-5-methyl-4-maleimidephenyl)methane was used instead of the reduced 20 parts by weight, and the talc coated with zinc molybdate (ChemGuard 911C) was not used.
  • Example 20 The procedure of Example 20 was repeated, except that the amount of the prepolymer of 2,2-bis(4-cyanatephenyl)propane (CA210) was reduced by 5 parts by weight, the amount of the phenol novolak epoxy resin (N-770) was reduced by 15 parts by weight, 20 parts by weight of bis(3-ethyl-5-methyl-4-maleimidephenyl)methane was used instead of the reduced 20 parts by weight, and the talc coated with zinc molybdate (ChemGuard 911C) was not used.
  • Example 21 The procedure of Example 21 was repeated, except that 10 parts by weight of a silicone powder (KMP-605) was added.
  • a prepreg was obtained in the same manner as in Example 22, except that 10 parts by weight of a silicone powder (KMP-605) was added.
  • Example 23 The procedure of Example 23 was repeated, except that 10 parts by weight of a silicone powder (KMP-605) was added.
  • Example 24 The procedure of Example 24 was repeated, except that 10 parts by weight of a silicone powder (KMP-605) was added.
  • A inorganic filler
  • This varnish was diluted with methyl ethyl ketone.
  • the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
  • the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 4 min to obtain a prepreg having a resin content of 50% by weight.
  • a metal foil-clad laminated sheet was obtained in the same manner as in Example 1.
  • Example 29 The procedure of Example 29 was repeated, except that 50 parts by weight of BT9510 (manufactured by Mitsubishi Gas Chemical Company, Inc.) prepared in Synthesis Example 3 was used as the BT resin and the phenol biphenyl aralkyl epoxy resin (NC-3000-FH) was used in an amount of 40 parts by weight.
  • BT9510 manufactured by Mitsubishi Gas Chemical Company, Inc.
  • NC-3000-FH phenol biphenyl aralkyl epoxy resin
  • Example 29 The procedure of Example 29 was repeated, except that the amount of the BT resin (BT2610) prepared in Synthesis Example 2 was reduced by 10 parts by weight, the amount of the phenol biphenyl aralkyl epoxy resin (NC-3000-FH) was reduced by 10 parts by weight, 20 parts by weight of bis(3-ethyl-5-methyl-4-maleimidephenyl)methane was used instead of the reduced 20 parts by weight, and the talc coated with zinc molybdate (ChemGuard 911C) was not used.
  • BT resin BT2610
  • N-FH phenol biphenyl aralkyl epoxy resin
  • Example 30 The procedure of Example 30 was repeated, except that the amount of the BT resin (BT9510) prepared in Synthesis Example 3 was reduced by 10 parts by weight, the amount of the phenol biphenyl aralkyl epoxy resin (NC-3000-FH) was reduced by 10 parts by weight, 20 parts by weight of bis(3-ethyl-5-methyl-4-maleimidephenyl)methane was used instead of the reduced 20 parts by weight, and the talc coated with zinc molybdate (ChemGuard 911C) was not used.
  • BT resin BT9510
  • N-FH phenol biphenyl aralkyl epoxy resin
  • Example 31 The procedure of Example 31 was repeated, except that 10 parts by weight of a silicone powder (KMP-605) was added.
  • Example 32 The procedure of Example 32 was repeated, except that 10 parts by weight of a silicone powder (KMP-605) was added.
  • a biphenyl aralkyl phenolic resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl group equivalent: 231 g/eq.) (10 parts by weight), 55 parts by weight of the BT resin (BT2610) prepared in Synthesis Example 2, 25 parts by weight of a phenol biphenyl aralkyl epoxy resin (NC-3000-FH), 10 parts by weight of a phenol novolak epoxy resin (N-770), 1.5 parts by weight of a wetting/dispersing agent (BYK-W903), 90 parts by weight of an inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200), 10 parts by weight of talc coated with zinc molybdate (ChemGuard 911C), and 0.01 part by weight of zinc octylate were mixed together to obtain a varnish.
  • A inorganic filler
  • This varnish was diluted with methyl ethyl ketone.
  • the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
  • the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 4 min to obtain a prepreg having a resin content of 50% by weight.
  • a metal laminated sheet was obtained in the same manner as in Example 1.
  • Example 35 The procedure of Example 35 was repeated, except that 40 parts by weight of BT9510 prepared in Synthesis Example 3 was used as the BT resin and the phenol biphenyl aralkyl epoxy resin (NC-3000-FH) was used in an amount of 40 parts by weight.
  • Example 35 The procedure of Example 35 was repeated, except that the amount of the biphenyl aralkyl phenolic resin (KAYAHARD GPH-103) was reduced by 5 parts by weight, the amount of the BT resin (BT2610) prepared in Synthesis Example 2 was reduced by 5 parts by weight, the amount of the phenol biphenyl aralkyl epoxy resin (NC-3000-FH) was reduced by 5 parts by weight, the amount of the phenol novolak epoxy resin (N-770) was reduced by 5 parts by weight, 20 parts by weight of bis(3-ethyl-5-methyl-4-maleimidephenyl)methane was used instead of the reduced 20 parts by weight, and the talc coated with zinc molybdate (ChemGuard 911C) was not used.
  • the amount of the biphenyl aralkyl phenolic resin (KAYAHARD GPH-103) was reduced by 5 parts by weight
  • the amount of the BT resin (BT2610) prepared in Synthesis Example 2 was reduced by 5 parts by weight
