WO2016121795A1 - Solution de lubrifiant et procédé pour la fabrication d'article avec film de revêtement lubrifiant - Google Patents

Solution de lubrifiant et procédé pour la fabrication d'article avec film de revêtement lubrifiant Download PDF

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Publication number
WO2016121795A1
WO2016121795A1 PCT/JP2016/052278 JP2016052278W WO2016121795A1 WO 2016121795 A1 WO2016121795 A1 WO 2016121795A1 JP 2016052278 W JP2016052278 W JP 2016052278W WO 2016121795 A1 WO2016121795 A1 WO 2016121795A1
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Prior art keywords
lubricant
solvent
mass
tdce
lubricant solution
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PCT/JP2016/052278
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English (en)
Japanese (ja)
Inventor
宏明 光岡
花田　毅
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旭硝子株式会社
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Priority to CN201680007358.4A priority Critical patent/CN107207981B/zh
Priority to JP2016572087A priority patent/JP6686911B2/ja
Publication of WO2016121795A1 publication Critical patent/WO2016121795A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/50—Lubricating compositions characterised by the base-material being a macromolecular compound containing silicon
    • 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
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • 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
    • C09D7/20—Diluents or solvents
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
    • C10M2229/0415—Siloxanes with specific structure containing aliphatic substituents used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/047—Siloxanes with specific structure containing alkylene oxide groups
    • C10M2229/0475—Siloxanes with specific structure containing alkylene oxide groups used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/052—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing nitrogen
    • C10M2229/0525—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing nitrogen used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/70—Soluble oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/015—Dispersions of solid lubricants
    • C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating

Definitions

  • the present invention relates to a lubricant solution and a method for producing an article with a lubricant coating.
  • an article having a coating film containing a lubricant (hereinafter, also referred to as a lubricant coating film) is obtained by applying a lubricant solution in which a lubricant is dissolved in a solvent to the surface of an object to be coated and then evaporating the solvent.
  • a lubricant solution in which a lubricant is dissolved in a solvent
  • evaporating the solvent Manufactured by forming a lubricant coating on the surface of an object to be coated.
  • chlorofluorocarbons hereinafter referred to as CFCs
  • HCFCs hydrochlorofluorocarbons
  • solvents that do not adversely affect the ozone layer include perfluorocarbons (hereinafter referred to as PFCs), hydrofluorocarbons (hereinafter referred to as HFCs), and hydrofluoroethers (hereinafter referred to as HFEs). Etc. are known.
  • PFCs and HFCs are substances subject to the Kyoto Protocol because of their large global warming potential.
  • PFCs, HFCs, and HFEs have a low solubility as a lubricant, and therefore have a narrow range of application as solvents for lubricants.
  • trans-1,2-dichloroethylene CHCl, hereinafter also referred to as tDCE
  • tDCE trans-1,2-dichloroethylene
  • tDCE is known as a solvent that does not adversely affect the global environment and is excellent in the solubility of the lubricant.
  • tDCE is difficult to use alone because it has a flash point.
  • Patent Document 1 discloses a solvent composed of tDCE and methyl perfluorobutyl ether (CH 3 OCF 2 CF 2 CF 2 CF 3 , hereinafter also referred to as HFE-449s1).
  • HFE-449s1 methyl perfluorobutyl ether
  • the solvent disclosed in Patent Document 1 is useful as a solvent for silicone lubricants.
  • Patent Document 2 discloses a solvent containing tDCE and methyl perfluoroheptene ether (hereinafter also referred to as MPHE).
  • MPHE methyl perfluoroheptene ether
  • the object to be coated with the lubricant coating is a metal such as an injection needle
  • a modified silicone oil, particularly a diamine-modified silicone oil is used as the lubricant because it has excellent adhesion to the metal.
  • the solvents of Patent Documents 1 and 2 dissolve diamine-modified silicone oil, the stability of a solution stored for several days (hereinafter referred to as storage stability) is insufficient. Therefore, the lubricant solution containing the diamine-modified silicone oil and the solvent of Patent Document 1 or 2 has a problem that the cloudiness or the lubricant is separated during storage. And when using the lubricant solution from which white turbidity or the lubricant isolate
  • the diamine-modified silicone oil may be used in combination with a diamine group-containing alkoxysilane that is a crosslinking agent.
  • Patent Document 3 discloses that tDCE and 1,1,2,2-tetrafluoro-1- (2,2,2-trifluoroethoxy) ethane (CF 3 CH 2 OCF 2 CF 2 H (hereinafter also referred to as HFE-347pc-f), and Patent Document 4 disclose a solvent containing tDCE, HFE-347pc-f, and methanol, respectively.
  • Patent Documents 3 and 4 do not describe the use of these disclosed solvents as lubricant solvents.
