WO2020171193A1 - Composition de revêtement au caoutchouc fluoré et article revêtu - Google Patents

Composition de revêtement au caoutchouc fluoré et article revêtu Download PDF

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Publication number
WO2020171193A1
WO2020171193A1 PCT/JP2020/006979 JP2020006979W WO2020171193A1 WO 2020171193 A1 WO2020171193 A1 WO 2020171193A1 JP 2020006979 W JP2020006979 W JP 2020006979W WO 2020171193 A1 WO2020171193 A1 WO 2020171193A1
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Prior art keywords
coating composition
fluororubber
mass
parts
amino group
Prior art date
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PCT/JP2020/006979
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English (en)
Japanese (ja)
Inventor
大輔 三瓶
智洋 城丸
中谷　安利
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ダイキン工業株式会社
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Priority to JP2021502168A priority Critical patent/JPWO2020171193A1/ja
Priority to CN202080014673.6A priority patent/CN113490593A/zh
Priority to KR1020217029595A priority patent/KR20210126711A/ko
Publication of WO2020171193A1 publication Critical patent/WO2020171193A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D115/00—Coating compositions based on rubber derivatives
    • C09D115/02—Rubber derivatives containing halogen
    • 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
    • B32B15/082—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 vinyl resins; comprising acrylic 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
    • B32B25/00—Layered products comprising a layer of natural or synthetic rubber
    • B32B25/04—Layered products comprising a layer of natural or synthetic rubber comprising rubber as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D127/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
    • C09D127/02—Coating compositions based on 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; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D127/12—Coating compositions based on 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; Coating compositions based on 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
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
    • F16J—PISTONS; CYLINDERS; SEALINGS
    • F16J15/00—Sealings
    • F16J15/02—Sealings between relatively-stationary surfaces
    • F16J15/06—Sealings between relatively-stationary surfaces with solid packing compressed between sealing surfaces
    • F16J15/10—Sealings between relatively-stationary surfaces with solid packing compressed between sealing surfaces with non-metallic packing