  • Example 36 The procedure of Example 36 was repeated, except that the amount of the biphenyl aralkyl phenolic resin (KAYAHARD GPH-103) was reduced by 5 parts by weight, the amount of the BT resin (BT9510) prepared in Synthesis Example 3 was reduced by 5 parts by weight, the amount of the phenol biphenyl aralkyl epoxy resin (NC-3000-FH) was reduced by 5 parts by weight, the amount of the phenol novolak epoxy resin (N-770) was reduced by 5 parts by weight, 20 parts by weight of bis(3-ethyl-5-methyl-4-maleimidephenyl)methane was used instead of the reduced 20 parts by weight, and the talc coated with zinc molybdate (ChemGuard 911C) was not used.
  • the biphenyl aralkyl phenolic resin (KAYAHARD GPH-103) was reduced by 5 parts by weight
  • the amount of the BT resin (BT9510) prepared in Synthesis Example 3 was reduced by 5 parts by weight
  • Example 37 The procedure of Example 37 was repeated, except that 10 parts by weight of a silicone powder (KMP-605) was added.
  • Example 38 The procedure of Example 38 was repeated, except that 10 parts by weight of a silicone powder (KMP-605) was added.
  • Example 1 The procedure of Example 1 was repeated, except that 10 parts by weight of a biphenyl aralkyl phenolic resin (KAYAHARD GPH-103), 10 parts by weight of the ⁇ -naphthol aralkyl cyanate ester compound prepared in Synthesis Example 1, 45 parts by weight of the BT resin (BT2610) prepared in Synthesis Example 2, 25 parts by weight of a phenol biphenyl aralkyl epoxy resin (NC-3000-FH), 10 parts by weight of a phenol novolak epoxy resin (N-770), 1.5 parts by weight of a wetting/dispersing agent (BYK-W903), 90 parts by weight of an inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200), 10 parts by weight of talc coated with zinc molybdate (ChemGuard 911C), and 0.01 part by weight of zinc octylate were used.
  • A inorganic filler
  • Example 1 The procedure of Example 1 was repeated, except that 10 parts by weight of a biphenyl aralkyl phenolic resin (KAYAHARD GPH-103), 10 parts by weight of a novolak cyanate ester compound (Primaset PT-30), 35 parts by weight of the BTresin (BT9510) prepared in Synthesis Example 3, 35 parts by weight of a phenol biphenyl aralkyl epoxy resin (NC-3000-FH), 10 parts by weight of a phenol novolak epoxy resin (N-770), 1.5 parts by weight of a wetting/dispersing agent (BYK-W903), 90 parts by weight of an inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200), 10 parts by weight of talc coated with zinc molybdate (ChemGuard 911C), and 0.01 part by weight of zinc octylate were used.
  • A inorganic filler
  • Ultracarb1200 10
  • Example 1 The procedure of Example 1 was repeated, except that 10 parts by weight of the ⁇ -naphthol aralkyl cyanate ester compound prepared in Synthesis Example 1, 50 parts by weight of the BT resin (BT2610) prepared in Synthesis Example 2, 30 parts by weight of a phenol biphenyl aralkyl epoxy resin (NC-3000-FH), 10 parts by weight of a phenol novolak epoxy resin (N-770), 1.5 parts by weight of a wetting/dispersing agent (BYK-W903), 90 parts by weight of an inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200), 10 parts by weight of talc coated with zinc molybdate (ChemGuard 911C), and 0.01 part by weight of zinc octylate were used.
  • A inorganic filler that is a mixture composed of hydromagnesite and huntite
  • Ultracarb1200 10 parts by weight of talc coated with zinc
  • Example 1 The procedure of Example 1 was repeated, except that 10 parts by weight of a novolak cyanate ester compound (Primaset PT-30), 40 parts by weight of the BT resin (BT9510) prepared in Synthesis Example 3, 40 parts by weight of a phenol biphenyl aralkyl epoxy resin (NC-3000-FH), 10 parts by weight of a phenol novolak epoxy resin (N-770), 1.5 parts by weight of a wetting/dispersing agent (BYK-W903), 90 parts by weight of an inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200), 10 parts by weight of talc coated with zinc molybdate (ChemGuard 911C), and 0.01 part by weight of zinc octylate were used.
  • a novolak cyanate ester compound Primerative cyanate ester compound
  • BT9510 a phenol biphenyl aralkyl epoxy resin
  • N-770 phenol
  • Example 1 The procedure of Example 1 was repeated, except that 10 parts by weight of a biphenyl aralkyl phenolic resin (KAYAHARD GPH-103), 40 parts by weight of the ⁇ -naphthol aralkyl cyanate ester compound prepared in Synthesis Example 1, 50 parts by weight of a phenol biphenyl aralkyl epoxy resin (NC-3000-FH), 1.5 parts by weight of a wetting/dispersing agent (BYK-W903), 90 parts by weight of an inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200), 10 parts by weight of talc coated with zinc molybdate (ChemGuard 911C), and 0.01 part by weight of zinc octylate were used.
  • a biphenyl aralkyl phenolic resin (KAYAHARD GPH-103)
  • Example 1 The procedure of Example 1 was repeated, except that 10 parts by weight of a biphenyl aralkyl phenolic resin (KAYAHARD GPH-103), 40 parts by weight of a novolak cyanate ester compound (Primaset PT-30), 40 parts by weight of a phenol biphenyl aralkyl epoxy resin (NC-3000-FH), 10 parts by weight of a phenol novolak epoxy resin (N-770), 1.5 parts by weight of a wetting/dispersing agent (BYK-W903), 90 parts by weight of an inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200), 10 parts by weight of talc coated with zinc molybdate (ChemGuard 911C), and 0.01 part by weight of zinc octylate were used.