  • An object of the present invention is to provide a lubricant solution that does not adversely affect the global environment, has excellent storage stability and does not have a flash point, and a method for producing an article with a lubricant coating using the lubricant solution.
  • the present invention provides a lubricant solution and an article with a lubricant coating having the following constitution.
  • a lubricant solution comprising 40 to 70% by mass of HFE-347pc-f and 30 to 60% by mass of 100% by mass of tDCE and HFE-347pc-f in total.
  • a lubricant solution that does not adversely affect the global environment, has excellent storage stability, and does not have a flash point. Furthermore, it is possible to provide a method for producing an article with a lubricant coating, which can safely produce an article having a uniform lubricant coating without adversely affecting the global environment.
  • “Lubricant” means a material used to reduce friction on a contact surface and prevent generation of heat and wear damage when two members move with the surfaces in contact with each other.
  • “Fluorine-based lubricant” means a lubricant having a fluorine atom in the molecule.
  • “Silicone-based lubricant” means a lubricant containing silicone.
  • Silicon oil is a polymer of an organosilicon compound having a siloxane bond (Si—O—Si) as the main skeleton and an organic group such as a methyl group bonded to a silicon atom, so-called silicone, which has a relatively high degree of polymerization.
  • the “diamine-modified silicone oil” means one having a diamine group (—RNHR′NH 2 , where R and R ′ are each a divalent organic group) as part of the organic group of the silicone oil.
  • solvent means that diamine-modified silicone oil can be dissolved by itself or in combination with other solvents, can evaporate at the temperature at which a lubricant film is formed, and does not react with lubricants and additives. Means a liquid compound at room temperature (25 ° C.).
  • Organic solvent that is soluble in tDCE means that the solvent is mixed with tDCE so as to have a desired concentration and stirred at room temperature (25 ° C.) to dissolve evenly without causing two-layer separation or turbidity. An organic solvent that can be produced.
  • No flash point means having no flash point between 23 ° C. and boiling point.
  • Diamine group-containing alkoxysilane means a compound having a diamine group and an alkoxy group bonded to a silicon atom.
  • the lubricant solution of the present invention contains a lubricant (A) and a solvent (B).
  • the lubricant solution may contain an additive (C) in addition to the lubricant (A) and the solvent (B) as required, within a range not impairing the effects of the present invention.
  • the lubricant (A) contains a diamine-modified silicone oil. If necessary, the lubricant (A) may contain other lubricants in a range not impairing the effects of the present invention, in addition to the diamine-modified silicone oil.
  • diamine-modified silicone oil Specific examples of the diamine-modified silicone oil or the lubricant (A) containing the diamine-modified silicone oil include the following.
  • a main component is a copolymer of a diamine group-containing alkylsiloxane and dimethylsiloxane described in JP-B-46-3627.
  • dimethylpolysiloxane side chain or a part of the methyl group at the end is substituted with a diamine group because it is easily available, adsorbs to the metal surface, and is excellent in lubricity.
  • the compound represented by Formula (1) is preferable.
  • each A is independently a methyl group, a hydroxy group, an epoxy group, an alkoxy group (—OR ′′), or a diamine group (—RNHR′NH 2 ), provided that at least one of A One is a diamine group, R and R ′ are each a divalent organic group, and R ′′ is a monovalent organic group.
  • m and n are each an integer of 1 or more.
  • R is preferably an alkylene group, more preferably an alkylene group having 1 to 5 carbon atoms, and particularly preferably an alkylene group having 3 carbon atoms.
  • R ′ is preferably an alkylene group, more preferably an alkylene group having 1 to 5 carbon atoms, and particularly preferably an alkylene group having 2 carbon atoms.
  • R ′′ is preferably an alkyl group, more preferably an alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group.
  • Examples of commercially available diamine-modified silicone oil or lubricant (A) containing diamine-modified silicone oil include the following. “TSF 4702”, “TSF 4703”, “TSF 4704”, “TSF 4705”, “TSF 4706”, “TSF 4707”, “TSF 4708” manufactured by Momentive Performance Materials Japan. “SF8417”, “BY16-849”, “BY16-205”, “FZ-3760”, “BY16-892”, “FZ-3785”, “BY16-872”, “BY16-” manufactured by Toray Dow Corning 893 “,” FZ-3789 “,” MDX4-4159 “.
  • a diamine modified silicone oil may be used individually by 1 type, and may use 2 or more types together.
  • Other lubricants are preferably silicone-based lubricants or fluorine-based lubricants other than diamine-modified silicone oils because of their excellent solubility in tDCE. Other lubricants are appropriately selected according to the required lubrication performance.
  • the other lubricant may be in any form of liquid (oil), semi-solid (grease), and solid.