Definitions

  • the present disclosure relates to fluororubber coating compositions and coated articles.
  • Fluorine rubber is used not only for molded products but also for coating, utilizing its excellent heat resistance, oil resistance, solvent resistance, and chemical resistance.
  • the latter includes, for example, woven fabrics, fibers, metals, plastics, It is widely used as an industrial material by coating or impregnating rubber or other various base materials.
  • Patent Document 1 describes a coating material containing fluororubber, a polyol-based vulcanizing agent, 15 parts by weight of an amino group-containing metal compound, 100 parts by weight of fluororubber, methyl isobutyl ketone and the like.
  • Patent Document 2 describes a coating material containing fluororubber, a polyol-based vulcanizing agent, propylene glycol diacetate (thickener), methyl isobutyl ketone (good solvent), isoparaffin-based solvent (defoaming organic liquid), and the like. There is.
  • An object of the present disclosure is to provide a coating composition that gives a coating film that is less likely to drop from a substrate and has a small compression set, and a coated article provided with such a coating film.
  • the present disclosure includes a fluororubber, a polyol-based vulcanizing agent, an amino group-containing metal compound and an organic solvent
  • the present invention relates to a fluororubber coating composition comprising 100 parts by mass of the fluororubber and 0.1 to 4.99 parts by mass in total of the polyol-based vulcanizing agent and the amino group-containing metal compound.
  • the mass ratio of the polyol-based vulcanizing agent to the amino group-containing metal compound is preferably 1.0:0.1 to 1.0:1.2.
  • the metal of the amino group-containing metal compound is preferably at least one selected from the group consisting of Si, Al, Ti and Zr.
  • the polyol-based vulcanizing agent is 0.1 to 3 parts by mass and the amino group-containing metal compound is 0.1 to 2 parts by mass with respect to 100 parts by mass of the fluororubber.
  • the fluororubber coating composition preferably further contains a stabilizer.
  • the stabilizer is preferably an orthoester compound.
  • the fluororubber coating composition preferably further contains a surface modifier.
  • the fluororubber coating composition preferably further contains an antifoaming agent.
  • the present disclosure includes a metal plate,
  • the present invention also relates to a coated article having a coating film formed from the fluororubber coating composition provided on one side or both sides of the metal plate.
  • the coated article is preferably a fluororubber coated gasket material.
  • a coating composition that gives a coating film that is less likely to drop from the substrate and has a small compression set, and a coated article provided with such a coating film.
  • the present disclosure contains a fluororubber, a polyol-based vulcanizing agent, an amino group-containing metal compound and an organic solvent, and the total amount of the polyol-based vulcanizing agent and the amino group-containing metal compound is 0 with respect to 100 parts by mass of the fluororubber.
  • the present invention relates to a fluororubber coating composition containing 1 to 4.99 parts by mass. Since the fluororubber coating composition of the present disclosure contains the above-mentioned components, it is possible to provide a coating film that is unlikely to drop off from the base material (the coating film is unlikely to set) and that has a small compression set. Therefore, when the above coating composition is applied to a sealing material, excellent sealing properties can be obtained.
  • the coating composition of the present disclosure is also excellent in coating stability.
  • fluororubber examples include vinylidene fluoride [VdF] fluorororubber, tetrafluoroethylene [TFE]/propylene [Pr] fluorororubber, TFE/Pr/VdF fluororubber, ethylene [Et]/hexafluoropropylene [HFP]. ] Fluorine rubber, Et/HFP/VdF type fluorinated rubber, Et/HFP/TFE type fluorinated rubber, fluorosilicone type fluorinated rubber, fluorophosphazene type fluorinated rubber and the like. Of these, VdF fluororubber is preferable.
  • the fluororubber may be used alone or in combination of two or more.
  • VdF fluororubber examples include VdF/HFP copolymer, VdF/TFE/HFP copolymer, VdF/chlorotrifluoroethylene [CTFE] copolymer, VdF/CTFE/TFE copolymer, VdF/perfluoro.
  • CTFE chlorotrifluoroethylene
  • a vulcanizing agent usually used for polyol-vulcanized fluorororubber can be used.
  • the polyol-based vulcanizing agent include compounds having at least two hydroxyl groups, particularly phenolic hydroxyl groups, in the molecule and having vulcanization performance, and the compound may be a polymer compound. ..
  • polyol-based vulcanizing agent examples include, among others, phenol derivatives such as bisphenol A, bisphenol AF, hydroquinone and salts thereof; polyhydroxy compounds having two or more enol type hydroxyl groups in the molecule such as phenol resin and salts thereof. Compounds represented by the formula: R f 1 (CH 2 OH) 2 (R f 1 represents a perfluoroalkyl polyether group) are preferable.
  • any of the commercially available polyol-based vulcanizing agents for fluororubber can be used.
  • the above polyol-based vulcanizing agents may be used alone or in combination of two or more.
  • the polyol-based vulcanizing agent is preferably used in an amount of 0.1 to 3 parts by mass based on 100 parts by mass of the fluororubber.
  • a more preferred lower limit is 0.5 parts by mass and a more preferred upper limit is 2.5 parts by mass.
  • a vulcanization aid can be used to accelerate vulcanization.
  • the vulcanization aid include alkyl and aralkyl quaternary ammonium salts; quaternary ammonium salts such as quaternary 1,8-diaza-bicyclo[5.4.0]-7-undecenium salt; tertiary amines.
  • a quaternary phosphonium salt and the like can be mentioned.
  • the amount used is, for example, 0 to 10 parts by mass with respect to 100 parts by mass of the fluororubber.
  • the preferred lower limit is 0.1 parts by mass, the more preferred lower limit is 0.3 parts by mass, and the preferred upper limit is 5 parts by mass.
  • the amino group-containing metal compound is preferably an amino group-containing metal compound containing at least one metal selected from the group consisting of Si, Al, Ti and Zr.
  • Preferred amino group-containing metal compounds include amino group-containing silane coupling agents, amino group-containing aluminum coupling agents, amino group-containing titanium coupling agents, and amino group-containing zirconium coupling agents.
  • Preferred amino group-containing silane coupling agents are ⁇ -aminopropyltriethoxysilane, N- ⁇ -aminoethyl- ⁇ -aminopropyltrimethoxysilane, N-(trimethoxysilylpropyl)ethylenediamine and N- ⁇ -aminoethyl.
  • Examples include - ⁇ -aminopropylmethyldimethoxysilane, ⁇ -ureidopropyltriethoxysilane, ⁇ -aminoethyl- ⁇ -aminoethyl- ⁇ -aminopropyltrimethoxysilane and the like.
  • the amino group-containing metal compound may be used alone or in combination of two or more.
  • the amino group-containing metal compound is preferably used in an amount of 0.1 to 2 parts by mass with respect to 100 parts by mass of the fluororubber.
  • a more preferred lower limit is 0.5 parts by mass and a more preferred upper limit is 1.5 parts by mass.
  • the coating composition of the present disclosure contains 0.1 to 4.99 parts by mass in total of the polyol-based vulcanizing agent and the amino group-containing metal compound with respect to 100 parts by mass of the fluororubber.
  • the total amount of the polyol-based vulcanizing agent and the amino group-containing metal compound is preferably 1 part by mass or more, more preferably 2 parts by mass or more, based on 100 parts by mass of the fluororubber. It is more preferably 2 parts by mass or more. Further, it is preferably 4.5 parts by mass or less, and more preferably 4 parts by mass or less.
  • the mass ratio between the polyol-based vulcanizing agent and the amino group-containing metal compound is 1.0:0.1 to 1.0:1.2. Is preferred. When the above mass ratio is within the above range, a coating film that is more unlikely to drop from the substrate and has a smaller compression set is obtained.
  • the mass ratio is more preferably 1.0:0.2 to 1.0:1.0, further preferably 1.0:0.5 to 1.0:0.9.
  • the coating composition of the present disclosure contains an organic solvent.
  • the coating composition of the present disclosure may be a solvent-based coating.
  • the organic solvent is not particularly limited, and examples thereof include ketones such as methyl ethyl ketone [MEK], methyl isobutyl ketone [MIBK], diisobutyl ketone [DIBK], diacetone alcohol, cyclohexanone, and isophorone, and esters such as butyl acetate and isopentyl acetate. It is possible to use ethers such as diethylene glycol dimethyl ether, hydrocarbons such as toluene and xylene, and amides such as N,N-dimethylacetamide and N-methyl-2-pyrrolidone.
  • the coating composition of the present disclosure may use only one type of the above organic solvent, or may use two or more types of organic solvents. The blending amount of the organic solvent can be appropriately adjusted according to the type of fluororubber blended in the coating composition
  • the coating composition of the present disclosure preferably further contains a stabilizer.
  • a stabilizer This makes the paint more excellent in stability.
  • the stabilizer include orthoformate ester, orthocarbonate ester, cyclic orthoester, lactone acetal, trimethyl orthoformate ester, triethyl orthoformate ester, trimethyl orthoacetate ester, triethyl orthoacetate ester, trimethyl orthocarbonate ester, and triethyl orthocarbonate ester.
  • Orthoester compounds such as orthocarbonic acid tetramethyl ester and orthocarbonic acid tetraethyl ester; organic acids such as monocarboxylic acid (formic acid, acetic acid, propionic acid, etc.) and dicarboxylic acid (oxalic acid, malonic acid, succinic acid, etc.)
  • organic acids such as monocarboxylic acid (formic acid, acetic acid, propionic acid, etc.) and dicarboxylic acid (oxalic acid, malonic acid, succinic acid, etc.)
  • orthoester compounds are preferable, and orthoacetate compounds are more preferable.
  • the coating composition of the present disclosure may use only one of the above stabilizers, or may use two or more types of stabilizers.
  • the stabilizer is preferably used in an amount of 1 to 8 parts by mass based on 100 parts by mass of the fluororubber. A more preferred lower limit is 2 parts by mass and a more preferred upper limit is 6 parts by mass.
  • the coating composition of the present disclosure preferably further contains a surface conditioner.
  • the surface modifier include siloxane compounds, acrylic copolymers, methacrylic copolymers and the like. Of these, acrylic copolymers are preferable.
  • the surface conditioner is preferably used in an amount of 0.01 to 1 part by mass with respect to 100 parts by mass of the fluororubber.
  • a more preferred lower limit is 0.02 part by mass, and a more preferred upper limit is 0.5 part by mass.
  • the coating composition of the present disclosure preferably further contains an antifoaming agent.
  • an antifoaming agent examples include a silicone defoaming agent and a polymer defoaming agent. Of these, polymer antifoaming agents are preferable.
  • the defoaming agent is preferably used in an amount of 0.05 to 4 parts by mass with respect to 100 parts by mass of the fluororubber.
  • a more preferred lower limit is 0.1 part by mass
  • a more preferred upper limit is 3 parts by mass
  • a still more preferred upper limit is 2 parts by mass.
  • the coating composition of the present disclosure preferably contains both the above surface modifier and the above defoaming agent. As a result, excellent defoaming properties can be achieved even if the amounts of these components added are small. Further, it is possible to obtain a coating film having excellent interlayer adhesion (particularly, adhesion with the upper layer).
  • the mass ratio of the surface conditioner and the defoamer is preferably 1/20 to 1/50, more preferably 1/30 to 1/40.
  • various additives such as fillers and colorants can be added to the coating composition of the present disclosure.
  • the filler include carbon black, white carbon, calcium carbonate, barium sulfate, talc, calcium silicate and the like.
  • the colorant include inorganic pigments and complex oxide pigments.
  • a coating film can be formed by applying the coating composition of the present disclosure to a substrate and drying.
  • the coating composition of the present disclosure may be applied directly to a substrate, or may be applied via another layer such as a primer.
  • the coating composition can be applied by known coating methods such as brush coating, spray coating, dip coating, flow coating, dispenser coating, and screen coating.
  • curing may be performed if necessary.
  • the curing may be performed for each layer or may be performed for a plurality of layers collectively. Further, the curing may be performed simultaneously with the drying.