  • A inorganic filler
  • Ultracarb1200 10 parts by weight of talc coated with zinc molybdate
  • Example 3 The procedure of Example 3 was repeated, except that 250 parts by weight of an inorganic filler (A) that is a mixture composed of hydromagnesite and huntite was added.
  • A inorganic filler
  • Example 1 The procedure of Example 1 was repeated, except that 90 parts by weight of spherical silica (SFP-130MC) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200). The product was inferior in accuracy of hole position to that in Example 1.
  • SFP-130MC spherical silica
  • A the inorganic filler
  • Example 1 The procedure of Example 1 was repeated, except that 40 parts by weight of spherical silica (SFP-130MC) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • SFP-130MC spherical silica
  • A the inorganic filler
  • Ultracarb1200 hydromagnesite and huntite
  • Example 1 The procedure of Example 1 was repeated, except that 90 parts by weight of boehmite (APYRAL AOH60, manufactured by Nabaltec) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • A the inorganic filler
  • Ultracarb1200 The product was larger in coefficient of thermal expansion and was also lower in flame retardance than the product in Example 1.
  • Example 1 The procedure of Example 1 was repeated, except that 120 parts by weight of boehmite (APYRAL AOH60) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • A the inorganic filler that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • the product was larger in coefficient of thermal expansion, was lower in flame retardance, and was lower in the accuracy of hole position than that in Example 1.
  • Example 3 The procedure of Example 3 was repeated, except that 90 parts by weight of aluminum hydroxide (CL-303, manufactured by Sumitomo Chemical Co., Ltd.) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200), 40 parts by weight of a phenolic resin (PHENOLITE TD-2093, manufactured by DIC, hydroxyl group equivalent: 105) was used instead of 20 parts by weight of the naphthalene phenolic resin (EPICLON EXB-9500) and 20 parts by weight of the biphenyl aralkyl phenolic resin (KAYAHARD GPH-103), and 60 parts by weight of a phenol novolak epoxy resin (DEN438, manufactured by The Dow Chemical Company, epoxy equivalent: 179 g/eq.) was used instead 60 parts by weight of the phenol biphenyl aralkyl epoxy resin (NC-3000-FH).
  • CL-303 aluminum hydroxide
  • Example 3 The procedure of Example 3 was repeated, except that 90 parts by weight of magnesium hydroxide (Kisuma 8SN, manufactured by Kyowa Chemical Industry, Co., Ltd.) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200), 40 parts by weight of a phenolic resin (TD-2093) was used instead of 20 parts by weight of the naphthalene phenolic resin (EPICLON EXB-9500) and 20 parts by weight of the biphenyl aralkyl phenolic resin (KAYAHARD GPH-103), and 60 parts by weight of a phenol novolak epoxy resin (DEN438) was used instead of the phenol biphenyl aralkyl epoxy resin (NC-3000-FH).
  • the product was larger in coefficient of thermal expansion, was lower in flame retardance, and was lower in heat resistance than the product in Example 3.
  • Example 5 The procedure of Example 5 was repeated, except that 90 parts by weight of spherical silica (SFP-130MC) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200). The product was inferior in accuracy of hole position to that in Example 5.
  • SFP-130MC spherical silica
  • Ultracarb1200 the inorganic filler
  • Example 5 The procedure of Example 5 was repeated, except 40 parts by weight of spherical silica (SFP-130MC) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • SFP-130MC spherical silica
  • A the inorganic filler that is a mixture composed of hydromagnesite and huntite
  • Example 5 The procedure of Example 5 was repeated, except that 90 parts by weight of boehmite (APYRAL AOH60) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • A the inorganic filler that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • the product was larger in coefficient of thermal expansion and was lower in flame retardance than the product in Example 5.
  • Example 5 The procedure of Example 5 was repeated, except that 120 parts by weight of boehmite (APYRAL AOH60) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • A the inorganic filler that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • the product was larger in coefficient of thermal expansion, was lower in flame retardance, and was lower in the accuracy of hole position than the product in Example 5.
  • Example 7 The procedure of Example 7 was repeated, except that 90 parts by weight of aluminum hydroxide (CL-303) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200), 40 parts by weight of a phenolic resin (TD-2093) was used instead of 15 parts by weight of the naphthalene phenolic resin (EPICLON EXB-9500) and 15 parts by weight of the biphenyl aralkyl phenolic resin (KAYAHARD GPH-103), and 50 parts by weight of a phenol novolak epoxy resin (DEN438) was used instead of 50 parts by weight of the phenol biphenyl aralkyl epoxy resin (NC-3000-FH).
  • CL-303 aluminum hydroxide
  • A inorganic filler
  • A inorganic filler
  • TD-2093 40 parts by weight of a phenolic resin
  • TD-2093 was used instead of 15 parts by weight of the n