  • silicone oil dimethyl silicone oil, which is an unmodified silicone oil, or modified silicone oil (excluding diamine-modified silicone oil) is preferable.
  • modified silicone oil hydrogen-modified silicone oil, methylphenyl silicone oil, and cyclic dimethyl silicone oil are preferable.
  • commercially available silicone oils include the following. “KF-96”, “KF-965”, “KF-968”, “KF-99”, “KF-50”, “KF-54”, “HIVAC F-4”, “ “HIVAC F-5", “KF-56A”, “KF-995". “SH200” manufactured by Toray Dow Corning.
  • silicone oil is preferably used as a base oil and a thickener such as metal soap and various additives are blended.
  • a thickener such as metal soap and various additives are blended.
  • commercially available silicone greases include the following. “G-30 Series”, “G-40 Series”, “FG-720 Series”, “G-411”, “G-501”, “G-6500”, “G-330” manufactured by Shin-Etsu Chemical Co., Ltd. , “G-340”, “G-350”, “G-630”.
  • fluorine-based lubricant examples include fluorine oil, fluorine grease, and fluorine-based solid lubricant (polytetrafluoroethylene powder and the like).
  • silicone-based lubricant examples include silicone oil and silicone grease.
  • fluorine-based lubricant and the silicone-based lubricant include fluorosilicone oil which is a modified silicone oil in which a terminal or a side chain is substituted with a fluoroalkyl group.
  • Fluorine oil is preferably a low polymer of perfluoropolyether or chlorotrifluoroethylene.
  • fluorine oils include the following. "Crytox (registered trademark) GPL102” manufactured by DuPont. "Daifloil (registered trademark) # 1", “Daiflooil (registered trademark) # 3", “Daiflooil (registered trademark) # 10", “Daiflooil (registered trademark) # 20", “Daiflooil (registered trademark)” manufactured by Daikin Industries, Ltd. ) # 50 "," Daifloil (registered trademark) # 100 ",” Demnam (registered trademark) S-65 ".
  • Fluorine grease preferably contains fluorine oil as a base oil and is blended with polytetrafluoroethylene powder or other thickener.
  • fluorine greases include the following. "Crytox (registered trademark) Grease 240AC” manufactured by DuPont. "Daifloil (registered trademark) Grease DG-203", “Demnam (registered trademark) L65”, “Demnam (registered trademark) L100", “Demnam (registered trademark) L200” manufactured by Daikin Industries, Ltd. “Sumitec F936” manufactured by Sumiko Lubricant Co., Ltd.
  • fluorosilicone oils examples include the following. “Unidyne (registered trademark) TG-5601” manufactured by Daikin Industries, Ltd. "Moricoat (registered trademark) 3451” and “Moricoat (registered trademark) 3452” manufactured by Toray Dow Corning. “FL-5”, “X-22-821”, “X-22-822”, “FL-100” manufactured by Shin-Etsu Chemical Co., Ltd.
  • a lubricant (A) may be sufficient as the other lubricant contained in a lubricant (A), and 2 or more types may be sufficient as it.
  • the silicone-based lubricant and the fluorine-based lubricant may be used alone or in combination.
  • solvent (B) contains tDCE and HFE-347pc-f. If necessary, the solvent (B) may contain an organic solvent (B1) soluble in tDCE in addition to tDCE and HFE-347pc-f as long as the effects of the present invention are not impaired.
  • the solvent (B) preferably does not contain any other solvent other than tDCE, HFE-347pc-f, and the organic solvent (B1).
  • tDCE Since tDCE is an olefin having a double bond between carbon atoms, it has a short lifetime in the atmosphere and does not adversely affect the global environment. Since tDCE has a boiling point of about 49 ° C., it has excellent drying properties. In addition, since the boiling point is about 49 ° C. even when the liquid is boiled, tDCE is less likely to adversely affect parts that are easily affected by heat such as resin parts. tDCE has a low surface tension and low viscosity and easily evaporates even at room temperature. tDCE is excellent in the solubility of other lubricants. As described above, tDCE has sufficient performance as a solvent in a lubricant solution, except that it has a flash point.
  • tDCE examples include the following. “Trans-LC (registered trademark)” manufactured by Daido Air Products Electronics. “Trans-1,2-dichloroethylene” manufactured by PPG INDUSTRIES INC.
  • HFE-347pc-f has a zero ozone depletion coefficient and a low global warming coefficient.
  • HFE-347pc-f has an excellent drying property because it has a boiling point of about 56 ° C. In addition, even if boiled and vaporized, the boiling point is about 56 ° C., so HFE-347pc-f is less likely to adversely affect parts that are easily affected by heat such as resin parts.
  • HFE-347pc-f has no flash point.
