WO2007086384A1 - 塗布液および塗膜形成方法 - Google Patents

塗布液および塗膜形成方法 Download PDF

Info

Publication number
WO2007086384A1
WO2007086384A1 PCT/JP2007/051008 JP2007051008W WO2007086384A1 WO 2007086384 A1 WO2007086384 A1 WO 2007086384A1 JP 2007051008 W JP2007051008 W JP 2007051008W WO 2007086384 A1 WO2007086384 A1 WO 2007086384A1
Authority
WO
WIPO (PCT)
Prior art keywords
coating
tridecafluorooctane
mass
coating film
solvent
Prior art date
Application number
PCT/JP2007/051008
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
Kenroh Kitamura
Masaaki Tsuzaki
Hidekazu Okamoto
Michiomi Nagase
Original Assignee
Asahi Glass Company, Limited
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 Asahi Glass Company, Limited filed Critical Asahi Glass Company, Limited
Publication of WO2007086384A1 publication Critical patent/WO2007086384A1/ja

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D127/00Coating 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
    • C09D127/02Coating 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
    • C09D127/12Coating 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
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04Coating
    • C08J7/0427Coating with only one layer of a composition containing a polymer binder
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D133/00Coating 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04Homopolymers or copolymers of esters
    • C09D133/14Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • C09D133/16Homopolymers or copolymers of esters containing halogen atoms
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/02Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to macromolecular substances, e.g. rubber
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00Characterised 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 only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2369/00Characterised by the use of polycarbonates; Derivatives of polycarbonates
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2423/00Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers

Definitions

  • the present invention relates to a coating solution and a coating film forming method containing a fluorine-containing polymer, a water / oil repellent, a flux scooping preventive, a lubricant and the like.
  • a solvent for diluting or dispersing a film-forming component such as a fluoropolymer, a water / oil repellent, a flux scooping preventive, a lubricant, etc.
  • a film-forming component such as a fluoropolymer, a water / oil repellent, a flux scooping preventive, a lubricant, etc.
  • R113 1, 2,2-Trifluoroethane
  • R225 dichloropentafluoropropane
  • Fluorine solvents containing perfluorocarbons hereinafter referred to as PFC
  • PFC perfluorocarbons
  • R113 and R225 have an ozone depletion potential, and PFC has a very high global warming potential. Therefore, the production of black fluorocarbons such as R113 is prohibited. Production and importation of 225 fluorocarbons such as R225 will be banned in developed countries in 2020. PFC is regulated by the Kyoto Protocol to prevent global warming.
  • R225 has a large influence on some synthetic resins, so when a coating liquid containing R225 is applied to a synthetic resin substrate, it may be whitened or cracked depending on the type of synthetic resin. Problems arise.
  • Nonafluorine hexane has been proposed as a fluorine-based solvent that does not adversely affect the global environment and has little effect on synthetic resins (Patent Document 1).
  • Patent Document 1 a coating solution containing nonafluorohexane has insufficient spreadability on the surface of the substrate and may cause unevenness in the coating film.
  • Patent Document 1 International Publication No. 2004Z000977 Pamphlet
  • the purpose of the present invention is to uniformly dissolve or disperse various coating film forming components that do not adversely affect the global environment and have little influence on the synthetic resin substrate, and have excellent spreadability to the substrate surface.
  • Another object of the present invention is to provide a coating solution that is excellent in drying properties and a coating film forming method that can form a coating film with less unevenness in a short time without adversely affecting the global environment and synthetic resin base materials.
  • the coating solution of the present invention contains tridecafluorooctane or a tridecafluorooctane of 60% by mass or more and another organic solvent, and a film-forming component. It is characterized by that.
  • the tridecafluorooctane is preferably 1, 1, 1, 2, 2, 3, 3, 4, 4, 5, 5, 6, 6—tridecafluorooctane.
  • Examples of the coating film forming component include a lubricant.
  • a fluorine-containing polymer is mentioned as a coating-film formation component.
  • fluorine-containing polymer examples include a low reflection film forming agent, a low refractive index film forming agent, a water / oil repellent agent, a flux scooping preventive agent, and a chemical resistant protective film forming agent.
  • fluorinated polymer examples include polymers having a fluorinated alicyclic structure in the main chain; polyfluoroalkyl groups or perfluoropolyether groups in the side chain, acrylates, metatalates, maleates, fumarate, styrene, etc. Examples thereof include a polymer or copolymer having a polymer unit based on the fluorine-containing monomer.
  • the content ratio of the coating film forming component is 0.1 to 20% by mass, and it contains tridecafluorooctane or tridecafluorooctane 60% by mass or more and other organic solvent-powered solvent compositions.
  • the ratio is preferably 80 to 99.9% by mass.
  • Other organic solvents include at least one selected from the group consisting of hydrocarbons, alcohols, ketones, halogenated hydrocarbons (excluding tridecafluorooctane), ethers and esters. Some organic solvents are mentioned.
  • the coating film forming method of the present invention is characterized in that the coating liquid of the present invention is applied to a substrate and the solvent is evaporated.
  • a synthetic resin substrate is preferably used as the substrate.
  • acrylic resin or polycarbonate As the synthetic resin, low chemical resistance, acrylic resin or polycarbonate can be used.
  • the coating solution of the present invention uniformly dissolves or disperses various coating film-forming components that do not adversely affect the global environment and have little effect on the synthetic resin substrate, and can spread to the substrate surface. Excellent and dryness.
  • a soot coating film with less unevenness can be formed in a short time without adversely affecting the global environment and the synthetic resin substrate.
  • the compound represented by the formula (1) is referred to as a compound (1).
  • the coating liquid of the present invention contains a solvent containing tridecafluorooctane and a coating film forming component.
  • the coating solution may be a solution in which a coating film forming component is dissolved in a solvent, or may be a suspension in which a coating film forming component is dispersed in a solvent.
  • a solvent composition consisting of tridecafluorooctane; or tridecafluorooctane 60% by mass or more and another organic solvent is used as a solvent.