  • Example 7 The procedure of Example 7 was repeated, except that 90 parts by weight of magnesium hydroxide (Kisuma 8SN) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200), 40 parts by weight of a phenolic resin (TD-2093) was used instead of 15 parts by weight of the naphthalene phenolic resin (EPICLON EXB-9500) and 15 parts by weight of the biphenyl aralkyl phenolic resin (KAYAHARD GPH-103), and 50 parts by weight of a phenol novolak epoxy resin (DEN438) was used instead of 50 parts by weight of the phenol biphenyl aralkyl epoxy resin (NC-3000-FH).
  • the product was larger in coefficient of thermal expansion, lower in flame retardance, and lower in heat resistance than that in Example 7.
  • Example 9 The procedure of Example 9 was repeated, except that 90 parts by weight of spherical silica (SFP-130MC) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200). The product was lower in the accuracy of hole position than that in Example 9.
  • SFP-130MC spherical silica
  • A inorganic filler
  • Example 9 The procedure of Example 9 was repeated, except that 40 parts by weight of spherical silica (SFP-130MC) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200). The product was larger in coefficient of thermal expansion and lower in flame retardance than that in Example 9.
  • SFP-130MC spherical silica
  • Ultracarb1200 hydromagnesite and huntite
  • Example 9 The procedure of Example 9 was repeated, except that 90 parts by weight of boehmite (APYRAL AOH60) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200). The product was lower in flame retardance than that in Example 9.
  • A boehmite
  • Ultracarb1200 the inorganic filler
  • Example 9 The procedure of Example 9 was repeated, except that 120 parts by weight of boehmite (APYRAL AOH60) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200). The product was lower in flame retardance than that in Example 9.
  • A boehmite
  • Ultracarb1200 the inorganic filler
  • Example 11 The procedure of Example 11 was repeated, except that 90 parts by weight of aluminum hydroxide (CL-303) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200), 40 parts by weight of a phenolic resin (TD-2093) was used instead of 15 parts by weight of the naphthalene phenolic resin (EPICLON EXB-9500) and 15 parts by weight of the biphenyl aralkyl phenolic resin (KAYAHARD GPH-103), and 50 parts by weight of a phenol novolak epoxy resin (DEN438) was used instead of 50 parts by weight of the phenol biphenyl aralkyl epoxy resin (NC-3000-FH).
  • CL-303 aluminum hydroxide
  • A inorganic filler
  • A inorganic filler
  • TD-2093 40 parts by weight of a phenolic resin
  • TD-2093 was used instead of 15 parts by weight of the n
  • Example 11 The procedure of Example 11 was repeated, except that 90 parts by weight of magnesium hydroxide (Kisuma 8SN) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200), 40 parts by weight of a phenolic resin (TD-2093) was used instead of 15 parts by weight of the naphthalene phenolic resin (EPICLON EXB-9500) and 15 parts by weight of the biphenyl aralkyl phenolic resin (KAYAHARD GPH-103), and 50 parts by weight of a phenol novolak epoxy resin (DEN438) was used instead of 50 parts by weight of the phenol biphenyl aralkyl epoxy resin (NC-3000-FH).
  • the product was larger in coefficient of thermal expansion and lower in heat resistance than that in Example 11.
  • Example 17 The procedure of Example 17 was repeated, except that 90 parts by weight of spherical silica (SFP-130MC) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • SFP-130MC spherical silica
  • A the inorganic filler
  • Ultracarb1200 hydromagnesite and huntite
  • Example 17 The procedure of Example 17 was repeated, except that 40 parts by weight of spherical silica (SFP-130MC) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • SFP-130MC spherical silica
  • A the inorganic filler
  • Ultracarb1200 hydromagnesite and huntite
  • Example 17 The procedure of Example 17 was repeated, except that 90 parts by weight of boehmite (APYRAL AOH60) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • A the inorganic filler that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • the product was larger in coefficient of thermal expansion and lower in flame retardance than that in Example 17.
  • Example 17 The procedure of Example 17 was repeated, except that 120 parts by weight of boehmite (APYRAL AOH60) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • A the inorganic filler that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • the product was larger in coefficient of thermal expansion, lower in flame retardance, and lower in the accuracy of hole position than that in Example 17.
  • Example 17 The procedure of Example 17 was repeated, except that 90 parts by weight of aluminum hydroxide (CL-303) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • CL-303 aluminum hydroxide
  • A inorganic filler
  • the product was larger in coefficient of thermal expansion, lower in flame retardance, and lower in heat resistance than that in Example 17.
  • Example 21 The procedure of Example 21 was repeated, except that 90 parts by weight of spherical silica (SFP-130MC) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • SFP-130MC spherical silica
  • A the inorganic filler that is a mixture composed of hydromagnesite and huntite
  • Example 21 The procedure of Example 21 was repeated, except that 40 parts by weight of spherical silica (SFP-130MC) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • SFP-130MC spherical silica