  • HFE-347pc-f has low surface tension and low viscosity and easily evaporates even at room temperature. As described above, HFE-347pc-f has sufficient performance as a solvent in a lubricant solution, except that the solubility of the diamine-modified silicone oil is low.
  • HFE-347pc-f is prepared in the presence of an aprotic polar solvent and a catalyst (alkali metal alkoxide or alkali metal hydroxide) described in WO 2004/108644, for example. It can be produced by a method of reacting fluoroethanol and tetrafluoroethylene.
  • a catalyst alkali metal alkoxide or alkali metal hydroxide
  • HFE-347pc-f examples include the following. “Asahiklin (registered trademark) AE-3000” manufactured by Asahi Glass Co., Ltd.
  • Organic solvent (B1) is an organic solvent soluble in tDCE.
  • the organic solvent (B1) is appropriately selected according to various purposes such as increasing the solubility and adjusting the volatilization rate.
  • organic solvent (B1) examples include hydrocarbons, alcohols, ketones, ethers, esters, chlorocarbons (excluding tDCE), HFCs, HFEs (HFE-347pc-f) soluble in tDCE. ), Hydrofluoroolefins (hereinafter also referred to as HFOs), chlorofluoroolefins (hereinafter also referred to as CFOs), hydrochlorofluoroolefins (HCFOs), and the like.
  • HFOs Hydrofluoroolefins
  • CFOs chlorofluoroolefins
  • HCFOs hydrochlorofluoroolefins
  • hydrocarbons soluble in tDCE hydrocarbons having 5 or more carbon atoms are preferable.
  • the hydrocarbons may be chain hydrocarbons, cyclic hydrocarbons, saturated hydrocarbons, or unsaturated hydrocarbons.
  • hydrocarbons soluble in tDCE 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-methyl-3-ethylpentane, 2,3,3-trimethylpentane, 2,3,4
  • alcohols soluble in tDCE alcohols having 1 to 16 carbon atoms are preferable, and alcohols having 1 to 3 carbon atoms are more preferable because they have an azeotropic composition with tDCE and HFE-347pc-f.
  • the alcohol may be a chain alcohol, may be a cyclic alcohol, may be a saturated alcohol, or may be an unsaturated alcohol.
  • alcohols soluble in tDCE include methanol, ethanol, n-propyl alcohol, isopropyl alcohol, 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-hexanol, 2-methyl-1-pentanol, 4 -Methyl-2-pentanol, 2-ethyl-1-butanol, 1-heptanol, 2-heptanol, 3-heptanol, 1-octanol, 2-octanol, 2-ethyl-1-hexanol, 1-nonanol, 3, 5,5-trimethyl-1-hexanol, -Decanol, 1-undecanol
  • ketones soluble in tDCE ketones having 3 to 9 carbon atoms are preferable.
  • the ketones may be chain ketones, cyclic ketones, saturated ketones, or unsaturated ketones.
  • Ketones soluble in tDCE include acetone, methyl ethyl ketone, 2-pentanone, 3-pentanone, 2-hexanone, methyl isobutyl ketone, 2-heptanone, 3-heptanone, 4-heptanone, diisobutyl ketone, mesityl oxide, phorone.
  • acetone and methyl ethyl ketone are preferable.
  • ethers soluble in tDCE ethers having 2 to 8 carbon atoms are preferable.
  • the ethers may be chain ethers, cyclic ethers, saturated ethers, or unsaturated ethers.
  • Examples of ethers soluble in tDCE include diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, ethyl vinyl ether, butyl vinyl ether, anisole, phenetol, methylanisole, furan, methylfuran, tetrahydrofuran and the like. Among these, diethyl ether, diisopropyl ether, and tetrahydrofuran are preferable.
  • esters having 2 to 19 carbon atoms are preferable.
  • the esters may be chain esters, may be cyclic esters, may be saturated esters, or may be unsaturated esters.
  • Esters soluble in tDCE include methyl formate, ethyl formate, propyl formate, butyl formate, 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-ethylhexyl acetate, cyclohexyl acetate, benzyl acetate, ethyl propionate, ethyl propionate,
  • chlorocarbons soluble in tDCE chlorocarbons having 1 to 3 carbon atoms are preferable.
  • the chlorocarbons may be chain chlorocarbons, cyclic chlorocarbons, saturated chlorocarbons, or unsaturated chlorocarbons. .
  • chlorocarbons soluble in tDCE examples include methylene chloride, 1,1-dichloroethane, 1,2-dichloroethane, 1,1,2-trichloroethane, 1,1,1,2-tetrachloroethane, 1,1,2, 2,2-tetrachloroethane, pentachloroethane, 1,1-dichloroethylene, cis-1,2-dichloroethylene, trichloroethylene, tetrachloroethylene, 1,2-dichloropropane and the like. Of these, methylene chloride is preferred.
  • HFCs soluble in tDCE chain or cyclic HFCs having 4 to 8 carbon atoms are preferable, and HFCs having one or more fluorine atoms in one molecule are more than hydrogen atoms.
  • HFCs soluble in tDCE include 1,1,1,3,3-pentafluorobutane, 1,1,1,2,2,3,4,5,5,5-decafluoropentane, 1,2,2,3,3,4-heptafluorocyclopentane, 1,1,1,2,2,3,3,4,4-nonafluorohexane, 1,1,1,2,2,3 , 3,4,4,5,5,6,6-tridecafluorohexane, 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorooctane Etc.
  • 1,1,1,2,2,3,4,5,5,5-decafluoropentane, 1,1,1,2,2,3,3,4,4-nonafluorohexane, 1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorohexane is preferred.
  • HFEs soluble in tDCE include HFE-449s1, ethyl perfluorobutyl ether, and the like. Among these, HFE-449s1 is preferable.
  • HFOs soluble in tDCE include MPHE, 1,1,1,4,4,4-hexafluoro-2-butene and the like.
  • CFOs soluble in tDCE include 1,1-dichloro-2,3,3,3-tetrafluoro-1-propene (CFO-1214ya).
  • HCFOs soluble in tDCE include cis and trans isomers of 1-chloro-3,3,3-trifluoropropene, 1,1-dichloro-3,3,3-trifluoropropene and the like.
  • the organic solvent (B1) contained in the solvent (B) may be one type or two or more types.
  • the combination of the organic solvents (B1) may be a combination of the same category or a combination of different categories of solvents. Also good.
  • the organic solvent (B1) may be a combination of two kinds of hydrocarbons or a combination of one kind of hydrocarbon and one kind of alcohol.
  • the organic solvent (B1) is more preferably a solvent having no flash point.
  • the organic solvent (B1) having no flash point 1,1,1,2,2,3,4,5,5,5-decafluoropentane, 1,1,1,2,2,3,3 , 4,4-nonafluorohexane, HFCs such as 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorohexane, HFE-449s1, etc. HFEs etc. are mentioned.
  • the solvent (B) is preferably mixed with tDCE and HFE-347pc-f within a range not having a flash point.
  • tDCE and HFE-347pc-f and the organic solvent (B1) form an azeotropic composition, they can be used in the azeotropic composition.
  • the additive (C) is a component other than the lubricant (A) and the solvent (B) in the lubricant solution.
  • the additive (C) include a crosslinking agent, a solvent other than tDCE, HFE-347pc-f, and the organic solvent (B1); other additives than these.
  • crosslinking agent examples include alkoxysilanes or partial condensates (oligomers) thereof.
  • Alkoxysilanes include so-called silane coupling agents such as tetraalkoxysilanes, mono, di, or trialkoxysilanes having alkyl or aryl groups, mono, di, or trialkoxysilanes having reactive functional groups.
  • silane coupling agents such as tetraalkoxysilanes, mono, di, or trialkoxysilanes having alkyl or aryl groups, mono, di, or trialkoxysilanes having reactive functional groups.
  • alkoxysilanes diamine group-containing alkoxysilanes are preferable from the viewpoint of excellent adsorbability with metals.
  • Examples of the diamine group-containing alkoxysilane include 3- (2-aminoethylamino) propyltrimethoxysilane, 3- (2-aminoethylamino) propylmethyldimethoxysilane, and the like.
  • Examples of commercially available diamine group-containing alkoxysilanes include the following. “KBM-602” and “KBM-603” manufactured by Shin-Etsu Chemical Co., Ltd. “TSL8340” and “TSL8345” manufactured by Momentive Performance Materials Japan.
  • solvents other than tDCE, HFE-347pc-f and organic solvent (B1), or other additives include nitromethane, nitroethane, nitropropane, nitrobenzene, diethylamine, triethylamine, isopropylamine, diisopropylamine, butylamine , Isobutylamine, tert-butylamine, ⁇ -picoline, N-methylbenzylamine, diallylamine, N-methylmorpholine, phenol, o-cresol, m-cresol, p-cresol, thymol, p-tert-butylphenol, tert-butyl Catechol, catechol, isoeugenol, o-methoxyphenol, 4,4'-dihydroxyphenyl-2,2-propane, isoamyl salicylate, benzyl salicylate, methyl salicylate 2,6-di-t-butyl-p-cre
  • the proportion of the lubricant (A) is preferably 0.01 to 50% by mass, more preferably 0.05 to 30% by mass, and further preferably 0.1 to 20% by mass, out of 100% by mass of the lubricant solution. .
  • the ratio of the lubricant (A) is within the above range, it is easy to adjust the thickness of the coating film when the lubricant solution is applied and the thickness of the lubricant coating after drying to an appropriate range.
  • Lubricant (A) may consist of diamine-modified silicone oil alone or may contain other lubricants.
  • the proportion of the diamine-modified silicone oil is preferably 1 to 99% by mass in 100% by mass of the lubricant (A). More preferably, it is -95 mass%, and further preferably 20-90 mass%.
  • the proportion of the other lubricant is preferably 1 to 99% by mass, more preferably 5 to 90% by mass, and still more preferably 10 to 80% by mass, out of 100% by mass of the lubricant (A).
  • the ratio of the solvent (B) is preferably 50 to 99.99% by mass, more preferably 70 to 99.95% by mass, and further preferably 80 to 99.9% by mass, out of 100% by mass of the lubricant solution. If the ratio of the solvent (B) is within the above range, it is easy to adjust the thickness of the coating film when the lubricant solution is applied and the thickness of the lubricant coating after drying to an appropriate range.
  • the proportion of tDCE is 40 to 70% by mass, preferably 45 to 60% by mass, more preferably 50 to 55% by mass, out of the total 100% by mass of tDCE and HFE-347pc-f.
  • the ratio of HFE-347pc-f is 30 to 60% by mass, preferably 40 to 55% by mass, and more preferably 45 to 50% by mass, out of the total 100% by mass of tDCE and HFE-347pc-f.
  • the total ratio of tDCE and HFE-347pc-f is preferably 50 to 100% by mass, more preferably 75 to 100% by mass, and further preferably 80 to 100% by mass, out of 100% by mass of the solvent (B).
  • the solvent (B) contains the organic solvent (B1)
  • the total proportion of tDCE and HFE-347pc-f is preferably 50 to 99.9% by mass, out of 100% by mass of the solvent (B), and 75 to 99.9% by mass is more preferable, and 80 to 99.9% by mass is more preferable.
  • the proportion of the organic solvent (B1) needs to be adjusted as appropriate within the range where the solvent (B) does not have a flash point according to the flammability characteristics of the organic solvent (B1). 0.1 to 50% by mass is preferable, 0.1 to 25% by mass is more preferable, and 0.1 to 20% by mass is further preferable. If the ratio of the total of tDCE and HFE-347pc-f and the ratio of the organic solvent (B1) are within the above ranges, the effects of the present invention are sufficiently exhibited.
  • the proportion of the additive (C) is preferably 5% by mass or less, more preferably 3% by mass or less, and further preferably 1% by mass or less, out of 100% by mass of the lubricant solution. If the ratio of the additive (C) is within the above range, the effects of the present invention are sufficiently exhibited.
  • the proportion of the diamine group-containing alkoxysilane is preferably 0.01 to 5% by mass, and 0.05 to 3% by mass in 100% by mass of the lubricant solution. More preferred is 0.1 to 1% by mass.
  • the ratio of the diamine group-containing alkoxysilane is equal to or higher than the lower limit, the effect as a crosslinking agent is sufficiently exhibited. If the ratio of the diamine group-containing alkoxysilane is not more than the above upper limit, the effects of the present invention are sufficiently exhibited.
  • the lubricant solution of the present invention uses tDCE and HFE-347pc-f, which have a small ozone depletion coefficient and a global warming coefficient, as a solvent, and thus does not adversely affect the global environment. Further, as a solvent, tDCE having excellent solubility of diamine-modified silicone oil and HFE-347pc-f having low solubility but no flash point of diamine-modified silicone oil are used at a specific ratio. The solubility of the modified silicone oil is excellent, the cloudiness or the lubricant does not separate during storage of the lubricant solution, and the lubricant solution does not have a flash point.
  • goods with a lubricant film of this invention has the following process (a) and process (b).
  • the lubricant solution of the present invention is applied to the surface of an object to be coated.
  • the step (b) evaporates the solvent (B) in the lubricant solution applied to the surface of the object to be coated, and forms a lubricant film that is a film containing the lubricant (A) on the surface of the object to be coated.
  • Examples of the object to be coated include various materials such as metal, plastic, elastomer, glass, and ceramic, and metal is preferable.
  • Specific examples of the object to be coated include an injection needle and cylinder of a syringe, a medical tube component, a metal blade, a catheter, and the like, and an injection needle is preferable.
  • Examples of the method of applying the lubricant solution include application by brush, application by spray, application by immersing an object to be coated in the lubricant solution, and the like.
  • Process (b) As a method for evaporating the solvent (B) in the lubricant solution applied to the surface of the object to be coated, a known drying method may be mentioned. Examples of the drying method include air drying and drying by heating. The drying temperature is preferably 20 to 100 ° C. By evaporating the solvent (B) in the lubricant solution applied to the object to be coated, a lubricant coating film is formed on the surface of the object to be coated. Thus, an article with a lubricant coating provided with a lubricant coating on the surface of the object to be coated is manufactured.
  • the method for producing an article with a lubricant coating of the present invention uses the lubricant solution of the present invention containing tDCE and HFE-347pc-f having a low ozone depletion coefficient and a global warming coefficient as a solvent. No adverse effect.
  • the lubricant solution of the present invention is excellent in solubility of the diamine-modified silicone oil and does not separate from the cloudiness or lubricant during storage, a uniform lubricant coating can be formed.
  • the lubricant solution of the present invention having no flash point is used, an article with a lubricant coating can be produced safely.
  • Examples 1 to 5 and 7 to 11 are reference examples
  • Examples 6, 12, 13, 16 to 21, 23 to 27, 30, 31, 34, and 35 are examples.
  • Examples 14, 15, 22, and 28 29, 32 and 33 are comparative examples.
  • Solubility test 100 g of the solvent (B) prepared below was put into a heat-resistant glass bottle, and a predetermined amount of the following silicone oil as a test object was added to the solvent (B) at 23 ° C. The state of the lubricant solution immediately after the test object was added at 23 ° C. and the state of the lubricant solution stored at 23 ° C. for 5 days were observed, and the solubility was evaluated according to the following criteria. A: Excellent, no cloudiness or separation of lubricant is observed. B: Although it is good and thin cloudiness is seen, there is no problem in practical use. C: Poor and clearly cloudy or lubricant separated.
  • Examples 3 and 9 epoxy-modified silicone oil (manufactured by Shin-Etsu Chemical Co., Ltd., KF-101) was used.
  • Examples 4 and 10 monoamine-modified silicone oil (manufactured by Shin-Etsu Chemical Co., Ltd., KF-868) was used.
  • Examples 5 and 11 hydrogen-modified silicone oil (manufactured by Shin-Etsu Chemical Co., Ltd., KF-99) was used.
  • Examples 6, 12, and 13 diamine-modified silicone oil (manufactured by Shin-Etsu Chemical Co., Ltd., KF-859) was used.
  • Example 14 since the ratio of tDCE was large, the solvent had a flash point. In Examples 16 to 21 and 23 to 25, since the ratio of tDCE to HFE-347pc-f is within the range of the present invention, the diamine-modified silicone oil is dissolved and the solvent (B) has no flash point. It was. In Example 22, since the ratio of HFE-347pc-f was large, the diamine-modified silicone oil did not dissolve, and the lubricant solution separated into two layers immediately after the addition of the diamine-modified silicone oil.
  • Novec registered trademark
  • HFE-71DE manufactured by 3M Japan
  • Example 34 [Application test of lubricant solution]
  • a diamine-modified silicone oil (manufactured by Shin-Etsu Chemical Co., Ltd., KF-859) was added to the solvent (B) so that the oil concentration in the solution was 3% by mass to prepare a lubricant solution.
  • a lubricant solution is applied to the surface of an aluminum vapor-deposited plate obtained by vapor-depositing aluminum on an iron plate with an average thickness of about 0.4 mm, and air-dried at a temperature of 19 to 21 ° C.
  • a lubricant coating was formed. No white turbidity was observed in the lubricant solution, and the solvent (B) quickly evaporated from the lubricant solution after application, and the state of the lubricant coating was also good.
  • Example 35 [Application test of lubricant solution] A solvent (B) composed of 50.5% by mass of tDCE, 47.5% by mass of HFE-347pc-f, and 2% by mass of ethanol was prepared. A lubricant solution was prepared in the same manner as in Example 34 except that the solvent (B) was used, and a lubricant coating film was formed on the surface of the aluminum vapor deposition plate. No white turbidity was observed in the lubricant solution, and the solvent (B) quickly evaporated from the lubricant solution after application, and the state of the lubricant coating was also good.
  • the lubricant solution of the present invention is useful as a lubricant solution for forming a lubricant coating on the surface of a metal such as an injection needle.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne une solution de lubrifiant comportant: un lubrifiant (A) contenant une huile de silicone à modification diamine et un solvant (B) contenant du trans -1,2-dichloroéthylène (tDCE) et du 1,1,2,2-tétrafluoro -1- (2,2,2-trifluoroéthoxy) éthane (HFE -347pc -f) ; contenant 40 à 70 % de tDCE en masse totale de 100 % de tDCE et de HFE -347pc-f; et contenant 30 à 60 % de HFE-347pc-f en masse totale de 100 % de tDCE et de HFE-347pc-f.
PCT/JP2016/052278 2015-01-27 2016-01-27 Solution de lubrifiant et procédé pour la fabrication d'article avec film de revêtement lubrifiant WO2016121795A1 (fr)

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JP2016572087A JP6686911B2 (ja) 2015-01-27 2016-01-27 潤滑剤溶液、および潤滑剤塗膜付き物品の製造方法

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020175277A1 (fr) * 2019-02-26 2020-09-03 富士フイルム株式会社 Adhésif pour endoscope, produit durci associé, endoscope et procédé de fabrication associé

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20210005204A (ko) * 2018-05-03 2021-01-13 더 케무어스 컴퍼니 에프씨, 엘엘씨 퍼플루오로헵텐을 포함하는 3성분 및 4성분 공비혼합물 및 공비혼합물-유사 조성물
BR112022004557A2 (pt) 2019-09-13 2022-07-26 Spotless Mat Inc Formulações e processos para gerar superfícies repelentes

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56118497A (en) * 1980-02-26 1981-09-17 Toshiba Silicone Co Ltd Method for imparting slip property to surface of article
JPS56119262A (en) * 1980-02-26 1981-09-18 Toshiba Silicone Injection needle
JPH07178159A (ja) * 1993-12-24 1995-07-18 Toshiba Silicone Co Ltd 注射針
JPH10324652A (ja) * 1997-05-22 1998-12-08 Agency Of Ind Science & Technol 含フッ素エーテルと塩素系有機溶剤からなる共沸及び共沸様組成物
WO2004005445A1 (fr) * 2002-07-03 2004-01-15 Asahi Glass Company, Limited Composition de solvant
JP2005097248A (ja) * 2003-08-25 2005-04-14 Asahi Glass Co Ltd 有機化学物質を希釈するための溶剤、潤滑剤溶液、および潤滑剤の塗布方法
WO2013161723A1 (fr) * 2012-04-23 2013-10-31 旭硝子株式会社 Solution lubrifiante et procédé de production d'un article doté d'un revêtement lubrifiant

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69638056D1 (de) * 1995-05-16 2009-11-26 Minnesota Mining & Mfg Azeotropähnliche zusammensetzungen und ihre verwendung
AU2001279661B2 (en) * 2000-06-23 2006-07-06 International Coatings Limited Ambient temperature curing coating composition
JP2005306902A (ja) * 2004-04-16 2005-11-04 Asahi Glass Co Ltd コーティング用シリコーン溶液、およびシリコーン化合物の塗布方法
WO2012121749A1 (fr) * 2011-03-10 2012-09-13 E. I. Du Pont De Nemours And Company Compositions azéotropiques et analogues à des azéotropes de méthylperfluorohepténéthers et de trans-dichloroéthylène et leurs utilisations

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56118497A (en) * 1980-02-26 1981-09-17 Toshiba Silicone Co Ltd Method for imparting slip property to surface of article
JPS56119262A (en) * 1980-02-26 1981-09-18 Toshiba Silicone Injection needle
JPH07178159A (ja) * 1993-12-24 1995-07-18 Toshiba Silicone Co Ltd 注射針
JPH10324652A (ja) * 1997-05-22 1998-12-08 Agency Of Ind Science & Technol 含フッ素エーテルと塩素系有機溶剤からなる共沸及び共沸様組成物
WO2004005445A1 (fr) * 2002-07-03 2004-01-15 Asahi Glass Company, Limited Composition de solvant
JP2005097248A (ja) * 2003-08-25 2005-04-14 Asahi Glass Co Ltd 有機化学物質を希釈するための溶剤、潤滑剤溶液、および潤滑剤の塗布方法
WO2013161723A1 (fr) * 2012-04-23 2013-10-31 旭硝子株式会社 Solution lubrifiante et procédé de production d'un article doté d'un revêtement lubrifiant

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020175277A1 (fr) * 2019-02-26 2020-09-03 富士フイルム株式会社 Adhésif pour endoscope, produit durci associé, endoscope et procédé de fabrication associé
JPWO2020175277A1 (ja) * 2019-02-26 2021-12-02 富士フイルム株式会社 内視鏡用接着剤及びその硬化物、並びに内視鏡及びその製造方法
JP7100189B2 (ja) 2019-02-26 2022-07-12 富士フイルム株式会社 内視鏡用接着剤及びその硬化物、並びに内視鏡及びその製造方法
JP2022130550A (ja) * 2019-02-26 2022-09-06 富士フイルム株式会社 内視鏡用接着剤及びその硬化物、並びに内視鏡及びその製造方法
JP7257578B2 (ja) 2019-02-26 2023-04-13 富士フイルム株式会社 内視鏡用接着剤及びその硬化物、並びに内視鏡及びその製造方法

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