  • Tridecafluorooctane means a compound represented by the molecular formula C F H.
  • Mouth octane has no adverse effects on the global environment, has little effect on synthetic resin substrates, has excellent solubility or dispersibility of various film-forming components, has excellent wettability to substrate surfaces, and has good volatility It has the advantage of being! [0014] As tridecafluorooctane, 1, 1, 1, 2, 2, 3, 3, 4, 4, 5 because of its particularly excellent solubility and dispersibility of various film-forming components, , 5, 6, 6 Tridecafluororeoctane, that is, CF (CF) CH CH (hereinafter referred to as HFC-76-13) is preferable.
  • Tridecafluorooctane can be used alone or as a mixture of two or more.
  • the solvent composition may contain another organic solvent excluding tridecafluorooctane depending on the purpose.
  • another organic solvent excluding tridecafluorooctane depending on the purpose.
  • other organic solvents may be further contained.
  • the amount of the other organic solvent is less than 40% by mass of the solvent composition (100% by mass), more preferably 20% by mass or less, and further preferably 10% by mass or less.
  • the lower limit of the amount of the other organic solvent is the minimum amount that can achieve the purpose of adding the other organic solvent.
  • the lower limit of the amount of the other organic solvent is usually 0.1% by mass in the solvent composition (100% by mass).
  • an azeotropic composition exists in the solvent composition, it is preferably used in the azeotropic composition.
  • organic solvents are selected from the group consisting of hydrocarbons, alcohols, ketones, halogenated hydrocarbons (excluding tridecafluorooctane), ethers and esters. At least one of them.
  • Preferred examples of the hydrocarbons are linear or cyclic saturated or unsaturated hydrocarbons having 5 to 15 carbon atoms.
  • Preferred examples thereof include n-pentane, 2-methylbutane, n-hexane, 2-methylpentane, 2,2 dimethylbutane, 2,3 dimethylbutane, n-heptane, 2-methylhexane, 3-methylhexane, 2,4 dimethylpentane, n-octane, 2-methylheptane, 3 methylheptane, 4 Methylheptane, 2,2 Dimethylhexane, 2,5 Dimethylhexane, 3,3 Dimethylhexane, 2-Methyl-3 ethylpentane, 3-Methanole 3 Ethenorepentane, 2, 3, 3 Trimethinolepentane, 2, 3 , 4 Trimethinolepentane, 2, 2, 3 Trimethylpentane, 2 Methylheptane,
  • Preferred examples of alcohols are linear or cyclic saturated or unsaturated alcohols having 1 to 16 carbon atoms. Preferred examples thereof include methanol, ethanol, n-propyl alcohol, isopropyl alcohol, and n -butyl.
  • Alcohol sec butyl alcohol, isobutyl alcohol, tert butyl alcohol, 1 pentanol, 2-pentanol, 1-ethyl-1-propanol, 2-methyl-1-butanol, 3-methyl-1-butanol, 3-methyl-2-butanol, neopentyl alcohol, 1 1-hexanol, 2-methyl-1 pentanol, 4-methyl-2 pentanol, 2 ethyl 1-butanol, 1 1-heptanol, 2 heptanol, 3 heptanol, 1-octanol, 2-octanol, 2 ethyl 1-hexanol , 1-nonanol, 3, 5, 5 Trimethylol 1 Monohexanol, 1-Decanol, 1 Undeanol, 1 Dodecanol, Alinorenoreconole, Propanoleginoleanoreconole, Benzenoleanoreconole,
  • ketones linear or cyclic saturated or unsaturated ketones having 3 to 9 carbon atoms are preferable, and preferable examples thereof include acetone, methyl ethyl ketone, 2 pentanone, 3 pentanone, and 2 Xanone, methylisobutylketone, 2-heptanone, 3-heptanone, 4-heptanone, diisoptylketone, mesityloxide, phorone, 2-octanone, cyclohexanone, methylcyclohexanone, isophorone, 2, 4 pentanedione, 2, 5 Hexanedione, diacetone alcohol, and acetophenone.
  • acetone and methyl ethyl ketone are preferable.
  • halogenated hydrocarbons include saturated or unsaturated chlorinated or chlorinated fluorinated hydrocarbons having 1 to 6 carbon atoms.
  • methylene chloride, 1,2-dichloroethylene, and trichloroethylene are preferable.
  • Preferred examples of the ethers are linear or cyclic saturated or unsaturated ethers having 2 to 8 carbon atoms.
  • Preferred examples include ethers such as jetyl ether, dipropyl ether, diisopropenoatenole, dibuty Noreetenore, ethinorevininoreetenore, butinorevininoreether, arsol, phenetole, methylasol, dioxane, furan, methylfuran, tetrahydrofuran and the like.
  • Particularly preferred are jetyl ether, diisopropyl ether, dioxane, and tetrahydrofuran.
  • esters include linear or cyclic saturated or unsaturated esters having 2 to 19 carbon atoms.
  • preferred esters include methyl formate, ethyl formate, propyl formate, butyl formate, and isobutyl formate.
  • Pentyl formate methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, sec butyl acetate, pentyl acetate, methoxybutyl acetate, sec hexyl acetate, 2-ethylbutyl acetate, 2-ethyl hexyl acetate, Cyclohexyl acetate, benzyl acetate, methyl propionate, ethyl propionate, butyl propionate, methyl butyrate, ethyl butyrate, butyl butyrate, isobutyrate isobutyrate, 2-hydroxy-2-methylpropionate, methyl benzoate, benzoate Acid ethyl, propyl benzoate, butyl benzoate, benzoate benzoate , Y Petite Mouth Rataton, Jetyl oxa
  • the coating film forming component is a component for forming a coating film expressing various functions, and examples thereof include a lubricant and a fluorine-containing polymer.
  • Fluoropolymers include low reflective film formers, low refractive index film formers, water and oil repellents, flux scooping preventives or chemical resistance.
  • a protective protective film forming agent for example, a protective protective film forming agent.
  • the film forming component may be in either liquid or solid form.
  • the coating liquid (10 0 mass 0/0) of, preferably 0.01 to 50% by weight instrument 0 05 to 30% by mass is more preferable 0.1 to 20% by mass is particularly preferable.
  • Fluoropolymers used as low-reflective film-forming agents, low-refractive-index film-forming agents, etc. are heavy polymers having a fluorinated aliphatic ring structure in the main chain because of their excellent transparency to the short wavelength region.
  • the solvent containing tridecafluorooctane has excellent solubility or dispersibility with respect to the ring structure-containing fluoropolymer.
  • the main chain has a fluorine-containing aliphatic ring structure means that at least one carbon atom constituting the aliphatic ring is a carbon atom in the carbon chain constituting the main chain, and the carbon constituting the aliphatic ring. It means having a structure in which a fluorine atom or a fluorine-containing group is bonded to at least a part of the elementary atoms.
  • the aliphatic ring may have an ether bond.
  • Examples of the ring structure-containing fluorine-based polymer include a monomer having a polymerizable double bond between carbon atoms constituting the fluorine-containing aliphatic ring or a carbon atom and an aliphatic group constituting the fluorine-containing aliphatic ring.
  • a homopolymer of a monomer having a polymerizable double bond with an exocyclic carbon atom hereinafter these two monomers are referred to as a cyclic monomer
  • the cyclic monomer and other monomers Copolymer with monomer Japanese Examined Patent Publication No.
  • 63-18964 obtained by cyclopolymerization of a monomer having two polymerizable double bonds (hereinafter referred to as “gen-based monomer”) Homopolymers, copolymers of the gen-based monomers and other monomers (JP-A 63-238111, JP-A 63-238115); cyclic monomers and GEN-based polymers Examples include copolymers with monomers.
  • the cyclic monomer and the gen-based monomer are monomers having a fluorine atom, and are preferably highly fluorinated monomers. “Highly fluorinated” means carbon atoms relative to the total number of hydrogen atoms bonded to carbon atoms and fluorine atoms bonded to carbon atoms. This means that the ratio of the number of fluorine atoms bonded to is 80% or more.
  • a perfluoromonomer (a monomer in which the ratio of the number of fluorine atoms bonded to carbon atoms is 100%) is particularly preferable.
  • the cyclic monomer and the gen-based monomer are perhalopolyfluoromonomers in which 1 to 4 fluorine atoms of the perfluoromonomer (however, the number of total fluorine atoms is 1Z2 or less) are substituted with chlorine. Even so.
  • the other monomer to be copolymerized with the cyclic monomer or the gen-based monomer is preferably a perfluorinated monomer or a perhalopolyfluoromonomer.
  • Examples of the cyclic monomer include compounds (1) to (3).
  • X 11 , X 12 , X 21 , X 22 , X 31 , XR U , R 12 , R 21 , R 22 , 1 , R 32 are each a fluorine atom and a perfluoro having 4 or less carbon atoms. It represents a fluoroalkyl group or a perfluorinated alkoxy group having 4 or less carbon atoms.
  • X 11 , X 21 , X 31 , X 32 are preferably fluorine atoms x 12 , X 22 are fluorine atoms,
  • R u , R 12 , R 21 , R 22 , R and R 32 are preferably a fluorine atom or a trifluoromethyl group.
  • the compound (4) is preferred.
  • Q represents a perfluoroalkylene group having 10 or less carbon atoms and optionally having an etheric oxygen atom.
  • the etheric oxygen atom may be present at one end of the perfluoroalkylene group or at both ends, or may be present between the carbon atoms.
  • the number of carbon atoms is preferably 2-6.
  • Has an etheric oxygen atom between one end or carbon atom In the case of a perfluoroalkylene group, the number of carbon atoms is preferably 1 to 4. In the case of a perfluoroalkylene group having an etheric oxygen atom at both ends, the number of carbon atoms is preferably 1 to 3.
  • a polymer having units of the following formulas (41) to (43) is obtained by cyclopolymerization of the compound (4).
  • the carbon atom of the main chain of the polymer obtained by cyclopolymerization of the gen-based monomer is derived from 4 carbon atoms of 2 polymerizable double bonds.
  • gen-based monomer examples include the following compounds.
  • Examples of the other monomer include tetrafluoroethylene, black-mouthed trifluoroethylene, perfluoro (methyl vinyl ether), and the like.
  • a copolymer of a gen-based monomer and a cyclic monomer is preferable.
  • Examples of the method for producing the ring structure-containing fluoropolymer include the methods described in JP-A-4-189880, JP-A-4-226177 and JP-A-11-279504.
  • the ring structure-containing fluoropolymer may have a functional group.
  • the method for introducing a functional group includes (i) a method of polymerizing a functional group-containing cyclic monomer or a functional group-containing gen monomer, and (ii) a method other than the cyclic monomer and the gen monomer.
  • the method (ii) is preferred, and the method (iii) is particularly preferred.
  • the fluorine-containing polymer used as a water / oil repellent and a flux creeping-up preventing agent contains a polyfluoroalkyl group or a perfluoropolyether group in the side chain, such as attalylate, metatalylate, maleate, fumarate, and Polymers or copolymers having polymerized units based on fluorine-containing monomers such as styrene; polyorganosiloxane compounds having a polyfluoroalkyl group in the side chain; phosphate esters having a polyfluoroalkyl group , Fatty acid ester or urethane compound.
  • a polyfluoroalkyl group or a perfluoropolyether group in the side chain such as attalylate, metatalylate, maleate, fumarate, and Polymers or copolymers having polymerized units based on fluorine-containing monomers such as styrene; polyorganosiloxane compounds having a polyflu
  • lubricant examples include a fluorine-based lubricant, a silicon-based lubricant, and a solid lubricant.
  • Solvents containing tridecafluorooctane have excellent solubility or dispersibility in these lubricants.
  • fluorinated lubricant examples include fluorinated oil and fluorinated grease.
  • silicon-based lubricant examples include silicon oil and silicon grease.
  • solid lubricant examples include polytetrafluoroethylene powder, graphite, and molybdenum disulfide powder.
  • fluorinated oil examples include perfluoropolyethers, and perfluoropolyethers having the structures of the following formulas (5) to (7) are preferred.
  • n, p, q and r each represent an integer of 0 or 1 or more.
  • Examples of the perfluoropolyether having the structure of the formula (5) include demnum manufactured by Daikin Industries, Ltd.
  • Examples of the perfluoropolyether having the structure of the formula (7) include fomblin made of solbaine.
  • the terminal group of the perfluoropolyether includes a hydroxyl group, -CH OH, carbo
  • alkyl group having 1 to 20 carbon atoms, alkyl group, aryl group, ether group, ester group, hydroxyl group salt, sulfonic acid group salt, carboxyl group salt, piperonyl group salt, etc. Is mentioned.
  • perfluoropolyether having a hydroxyl group at the terminal is preferred.
  • compound (5-1) (Demkin manufactured by Daikin Industries, Ltd.), compound (6— 1) (Cryt Tutus manufactured by DuPont) and Compound (7-1) (Vombrin Z—DOL manufactured by Solvaine).
  • n, p and q each represent an integer of 1 or more.
  • the solubility or dispersibility of various coating film forming components that do not adversely affect the global environment and have little influence on the base material made of synthetic resin.
  • Various coatings that do not adversely affect the global environment and have little influence on the base made of synthetic resin because they use a solvent containing tridecafluorooctane, which has excellent wettability to the substrate surface and good volatility.
  • the forming components are uniformly dissolved or dispersed, have excellent spreadability on the substrate surface, and have excellent drying properties.
  • the coating film forming method of the present invention is a method of applying the coating liquid of the present invention to a substrate and evaporating the solvent.
  • the coating film formed by the coating film forming method of the present invention may be a solid film or a liquid film.
  • Examples of the substrate include a metal substrate, a synthetic resin substrate, a glass substrate, and a ceramic substrate. Since the coating liquid of the present invention has little influence on the synthetic resin, it is suitable for a synthetic resin substrate. In addition, since the coating liquid of the present invention has a small viscosity and surface tension, it can be applied thinly and uniformly even on a metal substrate or the like.
  • acrylic resin or polycarbonate can also be used. Forces that cause problems such as cracking and whitening depending on the type of solvent are used for talyl resin and polycarbonate. These problems do not occur when the coating solution of the present invention is used.
  • Examples of the coating method include known methods such as a dipping method and a spin coating method using a spinner.
  • the coating film forming method will be described by taking the dipping method as an example.
  • the substrate is immersed in the coating solution at an appropriate rate, and after maintaining an appropriate immersion time, the substrate is pulled up at an appropriate rate.
  • a coating film comprising a coating film forming component can be formed on the substrate.
  • the thickness of the coating film can be adjusted by coating conditions, coating solution concentration, drying conditions, and the like.
  • Solvents containing HFC-76-13 shown in Examples 1 to 7 in Table 1 are mixed with fluorinated oils having a perfluoroalkyl group (Solvaine, Fomblin Z-DOL) as lubricants. Seven coating solutions (solutions) with an oil content of 0.5% by mass were prepared. did.
  • dryingability was expressed as follows: ⁇ ; immediately dried, ⁇ ; dried within 10 minutes, ⁇ ; dried within 1 hour, X;
  • the numerical value in parentheses in the solvent column indicates the mixing ratio (mass basis) of the two solvents.
  • Solvents containing HFC-76-13 shown in Examples 8 to 14 in Table 2 are mixed with silicone oil (KF-96, manufactured by Shin-Etsu Chemical Co., Ltd.) that also has a polyalkylsiloxane power as a lubricant. Seven coating solutions (solutions) having a content ratio of 0.01% by mass were prepared. Each coating solution was applied to the surface of a stainless steel plate, and the solvent was air-dried to form a lubricant coating on the surface of the stainless steel plate. The drying property of the solvent and the state of the obtained coating film were observed with the naked eye. The results are shown in Table 2. [0056] Evaluation methods of "coating state” and "dryability" in Table 2 were the same as in Examples 1-7.
  • the numerical value in parentheses in the solvent column indicates the mixing ratio (mass basis) of the two solvents.
  • Solvents containing HFC-76-13 shown in Examples 15 to 21 in Table 3 are lubricants, each having a particle size of 0.1 to: LOO ⁇ m polytetrafluoroethylene powder and perfluoropoly
  • Six types of coating liquids (suspensions) with a fluorine lubricant content of 2% by mass were prepared by mixing with a fluorine lubricant composed of ether oil.
  • the numerical value in parentheses in the solvent column indicates the mixing ratio (mass basis) of the two solvents.
  • Acrylic resin and polycarbonate were immersed in a solvent containing HFC-76-13 shown in Examples 22 to 24 in Table 4 for 24 hours at room temperature, and then changes in the appearance of the extracted resin were observed. The results are shown in Table 4.
  • Appearance was evaluated as follows: A: No change, ⁇ : Some whitening or dissolution was observed, X: Whitening, cracking or dissolution was observed.
  • the numerical value in parentheses in the solvent column indicates the mixing ratio (mass basis) of the two solvents.
  • the HFC-76-13 shown in Example 26 of Table 5 contains a fluorinated aliphatic ring structure in the main chain.
  • One fluoropolymer (Cytop-CTX, manufactured by Asahi Glass Co., Ltd.) was mixed, and the dissolution state was observed with the naked eye to evaluate the solubility. Table 5 shows the evaluation results.
  • Example 26 The same test as in Example 26 was performed using R225 shown in Table 5 and fluorinated ether solvent shown in Example 28 (manufactured by Sumitomo 3EM, Novec TM HFE-7100) to evaluate the solubility. The results are shown in Table 5.
  • the value of “solubility” in Table 5 is the solubility of the fluoropolymer when mixed with a solvent at 25 ° C., and is a ratio to the total amount of the mixed solution.
  • Example 6 in Table 6 29% HFC—76—13%, 5% by mass of fluorinated oil with perfluoroalkyl group as lubricant (fombrin Z—DOL) The mixture was coated on a polyethylene terephthalate film tilted at 30 degrees, and the spreadability of the fluorine-based oil was measured. Table 6 shows the evaluation results.
  • Evaluation of the "spread” is calculated by measuring the area of spread fluorine oil, ⁇ ; 10cm 2 or more wanted wide, ⁇ ; is a 10cm less than 2 spread to 5cm 2 or more, X; to less than 5cm 2 It was only spread.
  • Example 30 Tests similar to Example 29 using nonafluo oral hexane (Asahi Glass Co., Ltd., Asahi Clin AC-4000) shown in Example 30 of Table 6 and R225 (Asahi Glass Co., Ltd., Asahi Clin AK-225) shown in Example 31. The spreadability was evaluated. The results are shown in Table 6.
  • HFC-76 having a polymer-based fluorine-based water / oil repellent containing a repeating unit based on a monomer having a polyfluoroalkyl group synthesized by the method described in the examples of JP-A-2005-336234 is 0.5% by mass.
  • the obtained coating solution was sprayed onto a polyamide cloth, which was a test cloth, the test cloth was dried in less than 1 minute to obtain a carved cloth.
  • the water-repellent test of JIS L1092 was performed on the obtained woven fabric, and it showed a 5th grade and showed no stain residue.
  • the coating liquid of the present invention is excellent in solubility or dispersibility, drying property, and spreadability, as is apparent from Examples, and is formed using the coating liquid. No unevenness or the like is observed on the coating film.
  • the coating solution of the present invention [applicable HFC-76-13 ⁇ , conventional R113, R225, PFC, nonafluo-hexane] has an appropriate solubility of coating film forming components, metal, Do not adversely affect plastics and elastomeric base materials.
  • the coating liquid of the present invention can be applied to predetermined parts of equipment and substrates in the manufacture of various equipment and substrates.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Paints Or Removers (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
PCT/JP2007/051008 2006-01-26 2007-01-23 塗布液および塗膜形成方法 WO2007086384A1 (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006017154A JP2009091373A (ja) 2006-01-26 2006-01-26 塗布液および塗膜形成方法
JP2006-017154 2006-01-26

Publications (1)

Publication Number Publication Date
WO2007086384A1 true WO2007086384A1 (ja) 2007-08-02

Family

ID=38309174

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2007/051008 WO2007086384A1 (ja) 2006-01-26 2007-01-23 塗布液および塗膜形成方法

Country Status (3)

Country Link
JP (1) JP2009091373A (zh)
TW (1) TW200740931A (zh)
WO (1) WO2007086384A1 (zh)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107849500B (zh) * 2015-07-27 2020-11-06 Agc株式会社 溶剂组合物、清洗方法、涂膜的形成方法、热传导介质以及热循环系统

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06145080A (ja) * 1992-07-01 1994-05-24 Asahi Glass Co Ltd 混合溶剤組成物
JPH06322213A (ja) * 1993-05-11 1994-11-22 Asahi Glass Co Ltd 撥水撥油性組成物及びそれをコートした物品
JPH07224242A (ja) * 1993-12-15 1995-08-22 Asahi Glass Co Ltd コーティング用含フッ素重合体組成物
JPH11209685A (ja) * 1998-01-27 1999-08-03 Asahi Glass Co Ltd 光学物品用コーティング組成物
JP2002188047A (ja) * 2000-12-21 2002-07-05 Texas Instr Japan Ltd コーティング用組成物およびその製造方法
WO2004000977A1 (ja) * 2002-06-20 2003-12-31 Asahi Glass Company, Limited 潤滑剤溶液、および潤滑剤の塗布方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06145080A (ja) * 1992-07-01 1994-05-24 Asahi Glass Co Ltd 混合溶剤組成物
JPH06322213A (ja) * 1993-05-11 1994-11-22 Asahi Glass Co Ltd 撥水撥油性組成物及びそれをコートした物品
JPH07224242A (ja) * 1993-12-15 1995-08-22 Asahi Glass Co Ltd コーティング用含フッ素重合体組成物
JPH11209685A (ja) * 1998-01-27 1999-08-03 Asahi Glass Co Ltd 光学物品用コーティング組成物
JP2002188047A (ja) * 2000-12-21 2002-07-05 Texas Instr Japan Ltd コーティング用組成物およびその製造方法
WO2004000977A1 (ja) * 2002-06-20 2003-12-31 Asahi Glass Company, Limited 潤滑剤溶液、および潤滑剤の塗布方法

Also Published As

Publication number Publication date
TW200740931A (en) 2007-11-01
JP2009091373A (ja) 2009-04-30

Similar Documents

Publication Publication Date Title
EP1311637B1 (en) Fluoroalkyl (meth)acrylate copolymer coating compositions
TWI831741B (zh) 含氟醚組成物、塗佈液及物品
TWI565719B (zh) Fluorine-containing copolymers, and oil-repellent and / or aqueous-based coating agents
US20050197408A1 (en) Perfluoropolyether derivative
JPH0867888A (ja) 減摩性組成物及び減摩方法
EP1341895A2 (en) Solvent compositions
AU2002227915A1 (en) Solvent compositions
WO2017200105A1 (ja) フッ素含有共重合体
JP2023123689A (ja) ポリテトラフルオロエチレン水性分散液
US6461998B2 (en) Lubricant compositions based on PTFE
JP2019094400A (ja) 滑油性表面処理組成物、その滑油性表面処理組成物を乾燥してなる被膜を有する部材およびその部材が用いられた設備
JP4867138B2 (ja) 溶剤型塗料組成物
JP2019094398A (ja) 滑油性表面処理組成物、その滑油性表面処理組成物を乾燥してなる被膜を有する部材およびその部材が用いられた設備
JP2008519132A (ja) テロマー含有フルオロポリマーコーティング
WO2007086384A1 (ja) 塗布液および塗膜形成方法
CN107207981B (zh) 润滑剂溶液以及具有润滑剂涂膜的物品的制造方法
JP2011063709A (ja) 離型剤
JP2008038108A (ja) フッ素系組成物
JP7265212B2 (ja) 表面処理剤
JPWO2015186798A1 (ja) ポリテトラフルオロエチレン粉末
JP4427176B2 (ja) 離型剤組成物
JPH02138396A (ja) パーフルオロ化共重合体混合物グリース
TWI301507B (zh)
JP2018070832A (ja) 組成物、コーティング液および物品
JP2017155200A (ja) 乾性潤滑被膜形成用エアゾール組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 07707259

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP