WO2023195485A1 - 組成物および架橋物 - Google Patents

組成物および架橋物 Download PDF

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Publication number
WO2023195485A1
WO2023195485A1 PCT/JP2023/014080 JP2023014080W WO2023195485A1 WO 2023195485 A1 WO2023195485 A1 WO 2023195485A1 JP 2023014080 W JP2023014080 W JP 2023014080W WO 2023195485 A1 WO2023195485 A1 WO 2023195485A1
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WO
WIPO (PCT)
Prior art keywords
group
perfluoroelastomer
composition
crosslinking
polytetrafluoroethylene
Prior art date
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Ceased
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PCT/JP2023/014080
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English (en)
French (fr)
Japanese (ja)
Inventor
明日香 野原
智久 小西
大助 太田
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Daikin Industries Ltd
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Daikin Industries Ltd
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 Daikin Industries Ltd filed Critical Daikin Industries Ltd
Priority to KR1020247036484A priority Critical patent/KR102883772B1/ko
Priority to KR1020257036960A priority patent/KR20250161052A/ko
Priority to CN202511729961.0A priority patent/CN121537728A/zh
Priority to CN202380029375.8A priority patent/CN118922475B/zh
Priority to EP23784769.4A priority patent/EP4506394A4/en
Publication of WO2023195485A1 publication Critical patent/WO2023195485A1/ja
Priority to US18/906,273 priority patent/US20250109289A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
    • C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08L27/18—Homopolymers or copolymers or tetrafluoroethene
    • 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
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F6/00—Post-polymerisation treatments
    • C08F6/14—Treatment of polymer emulsions
    • C08F6/22—Coagulation
    • 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
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • 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
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/12—Powdering or granulating
    • C08J3/16—Powdering or granulating by coagulating dispersions
    • 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
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • C08J3/246—Intercrosslinking of at least two polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
    • C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
    • C09K3/1009—Fluorinated polymers, e.g. PTFE
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/26—Tetrafluoroethene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/26—Tetrafluoroethene
    • C08F214/262—Tetrafluoroethene with fluorinated vinyl ethers
    • 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
    • C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
    • C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • 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
    • C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
    • C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08J2327/18—Homopolymers or copolymers of tetrafluoroethylene
    • 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
    • C08J2427/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
    • C08J2427/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2427/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • 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
    • C08J2427/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
    • C08J2427/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2427/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08J2427/18—Homopolymers or copolymers of tetrafluoroethylene
    • 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
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/22—Mixtures comprising a continuous polymer matrix in which are dispersed crosslinked particles of another polymer
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking

Definitions

  • PTFE with a melt viscosity within the above range, a crosslinked product having excellent plasma resistance and compression set properties can be obtained when the composition is crosslinked. If the melt viscosity of PTFE is too high, the compression set properties of the crosslinked product will not be sufficiently improved, and for example, when the crosslinked product is compressed for a long time at a high temperature of about 300°C, there is a problem that the crosslinked product will collapse due to compression. This may cause the problem that the shape of the crosslinked product is difficult to restore.
  • PTFE whose melt viscosity is too low may not be suitable for use in crosslinked products used at high temperatures (for example, about 300° C.) because it may generate volatile components at high temperatures.
  • the average primary particle size of PTFE is preferably 10 nm to 1000 ⁇ m, more preferably 100 nm or more, even more preferably 200 nm or more, more preferably 100 ⁇ m or less, still more preferably 10 ⁇ m or less, and particularly preferably is 1 ⁇ m or less, particularly preferably 500 nm or less.
  • a modified monomer unit means a part of the molecular structure of PTFE that is derived from a modified monomer, and a whole monomer unit means a part that is derived from all monomers in the molecular structure of PTFE.
  • the content of modified monomer units is a value measured by infrared spectroscopy or NMR (nuclear magnetic resonance).
  • Rf is a group represented by the following formula: CF 3 CF 2 CF 2 -(O-CF(CF 3 )-CF 2 ) n - (In the formula, n represents an integer of 1 to 4).
  • a perfluoroelastomer is a fluoropolymer in which the content of perfluoromonomer units based on all monomer units is 90 mol% or more, preferably 91 mol% or more, and has a glass transition temperature of 20°C or less.
  • a fluoropolymer having a melting peak ( ⁇ H) size of 4.5 J/g or less and further, the concentration of fluorine atoms contained in the fluoropolymer is 71% by mass or more, preferably 71.5% by mass or more. It is a polymer.
  • the above glass transition temperature was determined by obtaining a DSC curve by heating 3 mg of a sample at a rate of 10°C/min using a differential scanning calorimeter (manufactured by Hitachi High-Tech Science Co., Ltd., X-DSC7000). It can be determined as the temperature indicating the midpoint of the two intersections of the extension line of the baseline and the tangent at the inflection point of the DSC curve.
  • CY 1 2 CY 1 (CF 2 ) n -CN
  • Y 1 is each independently a hydrogen atom or a fluorine atom, and n is an integer from 1 to 8)
  • Formula: CF 2 CFCF 2 Rf 8 -CN (In the formula, Rf 8 is -(OCF 2 ) n - or -(OCF(CF 3 )) n -, where n is an integer from 0 to 5)
  • Formula: CF 2 CFCF 2 (OCF(CF 3 )CF 2 ) m (OCH 2 CF 2 CF 2 ) n OCH 2 CF 2 -CN (In the formula, m is an integer from 0 to 5, and n is an integer from 0 to 5.)
  • Formula: CF 2 CFCF 2 (OCH 2 CF 2 CF 2 ) m (OCF(CF 3 )CF 2 ) n OCF(
  • the temperature of each aqueous dispersion when mixing the aqueous dispersion containing the perfluoroelastomer and the aqueous dispersion containing PTFE is preferably 10°C or higher, more preferably 15°C or higher, and even more preferably is 20°C or higher, preferably 60°C or lower, and more preferably 50°C or lower.
  • Methods for co-coagulating the perfluoroelastomer and PTFE in the aqueous dispersion thus obtained include a method of mixing the aqueous dispersion and a coagulant, and a method of freezing.
  • coagulant known coagulants such as acids can be used, such as aluminum salts, calcium salts, or magnesium salts, organic coagulants such as ammonium acetate and ammonium carbonate, and inorganic acid coagulants such as hydrochloric acid. , nitric acid, hydrofluoric acid, sulfuric acid, trifluoroacetic acid, etc.
  • the composition obtained by co-coagulation is washed with water to remove small amounts of impurities such as buffers and salts present in the composition, and then the washed composition is heated in a hot air oven, vacuum dryer, etc. May be dried.
  • the drying temperature is preferably 40°C or higher, more preferably 50°C or higher, even more preferably 60°C or higher, preferably 200°C or lower, more preferably 150°C or lower, and even more preferably The temperature is 100°C or less.
  • Examples of other components include fillers.
  • additives such as processing aids, plasticizers, colorants, etc.
  • processing aids plasticizers, colorants, etc.
  • One or more types of commonly used crosslinking agents and crosslinking aids different from the above may be blended.
  • inorganic nitrides include, but are not limited to, silicon nitride (Si 3 N 4 ), lithium nitride, titanium nitride, aluminum nitride, boron nitride, vanadium nitride, zirconium nitride, and the like.
  • silicon nitride is preferred because nano-sized particles can be supplied.
  • the compound that generates ammonia is preferably a compound that generates ammonia at a temperature of 40 to 330°C.
  • ammonia-generating compound urea or a derivative thereof, or an ammonium salt is preferable, urea or an ammonium salt is more preferable, and urea is even more preferable.
  • the ammonium salt may be an organic ammonium salt or an inorganic ammonium salt. Further, the ammonia-generating compound may be one that reacts with a trace amount of water to generate ammonia.
  • a composition according to the first aspect is provided, wherein the perfluoroelastomer has a cyano group.
  • the average primary particle size of PTFE is determined by the transmittance when 550 nm light is incident on a predetermined cell injected with a PTFE aqueous dispersion with a solid content of 0.15% by mass, and the diameter in a specific direction based on a transmission electron micrograph. After determining the correlation with the calculated number average primary particle diameter, the transmittance measured for the obtained sample was applied to the above correlation (calibration curve method).
  • Comparative example 3 0.9 parts by mass of a crosslinking agent (2,2-bis[3-amino-4-(N-phenylamino)phenyl]hexafluoropropane) was added to 100 parts by mass of the perfluoroelastomer particles prepared in Comparative Example 1 in an open roll. The mixture was kneaded to obtain a crosslinkable elastomer composition. An O-ring was produced from a crosslinkable elastomer composition in the same manner as in Example 1, and the obtained O-ring was evaluated in the same manner. The results are shown in Table 2.
  • a crosslinking agent 2,2-bis[3-amino-4-(N-phenylamino)phenyl]hexafluoropropane

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
PCT/JP2023/014080 2022-04-06 2023-04-05 組成物および架橋物 Ceased WO2023195485A1 (ja)

Priority Applications (6)

Application Number Priority Date Filing Date Title
KR1020247036484A KR102883772B1 (ko) 2022-04-06 2023-04-05 조성물 및 가교물
KR1020257036960A KR20250161052A (ko) 2022-04-06 2023-04-05 조성물 및 가교물
CN202511729961.0A CN121537728A (zh) 2022-04-06 2023-04-05 组合物和交联物
CN202380029375.8A CN118922475B (zh) 2022-04-06 2023-04-05 组合物和交联物
EP23784769.4A EP4506394A4 (en) 2022-04-06 2023-04-05 COMPOSITION AND CROSS-CUT PRODUCT
US18/906,273 US20250109289A1 (en) 2022-04-06 2024-10-04 Composition and cross-linked article

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2022-063403 2022-04-06
JP2022063403A JP7319573B1 (ja) 2022-04-06 2022-04-06 組成物および架橋物

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US18/906,273 Continuation US20250109289A1 (en) 2022-04-06 2024-10-04 Composition and cross-linked article

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WO2023195485A1 true WO2023195485A1 (ja) 2023-10-12

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US (1) US20250109289A1 (https=)
EP (1) EP4506394A4 (https=)
JP (2) JP7319573B1 (https=)
KR (2) KR102883772B1 (https=)
CN (2) CN118922475B (https=)
TW (1) TWI900842B (https=)
WO (1) WO2023195485A1 (https=)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025105257A1 (ja) * 2023-11-15 2025-05-22 ニチアス株式会社 ゴム組成物、含フッ素エラストマーおよびシール材
WO2025225463A1 (ja) * 2024-04-22 2025-10-30 Ａｇｃ株式会社 含フッ素共重合体組成物及びその製造方法、並びにフッ素ゴム物品

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Publication number Priority date Publication date Assignee Title
CN118388949B (zh) * 2024-05-22 2024-12-13 上海芯密科技股份有限公司 一种高白度氟橡胶组合物及其制备方法和应用

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JP2003026811A (ja) 2001-07-23 2003-01-29 Morisei Kako:Kk 封止材用フッ素系組成物およびその製造方法
WO2005019336A1 (ja) * 2003-08-25 2005-03-03 Daikin Industries, Ltd. 成形体及びその製造方法、高周波信号伝送用製品並びに高周波伝送ケーブル
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