  • the drying and curing conditions can be appropriately set according to the type of the coating composition of the present disclosure and the like.
  • a substrate to which the coating composition of the present disclosure can be applied a substrate made of metal, concrete, plastic, stone, wood, paper or the like can be used. Of these, a base material made of a metal is preferable.
  • the metal examples include iron; stainless steel; aluminum; copper; brass; titanium; galvanized steel plate plated with aluminum and the like. Of these, stainless steel is preferable.
  • the present disclosure also relates to a coated article comprising a metal plate and a coating film formed from the above-described fluororubber coating composition of the present disclosure, which is provided on one side or both sides of the metal plate. Since the coated article of the present disclosure has the coating film formed from the coating composition of the present disclosure, the coating film is less likely to drop from the substrate (the coating film is less likely to be set) and the compression set is small. Therefore, when the above-mentioned coated article is applied to a sealing material, excellent sealing properties can be obtained.
  • the metal plate it is possible to use a plate made of the metal exemplified as the base material to which the coating composition of the present disclosure can be applied.
  • the coating film formed from the coating composition of the present disclosure is provided on one side or both sides of the metal plate.
  • the coating film may be directly provided on the metal plate or may be provided via another layer such as a primer layer.
  • the coating film preferably has a thickness of 5 to 50 ⁇ m, more preferably 10 to 30 ⁇ m.
  • the coated article of the present disclosure can be produced, for example, by applying the coating composition of the present disclosure on the above metal plate and drying. After coating and drying the coating composition, it may be cured if necessary. When other layers are provided, the curing may be performed for each layer or may be performed for a plurality of layers collectively. Further, the curing may be performed simultaneously with the drying.
  • the drying and curing conditions can be appropriately set according to the type of the coating composition of the present disclosure and the like.
  • the coating composition and the coated article of the present disclosure can be used in a field in which a coating which does not easily fall off from a substrate and has a small compression set is required.
  • the coated article of the present disclosure is a fluororubber coated gasket material.
  • a compound was prepared by kneading 5 parts by mass with an open roll. This compound was mixed with a mixed solvent composed of 240 parts by mass of diisobutyl ketone and 70 parts by mass of isophorone as an organic solvent to obtain a compound solution.
  • a polyol-based vulcanizing agent and 0.5 part by mass of a vulcanization aid are dissolved in 10 parts by mass of ethanol, and 2 parts by mass of an orthoacetic ester compound and 2 parts by mass of an organic acid are used as stabilizers therein.
  • This solution was mixed with the previously prepared compound solution with a disper, and further 0.05 part by mass of an acrylic copolymer as a surface conditioner, 1.8 parts by mass of a polymer defoamer as an antifoaming agent, and amino.
  • a fluororubber coating composition was obtained by mixing 1.2 parts by mass of the group-containing metal compound.
  • Examples 2-6 A fluororubber coating composition was obtained in the same manner as in Example 1 except that the compounding amounts of the surface conditioner and the defoaming agent (or the defoaming organic liquid) were changed as shown in Table 2.
  • the defoaming organic liquid an isoparaffin solvent having a surface tension of 0.026 N ⁇ m ⁇ 1 or less was used.
  • Example 7 A fluororubber coating composition was obtained in the same manner as in Example 1 except that an orthoacetic acid ester compound was not added as a stabilizer.
  • Examples 8 and 9 A fluororubber coating composition was obtained in the same manner as in Example 1 except that the compounding amount of the amino group-containing metal compound was changed as shown in Table 1.
  • Comparative Examples 1 and 2 A fluororubber coating composition was obtained in the same manner as in Example 1 except that the compounding amounts of the polyol-based vulcanizing agent and the amino group-containing metal compound were changed as shown in Table 1.
  • Example 3 The procedure of Example 1 was repeated except that the amounts of the polyol-based vulcanizing agent and the amino group-containing metal compound were changed as shown in Table 1 and that the orthoacetic acid ester-based compound was not added as a stabilizer. A rubber coating composition was obtained.
  • Comparative Example 4 A fluororubber coating composition was obtained in the same manner as in Comparative Example 1 except that an orthoacetic acid ester compound was not added as a stabilizer.
  • ⁇ Coating film (missing)> The coated plate was sandwiched in a jig for measuring compression set without using a spacer and held at 200° C. for 5 hours, and then the presence or absence of a missing coating film edge was visually observed and evaluated. The case where the coating film was not squeezed out or completely missing was evaluated as ⁇ , the case where the coating film was not missing but was squeezed out was evaluated as ⁇ , and the coating film which was missing was evaluated as x. The results are shown in Table 1.
  • Compression set (rate) 100 ⁇ (t 0 ⁇ t 1 )/(t 0 ⁇ t 2 ).
  • t 0 thickness before compression (mm)
  • t 1 Thickness after compression (mm)
  • t 2 Spacer thickness (mm) Those with a compression set of 50% or less were evaluated as O, 51% to 89% as ⁇ , and 90% or more as X.
  • the above-mentioned fluororubber coating composition was sufficiently stirred on a SUS301 plate that had been washed with acetone in advance, and then applied by a screen printing method so that the film thickness of the fired coating film would be 25 ⁇ m.
  • the application was performed 5 times, and the stopwatch immediately after the application was completed in each of the 4 times after the second application. After the start, the time required for the bubbles to completely disappear from the coating film was measured, and the average value of four times was taken as the defoaming time.
  • the screen printer used for coating is a commercially available manual printing system, and a generally commercially available 70 mesh ring pattern screen was used. The results are shown in Table 2.

Abstract

La présente invention concerne une composition de revêtement qui permet d'obtenir un film de revêtement qui n'est pas susceptible de se détacher d'un matériau de base, tout en ayant une faible déformation rémanente après compression. Plus particulièrement, l'invention concerne une composition de revêtement au caoutchouc fluoré qui est caractérisée en ce qu'elle contient un caoutchouc fluoré, un agent de vulcanisation à base de polyol, un composé métallique contenant un groupe amino et un solvant organique, et qui est également caractérisée en ce que l'agent de vulcanisation à base de polyol et le composé métallique contenant un groupe amino sont contenus à une teneur totale de 0,1 à 4,99 parties en masse pour 100 parties en masse du caoutchouc fluoré.
PCT/JP2020/006979 2019-02-21 2020-02-21 Composition de revêtement au caoutchouc fluoré et article revêtu WO2020171193A1 (fr)

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JP2021502168A JPWO2020171193A1 (ja) 2019-02-21 2020-02-21 フッ素ゴム塗料組成物及び塗装物品
CN202080014673.6A CN113490593A (zh) 2019-02-21 2020-02-21 氟橡胶涂料组合物和涂装物品
KR1020217029595A KR20210126711A (ko) 2019-02-21 2020-02-21 불소 고무 도료 조성물 및 도장 물품

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JPH10324840A (ja) * 1997-05-26 1998-12-08 Asahi Glass Co Ltd フッ素ゴム塗料組成物
JP2001181551A (ja) * 1999-10-13 2001-07-03 Toagosei Co Ltd フッ素系塗料用組成物および該組成物の塗装方法
JP2002012813A (ja) * 2000-06-30 2002-01-15 Asahi Glass Co Ltd フッ素ゴム塗料組成物

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