  • A the inorganic filler
  • Ultracarb1200 hydromagnesite and huntite
  • Example 21 The procedure of Example 21 was repeated, except that 90 parts by weight of boehmite (APYRAL AOH60) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • A the inorganic filler that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • the product was larger in coefficient of thermal expansion and lower in flame retardance than that in Example 21.
  • Example 21 The procedure of Example 21 was repeated, except that 120 parts by weight of boehmite (APYRAL AOH60) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • the product was larger in coefficient of thermal expansion, lower in flame retardance, lower in the accuracy of hole position than that in Example 21.
  • Example 21 The procedure of Example 21 was repeated, except that 90 parts by weight of aluminum hydroxide (CL-303) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • CL-303 aluminum hydroxide
  • A inorganic filler
  • the product was larger in coefficient of thermal expansion, lower in flame retardance, lower in heat resistance than that in Example 21.
  • Example 21 The procedure of Example 21 was repeated, except that 120 parts by weight of magnesium hydroxide (Kisuma 8SN) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • the product was larger in coefficient of thermal expansion, lower in flame retardance, lower in heat resistance than that in Example 21.
  • Example 25 The procedure of Example 25 was repeated, except that 90 parts by weight of spherical silica (SFP-130MC) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200). The product was lower in the accuracy of hole position than that in Example 25.
  • SFP-130MC spherical silica
  • A the inorganic filler
  • Example 25 The procedure of Example 25 was repeated, except that 40 parts by weight of spherical silica (SFP-130MC) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • SFP-130MC spherical silica
  • A the inorganic filler that is a mixture composed of hydromagnesite and huntite
  • Example 25 The procedure of Example 25 was repeated, except that 90 parts by weight of boehmite (APYRAL AOH60) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • A the inorganic filler that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • the product was larger in coefficient of thermal expansion and lower in flame retardance than that in Example 25.
  • Example 25 The procedure of Example 25 was repeated, except that 120 parts by weight of boehmite (APYRAL AOH60) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • A the inorganic filler that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • the product was larger in coefficient of thermal expansion and lower in flame retardance than that in Example 25.
  • Example 25 The procedure of Example 25 was repeated, except that 90 parts by weight of aluminum hydroxide (CL-303) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200).
  • CL-303 aluminum hydroxide
  • A inorganic filler
  • the product was larger in coefficient of thermal expansion and lower in heat resistance than that in Example 25.
  • Example 25 The procedure of Example 25 was repeated, except that 120 parts by weight of magnesium hydroxide (Kisuma 8SN) was used instead of 90 parts by weight of the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200). The product was larger in coefficient of thermal expansion, lower in heat resistance than that in Example 25.
  • Example 3 The procedure of Example 3 was repeated, except that the inorganic filler (A) that is a mixture composed of hydromagnesite and huntite (Ultracarb1200) was not added.
  • the product was larger in coefficient of thermal expansion, lower in flame retardance than that in Example 3.
  • Example 3 The procedure of Example 3 was repeated, except that the phenol biphenyl aralkyl epoxy resin (NC-3000-FH) was not added. As a result, the product was not cured.
  • the phenol biphenyl aralkyl epoxy resin NC-3000-FH
  • Example 3 The procedure of Example 3 was repeated, except that the naphthalene phenolic resin (EPICLON EXB-9500) and the biphenyl aralkyl phenolic resin (KAYAHARD GPH-103) were not added. As a result, the product was not cured.
  • Example 3 The procedure of Example 3 was repeated, except that the phenol biphenyl aralkyl epoxy resin (NC-3000-FH) was changed to a polyethylene resin (Novatec HD, manufactured by Japan Polyethylene Corporation). As a result, the product was not cured.
  • the laminated sheets obtained using the prepregs according to the present invention have a high level of heat resistance, a low coefficient of thermal expansion, and a high level of drilling workability and, at the same time, can retain a high level of flame retardance without the need to use halogenated flame retardants and phosphorus compounds as flame retardants.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Inorganic Chemistry (AREA)
  • Reinforced Plastic Materials (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Laminated Bodies (AREA)
  • Epoxy Resins (AREA)
US13/816,008 2010-08-31 2011-08-29 Resin composition, prepreg, and laminate Abandoned US20130136930A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2010-194390 2010-08-31
JP2010194390 2010-08-31
PCT/JP2011/069393 WO2012029690A1 (ja) 2010-08-31 2011-08-29 樹脂組成物、プリプレグ、および積層板

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2011/069393 A-371-Of-International WO2012029690A1 (ja) 2010-08-31 2011-08-29 樹脂組成物、プリプレグ、および積層板

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US15/363,395 Division US9902825B2 (en) 2010-08-31 2016-11-29 Resin composition, prepreg, and laminated sheet

Publications (1)

Publication Number Publication Date
US20130136930A1 true US20130136930A1 (en) 2013-05-30

Family

ID=45772778

Family Applications (2)

Application Number Title Priority Date Filing Date
US13/816,008 Abandoned US20130136930A1 (en) 2010-08-31 2011-08-29 Resin composition, prepreg, and laminate
US15/363,395 Active US9902825B2 (en) 2010-08-31 2016-11-29 Resin composition, prepreg, and laminated sheet

Family Applications After (1)

Application Number Title Priority Date Filing Date
US15/363,395 Active US9902825B2 (en) 2010-08-31 2016-11-29 Resin composition, prepreg, and laminated sheet

Country Status (8)

Country Link
US (2) US20130136930A1 (ja)
EP (1) EP2612885B1 (ja)
JP (1) JP6157121B2 (ja)
KR (1) KR20130141449A (ja)
CN (2) CN103080225A (ja)
SG (2) SG10201506152WA (ja)
TW (1) TWI600700B (ja)
WO (1) WO2012029690A1 (ja)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140017502A1 (en) * 2011-01-20 2014-01-16 Mitsubishi Gas Chemical Company, Inc. Resin composition, prepreg and laminate
US20140227924A1 (en) * 2011-05-27 2014-08-14 Mitsubishi Gas Chemical Company, Inc. Resin composition, prepreg, and laminate
US20140288245A1 (en) * 2011-11-01 2014-09-25 Dow Corning Corporation High Glass Transition Temperature Resin Formulations
US20150014032A1 (en) * 2012-01-31 2015-01-15 Mitsubishi Gas Chemical Company, Inc. Resin composition for printed wiring board material, and prepreg, resin sheet, metal foil clad laminate, and printed wiring board using same
US20150364659A1 (en) * 2014-06-13 2015-12-17 General Electric Company Led package with red-emitting phosphors
US9902851B2 (en) 2012-10-19 2018-02-27 Mitsubishi Gas Chemical Company, Inc. Resin composition, prepreg, laminate, and printed wiring board
EP3339397A1 (en) * 2016-12-21 2018-06-27 Paroc Group Oy Fire-retardant composition and manufacturing process thereof, and insulation product comprising the fire-retardant composition and manufacturing process thereof
US10030141B2 (en) 2012-10-19 2018-07-24 Mitsubishi Gas Chemical Company, Inc. Resin composition, pre-preg, laminate, metal foil-clad laminate, and printed wiring board
US10178767B2 (en) 2012-11-28 2019-01-08 Mitsubishi Gas Chemical Company, Inc. Resin composition, prepreg, laminate, metallic foil clad laminate, and printed circuit board
US10655003B2 (en) 2010-10-14 2020-05-19 Lg Chem, Ltd. Resin blend for melting process

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI594882B (zh) 2011-07-22 2017-08-11 Ｌｇ化學股份有限公司 熱固型樹脂組成物及使用其之預浸材與覆金屬層壓板
JP6408752B2 (ja) * 2012-03-14 2018-10-17 日立化成株式会社 相溶化樹脂、およびそれを用いたプリプレグ、積層板
WO2014059654A1 (zh) * 2012-10-19 2014-04-24 广东生益科技股份有限公司 氰酸酯树脂组合物及使用其制作的预浸料、层压材料与覆金属箔层压材料
JP6183583B2 (ja) * 2013-02-14 2017-08-23 味の素株式会社 硬化性樹脂組成物
JP6217895B2 (ja) * 2013-02-14 2017-10-25 味の素株式会社 硬化性樹脂組成物
JP6308344B2 (ja) * 2013-04-08 2018-04-11 味の素株式会社 硬化性樹脂組成物
JP6468465B2 (ja) * 2013-06-18 2019-02-13 三菱瓦斯化学株式会社 樹脂組成物、プリプレグ、樹脂シート及び金属箔張り積層板
WO2015051541A1 (zh) * 2013-10-11 2015-04-16 广东生益科技股份有限公司 热固性树脂组合物及其用途
CN104403186B (zh) * 2014-11-14 2017-02-22 宁波一舟塑胶有限公司 一种复合协效阻燃抑烟的低烟无卤骨架料
JP2022521599A (ja) * 2019-02-22 2022-04-11 アルコア オブ オーストラリア リミテッド 肥料組成物

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4346012A (en) * 1979-05-15 1982-08-24 Dainippon Ink & Chemicals, Inc. Powdery fire-extinguishing agent, and process for its preparation
US6043306A (en) * 1998-05-22 2000-03-28 Kyowa Chemical Industry Co. Ltd. Flame-retardant thermoplastic resin composition
US6130282A (en) * 1997-10-01 2000-10-10 Kyowa Chemical Industry Co Ltd Flame retardant resin composition
US20060166760A1 (en) * 2005-01-24 2006-07-27 Bridgestone Sports Co., Ltd. Multi-piece solid golf ball
US7438898B1 (en) * 1998-07-30 2008-10-21 The Procter & Gamble Company Hair conditioning composition comprising carboxylic acid/carboxylate copolymer, and visible particle
US20100166684A1 (en) * 2008-12-25 2010-07-01 Kokyu Alcohol Kogyo Co., Ltd. Water-in-oil type emulsified cosmetic
US20110045213A1 (en) * 2006-09-29 2011-02-24 Dai Nippon Printing Co., Ltd. Thermal transfer sheet
US20110104222A1 (en) * 2008-06-11 2011-05-05 Kao Corporation Cosmetic

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02255843A (ja) 1988-11-22 1990-10-16 Furukawa Electric Co Ltd:The 難燃性樹脂組成物およびこれを用いた難燃性ケーブル
JPH03190965A (ja) * 1989-12-20 1991-08-20 Furukawa Electric Co Ltd:The 熱硬化性樹脂組成物
JP2592191B2 (ja) 1991-12-24 1997-03-19 積水樹脂株式会社 低発煙性難燃性樹脂組成物
DE59904252D1 (de) * 1998-12-09 2003-03-13 Vantico Ag Hydrophobes epoxidharzsystem
JP2002284844A (ja) 2001-03-23 2002-10-03 Sumitomo Bakelite Co Ltd エポキシ樹脂組成物及び半導体装置
JP2004059643A (ja) 2002-07-25 2004-02-26 Mitsubishi Gas Chem Co Inc プリプレグ及び積層板
JP4940680B2 (ja) 2006-02-06 2012-05-30 三菱瓦斯化学株式会社 樹脂組成物並びにそれを用いたプリプレグ及び積層板
CN101522792B (zh) * 2006-10-02 2013-01-09 日立化成工业株式会社 密封用环氧树脂成形材料以及电子零件装置
JP5024205B2 (ja) * 2007-07-12 2012-09-12 三菱瓦斯化学株式会社 プリプレグ及び積層板
CN102414262A (zh) 2009-02-25 2012-04-11 三菱瓦斯化学株式会社 预浸料和层压体
CN101643570B (zh) * 2009-08-24 2011-08-10 广东生益科技股份有限公司 无卤阻燃型树脂组合物及用其制成的预浸料、层压板与印制电路用层压板
US8031344B2 (en) 2009-10-30 2011-10-04 Hermes Microvision, Inc. Z-stage configuration and application thereof
US20130045650A1 (en) 2010-03-02 2013-02-21 Mitsubishi Gas Chemical Company, Inc. Resin composition, prepreg, and laminated sheet
WO2011126070A1 (ja) 2010-04-08 2011-10-13 三菱瓦斯化学株式会社 樹脂組成物、プリプレグおよび積層板

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4346012A (en) * 1979-05-15 1982-08-24 Dainippon Ink & Chemicals, Inc. Powdery fire-extinguishing agent, and process for its preparation
US6130282A (en) * 1997-10-01 2000-10-10 Kyowa Chemical Industry Co Ltd Flame retardant resin composition
US6043306A (en) * 1998-05-22 2000-03-28 Kyowa Chemical Industry Co. Ltd. Flame-retardant thermoplastic resin composition
US7438898B1 (en) * 1998-07-30 2008-10-21 The Procter & Gamble Company Hair conditioning composition comprising carboxylic acid/carboxylate copolymer, and visible particle
US20060166760A1 (en) * 2005-01-24 2006-07-27 Bridgestone Sports Co., Ltd. Multi-piece solid golf ball
US20110045213A1 (en) * 2006-09-29 2011-02-24 Dai Nippon Printing Co., Ltd. Thermal transfer sheet
US20110104222A1 (en) * 2008-06-11 2011-05-05 Kao Corporation Cosmetic
US20100166684A1 (en) * 2008-12-25 2010-07-01 Kokyu Alcohol Kogyo Co., Ltd. Water-in-oil type emulsified cosmetic

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Professional translation of JP 03190965 A, retreived 09/16/2014. *

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10655002B2 (en) 2010-10-14 2020-05-19 Lg Chem, Ltd. Resin blend for melting process
US10655003B2 (en) 2010-10-14 2020-05-19 Lg Chem, Ltd. Resin blend for melting process
US9955573B2 (en) * 2011-01-20 2018-04-24 Mitsubishi Gas Chemical Company, Inc. Resin composition, prepreg and laminate
US20140017502A1 (en) * 2011-01-20 2014-01-16 Mitsubishi Gas Chemical Company, Inc. Resin composition, prepreg and laminate
US20140227924A1 (en) * 2011-05-27 2014-08-14 Mitsubishi Gas Chemical Company, Inc. Resin composition, prepreg, and laminate
US9512329B2 (en) * 2011-05-27 2016-12-06 Mitsubishi Gas Chemical Company, Inc. Resin composition, prepreg, and laminate
US20140288245A1 (en) * 2011-11-01 2014-09-25 Dow Corning Corporation High Glass Transition Temperature Resin Formulations
US8987388B2 (en) * 2011-11-01 2015-03-24 Dow Corning Corporation High glass transition temperature resin formulations
US20150014032A1 (en) * 2012-01-31 2015-01-15 Mitsubishi Gas Chemical Company, Inc. Resin composition for printed wiring board material, and prepreg, resin sheet, metal foil clad laminate, and printed wiring board using same
US9351397B2 (en) * 2012-01-31 2016-05-24 Mitsubishi Gas Chemical Company, Inc. Resin composition for printed wiring board material, and prepreg, resin sheet, metal foil clad laminate, and printed wiring board using same
US9902851B2 (en) 2012-10-19 2018-02-27 Mitsubishi Gas Chemical Company, Inc. Resin composition, prepreg, laminate, and printed wiring board
US10030141B2 (en) 2012-10-19 2018-07-24 Mitsubishi Gas Chemical Company, Inc. Resin composition, pre-preg, laminate, metal foil-clad laminate, and printed wiring board
US10178767B2 (en) 2012-11-28 2019-01-08 Mitsubishi Gas Chemical Company, Inc. Resin composition, prepreg, laminate, metallic foil clad laminate, and printed circuit board
US9929319B2 (en) * 2014-06-13 2018-03-27 General Electric Company LED package with red-emitting phosphors
US20150364659A1 (en) * 2014-06-13 2015-12-17 General Electric Company Led package with red-emitting phosphors
EP3339397A1 (en) * 2016-12-21 2018-06-27 Paroc Group Oy Fire-retardant composition and manufacturing process thereof, and insulation product comprising the fire-retardant composition and manufacturing process thereof

Also Published As

Publication number Publication date
EP2612885B1 (en) 2019-07-24
JPWO2012029690A1 (ja) 2013-10-28
CN103080225A (zh) 2013-05-01
US20170073485A1 (en) 2017-03-16
EP2612885A4 (en) 2017-05-10
CN105860436B (zh) 2019-01-18
WO2012029690A1 (ja) 2012-03-08
KR20130141449A (ko) 2013-12-26
EP2612885A1 (en) 2013-07-10
SG10201506152WA (en) 2015-09-29
TWI600700B (zh) 2017-10-01
US9902825B2 (en) 2018-02-27
JP6157121B2 (ja) 2017-07-05
CN105860436A (zh) 2016-08-17
TW201229121A (en) 2012-07-16
SG187208A1 (en) 2013-02-28

Similar Documents

Publication Publication Date Title
US9902825B2 (en) Resin composition, prepreg, and laminated sheet
EP2543687B1 (en) Resin composition, prepreg, and laminated sheet
US10017660B2 (en) Resin composition, and prepreg and laminated sheet using the same
US9512329B2 (en) Resin composition, prepreg, and laminate
US9955573B2 (en) Resin composition, prepreg and laminate
JP5397717B2 (ja) モリブデン化合物粉体、プリプレグ及び積層板
JP5692062B2 (ja) 樹脂溶液の保存方法、並びに、プリプレグ及び積層板の製造方法
US20130089743A1 (en) Resin composition, prepreg, and laminated sheet
JP2009035728A (ja) プリプレグ及び積層板
WO2010098037A1 (ja) プリプレグ及び積層板

Legal Events

Date Code Title Description
AS Assignment

Owner name: MITSUBISHI GAS CHEMICAL COMPANY, INC., JAPAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:KATO, YOSHIHIRO;OGASHIWA, TAKAAKI;TAKAHASHI, HIROSHI;AND OTHERS;SIGNING DATES FROM 20130130 TO 20130204;REEL/FRAME:029781/0965

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION