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WO2018186040A1 - Liquide ionique, lubrifiant pour support d'enregistrement magnétique et support d'enregistrement magnétique - Google Patents

Liquide ionique, lubrifiant pour support d'enregistrement magnétique et support d'enregistrement magnétique Download PDF

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Publication number
WO2018186040A1
WO2018186040A1 PCT/JP2018/006322 JP2018006322W WO2018186040A1 WO 2018186040 A1 WO2018186040 A1 WO 2018186040A1 JP 2018006322 W JP2018006322 W JP 2018006322W WO 2018186040 A1 WO2018186040 A1 WO 2018186040A1
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Prior art keywords
ionic liquid
general formula
lubricant
recording medium
magnetic recording
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PCT/JP2018/006322
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English (en)
Japanese (ja)
Inventor
信郎 多納
弘毅 初田
近藤　洋文
パンカジュ バヘル
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デクセリアルズ株式会社
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Priority claimed from JP2018025838A external-priority patent/JP7033949B2/ja
Application filed by デクセリアルズ株式会社 filed Critical デクセリアルズ株式会社
Publication of WO2018186040A1 publication Critical patent/WO2018186040A1/fr

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    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B5/00—Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
    • G11B5/62—Record carriers characterised by the selection of the material
    • G11B5/72—Protective coatings, e.g. anti-static or antifriction
    • G11B5/725—Protective coatings, e.g. anti-static or antifriction containing a lubricant, e.g. organic compounds
    • G11B5/7253—Fluorocarbon lubricant
    • G11B5/7257—Perfluoropolyether lubricant
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/06—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
    • C10M105/58—Amines, e.g. polyalkylene polyamines, quaternary amines
    • C10M105/60—Amines, e.g. polyalkylene polyamines, quaternary amines having amino groups bound to an acyclic or cycloaliphatic carbon atom
    • C10M105/62—Amines, e.g. polyalkylene polyamines, quaternary amines having amino groups bound to an acyclic or cycloaliphatic carbon atom containing hydroxy groups
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/72—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing sulfur, selenium or tellurium
    • 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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products

Definitions

  • the present invention relates to an ionic liquid, a lubricant for a magnetic recording medium, and a magnetic recording medium.
  • the gap between the head and the disk is becoming smaller year by year, and in recent years, the gap is on the order of several nm to sub-nm. For this reason, contact wear of the disk by the head is likely to occur, leading to a decrease in recording reliability.
  • a carbon protective layer and a lubricant layer are provided on the hard disk (HD) surface to prevent contact wear.
  • a perfluoropolyether (PFPE) having a polar functional group represented by a hydroxyl group represented by the following structural formula is used for the lubricant layer (see, for example, Patent Documents 1 and 2).
  • Such end-functionalized PFPE is known to exhibit high wear resistance, evaporation resistance, and scattering resistance even when the lubricant layer is thinned by adsorbing to the carbon protective layer. It is often used in HD (for example, see Non-Patent Document 1).
  • PFPE is known to exhibit high wear resistance even in a thin film at a monomolecular film level, but naturally it cannot be made thinner than a monomolecular film, and its thickness depends on the molecular weight of the PFPE used. To do. As the recording density is expected to increase further in the future, it is expected that the film thickness will be reduced and the molecular weight will be lowered. However, if the molecular weight is reduced, the heat resistance and scattering resistance are expected to be reduced. Has its limits.
  • a recording system called a HAMR (Heat-Assist Magnetic Recording) system has been developed as a system for further improving the recording capacity and recording speed of a magnetic disk.
  • recording capacity, speed, and reliability can be improved by locally heating a recording portion with near-field light and recording and reproducing a magnetic field while applying a thermal offset.
  • the disk is locally heated to around 200 ° C. (see Non-Patent Document 2). Therefore, the lubricant used in this method is required to have a thermal stability of 200 ° C. or higher (preferably 250 ° C. or higher in consideration of long-term durability).
  • the above-mentioned PFPE has a problem that the thermal stability is insufficient.
  • Lubricant ionic liquid is one method for improving the thermal stability of the lubricant.
  • PFPE having an acid at the terminal is reacted with alkylamine to form an ammonium salt ionic liquid. This technique has been reported to exhibit excellent friction and lubrication properties while maintaining a high pyrolysis temperature.
  • the lubricant for HD is generally used for dip coating after being diluted with a fluorine-based solvent (for example, 2H, 3H-decafluoropentane (manufacturer: DuPont Mitsui (Vertell XF))).
  • a fluorine-based solvent for example, 2H, 3H-decafluoropentane (manufacturer: DuPont Mitsui (Vertell XF)
  • a fluorine-based solvent for example, 2H, 3H-decafluoropentane (manufacturer: DuPont Mitsui (Vertell XF)
  • a fluorine-based solvent for example, 2H, 3H-decafluoropentane (manufacturer: DuPont Mitsui (Vertell XF)
  • Patent Document 3 the above-mentioned ionic liquid has a problem that it cannot be uniformly applied due to poor solubility in these fluorinated solvents. Therefore
  • HD is required to have wear resistance that does not crash even if it is repeatedly worn.
  • improvement of the fluidity of the lubricant is known (see Non-Patent Document 3 and Patent Document 4). It is known that the lubricant layer is thinned by pressure and contact as the head passes over the substrate. If the lubricant layer remains thin, the head tends to be worn when contact between the head and the disk occurs. That is, if the fluidity of the lubricant is poor or the lubricant is solid, the durability of the head is deteriorated. However, when the fluidity is high, the thinned lubricant can be restored by backfilling, and the wear resistance becomes high. For this reason, it is considered important that the recording medium is liquid at room temperature where it is used.
  • the present invention makes it a subject to solve the said various problems in the past and to achieve the following objectives. That is, the present invention provides an ionic liquid having a high bond rate despite excellent heat stability and wear characteristics, and further excellent solubility and fluidity in a fluorinated solvent, and a magnetic material using the ionic liquid. It is an object of the present invention to provide a recording medium lubricant and a magnetic recording medium using the magnetic recording medium lubricant.
  • Means for solving the problems are as follows. That is, ⁇ 1> having a cation component and an anion component;
  • the cation component is an ionic liquid having a group having a perfluoropolyether chain and a group having a hydroxyl group.
  • the ionic liquid according to ⁇ 1> which is represented by the following general formula (1).
  • Rf represents a perfluoropolyether chain having a perfluoroalkyloxy chain having 1 to 4 carbon atoms as a repeating unit.
  • X represents either a single bond or a divalent linking group.
  • R 1 represents an alkyl group having a hydroxyl group.
  • R 2 and R 3 each independently represents an alkyl group having 1 to 4 carbon atoms (provided that R 2 and R 3 are bonded to form a nitrogen-containing hydrocarbon ring having 2 to 8 carbon atoms). You may).
  • Z ⁇ represents the anion component.
  • R 1 represents an alkyl group having a hydroxyl group.
  • R 2 and R 3 each independently represents an alkyl group having 1 to 4 carbon atoms (provided that R 2 and R 3 are bonded to form a nitrogen-containing hydrocarbon ring having 2 to 8 carbon atoms). You may).
  • m represents an integer of 0 to 10.
  • n represents an integer of 2 to 10.
  • p represents an integer of 1 to 20.
  • Z ⁇ represents the anion component.
  • ⁇ 4> The ionic liquid according to any one of ⁇ 1> to ⁇ 3>, wherein the anion component has a fluorinated hydrocarbon group.
  • ⁇ 5> The ⁇ 1> to ⁇ 4>, wherein the anion component is represented by any one of the following general formula (I), the following general formula (II), the following general formula (III), and the following general formula (IV): Or an ionic liquid according to any one of the above.
  • x represents an integer of 0 to 7.
  • x1 and x2 each independently represents an integer of 0 to 8.
  • x3 represents an integer of 1 to 8.
  • n represents an integer of 1 to 8.
  • the above-described problems can be solved, and the bond rate is high despite excellent thermal stability and wear characteristics, and further excellent solubility and fluidity in a fluorinated solvent.
  • An ionic liquid, a magnetic recording medium lubricant using the ionic liquid, and a magnetic recording medium using the magnetic recording medium lubricant can be provided.
  • FIG. 1 is a sectional view showing an example of a hard disk according to an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view showing an example of a magnetic tape according to an embodiment of the present invention.
  • the ionic liquid of the present invention has an anion component and a cation component. That is, the ionic liquid is composed of the anion component and the cation component.
  • the present inventors have conducted intensive studies. went.
  • the cation component has a group having a perfluoropolyether chain and a group having a hydroxyl group, so that it has excellent thermal stability and wear characteristics.
  • an ionic liquid having a high bond rate can be obtained despite excellent solubility in a fluorine-based solvent and fluidity.
  • the ionic liquid can be suitably used for a lubricant for magnetic recording media.
  • the present inventors consider the reason why the bond rate is high in spite of excellent thermal stability and solubility in a fluorine-based solvent and excellent fluidity as follows. Yes.
  • the ionic liquid itself is excellent in thermal stability.
  • the cationic component has a perfluoropolyether chain, it has excellent wear characteristics and fluorine-based solvent solubility and has a low melting point. Due to the low melting point, the fluidity at room temperature (25 ° C.) is excellent.
  • the cation component has a hydroxyl group, the bond rate can be increased without reducing the fluorine-based solvent solubility and fluidity.
  • the cationic component has a group having a perfluoropolyether chain and a group having a hydroxyl group.
  • the cation component is preferably a quaternary ammonium cation.
  • the quaternary ammonium cation is preferably a cation represented by the following general formula (1-1).
  • Rf represents a perfluoropolyether chain having a perfluoroalkyloxy chain having 1 to 4 carbon atoms as a repeating unit.
  • X represents either a single bond or a divalent linking group.
  • R 1 represents an alkyl group having a hydroxyl group.
  • R 2 and R 3 each independently represents an alkyl group having 1 to 4 carbon atoms (provided that R 2 and R 3 are bonded to form a nitrogen-containing hydrocarbon ring having 2 to 8 carbon atoms). You may).
  • the molecular weight of the perfluoropolyether chain or Rf is not particularly limited and may be appropriately selected depending on the intended purpose, but is preferably 1,500 or less, more preferably 1,000 or less, and more preferably 600 or less. preferable. There is no restriction
  • the perfluoropolyether chain or Rf is not particularly limited and may be appropriately selected depending on the intended purpose, but is preferably a group represented by the following general formula (1-1-1).
  • n represents an integer of 2 to 10 and is preferably an integer of 2 to 6.
  • the divalent linking group in X is not particularly limited and may be appropriately selected depending on the intended purpose. However, it preferably has an alkylene group having 2 or more carbon atoms, and an alkylene group having 2 to 10 carbon atoms is preferred. More preferably.
  • the divalent linking group may be a group used for synthesis reasons when introducing an Rf group into the nitrogen atom (N) of the cation represented by the general formula (1-1).
  • R 1 represents an alkyl group having a hydroxyl group.
  • the number of carbon atoms of the alkyl group is not particularly limited and may be appropriately selected depending on the intended purpose, but is preferably 1 to 18, more preferably 1 to 10, still more preferably 1 to 6, and even more preferably 2 to 4 Is particularly preferred.
  • the number of hydroxyl groups in R 1 is not particularly limited and may be appropriately selected depending on the intended purpose, but is preferably 1 to 4, and more preferably 1 to 2.
  • R 2 and R 3 each independently represent an alkyl group having 1 to 4 carbon atoms (provided that R 2 and R 3 are combined to form a nitrogen-containing hydrocarbon ring having 2 to 8 carbon atoms). May be formed).
  • the nitrogen-containing hydrocarbon ring having 2 to 8 carbon atoms include an alkyleneimine ring.
  • the alkyleneimine ring include an aziridine ring, an azetidine ring, a pyrrolidine ring, a piperidine ring, and a hexamethyleneimine ring.
  • the quaternary ammonium cation is more preferably a cation represented by the following general formula (2-1).
  • R 1 represents an alkyl group having a hydroxyl group.
  • R 2 and R 3 each independently represents an alkyl group having 1 to 4 carbon atoms (provided that R 2 and R 3 are bonded to form a nitrogen-containing hydrocarbon ring having 2 to 8 carbon atoms). You may).
  • m represents an integer of 0 to 10.
  • n represents an integer of 2 to 10.
  • p represents an integer of 1 to 20.
  • Z ⁇ represents the anion component.
  • p may be, for example, an integer from 1 to 18, an integer from 1 to 16, or an integer from 1 to 10.
  • p is preferably an integer of 2 to 8, and more preferably an integer of 3 to 6.
  • p is preferably an integer of 7 to 18, more preferably an integer of 8 to 16, and particularly preferably an integer of 9 to 15.
  • the anion component is not particularly limited and may be appropriately selected depending on the intended purpose. However, from the viewpoint of solubility, it preferably has a fluorinated hydrocarbon group, and the following general formula (I) and the following general formula More preferably, it is represented by any one of (II), the following general formula (III), and the following general formula (IV).
  • the fluorinated hydrocarbon group may be a fully fluorinated hydrocarbon group or a partially fluorinated hydrocarbon group.
  • x represents an integer of 0 to 7, preferably an integer of 0 to 3.
  • x1 and x2 each independently represents an integer of 0 to 8, preferably an integer of 1 to 8, and more preferably an integer of 1 to 4.
  • x3 represents an integer of 1 to 8, and an integer of 1 to 3 is preferable.
  • n represents an integer of 1 to 8, and an integer of 1 to 4 is preferable.
  • the ionic liquid is preferably represented by the following general formula (1).
  • Rf represents a perfluoropolyether chain having a perfluoroalkyloxy chain having 1 to 4 carbon atoms as a repeating unit.
  • X represents either a single bond or a divalent linking group.
  • R 1 represents an alkyl group having a hydroxyl group.
  • R 2 and R 3 each independently represents an alkyl group having 1 to 4 carbon atoms (provided that R 2 and R 3 are bonded to form a nitrogen-containing hydrocarbon ring having 2 to 8 carbon atoms). You may).
  • Z ⁇ represents the anion component.
  • Rf in the general formula (1), X, exemplary of R 1, R 2, and exemplary R 3 are, Rf in the general formula (1-1) in, X, R 1, R 2, and R 3
  • the preferred embodiments are also the same.
  • the ionic liquid is more preferably represented by the following general formula (2).
  • R 1 represents an alkyl group having a hydroxyl group.
  • R 2 and R 3 each independently represents an alkyl group having 1 to 4 carbon atoms (provided that R 2 and R 3 are bonded to form a nitrogen-containing hydrocarbon ring having 2 to 8 carbon atoms). You may).
  • m represents an integer of 0 to 10.
  • n represents an integer of 2 to 10.
  • p represents an integer of 1 to 20.
  • Z ⁇ represents the anion component.
  • Exemplary R 1, R 2, and R 3 in the general formula (2) is, R 1, R 2 in the formula (1), and are the same as exemplified for R 3, a preferred embodiment also the same is there.
  • Examples of m, n, and p in the general formula (2) are the same as those of m, n, and p in the general formula (2-1), and preferred embodiments are also the same.
  • the ionic liquid of the present invention is a liquid at normal temperature (25 ° C.).
  • the melting point of the ionic liquid is preferably 25 ° C. or less, and more preferably 10 ° C. or less.
  • the lower limit of the melting point of the ionic liquid is not particularly limited and may be appropriately selected depending on the intended purpose. However, the melting point of the ionic liquid is preferably ⁇ 100 ° C. or higher.
  • the melting point can be determined, for example, by differential scanning calorimetry. When the ionic liquid has a melting point of room temperature or lower, it becomes an ionic liquid having fluidity at room temperature.
  • the lubricant for a magnetic recording medium of the present invention contains an ionic liquid, and further contains other components as necessary.
  • the ionic liquid is the ionic liquid of the present invention.
  • the ionic liquid may be used alone or in combination with a conventionally known lubricant.
  • Known lubricants include, for example, long chain carboxylic acids, long chain carboxylic acid esters, perfluoroalkyl carboxylic acid esters, carboxylic acid perfluoroalkyl esters, perfluoroalkyl carboxylic acid perfluoroalkyl esters, perfluoropolyether derivatives, and the like. Is mentioned.
  • the magnetic recording medium lubricant may be used in combination with an extreme pressure agent at a blending ratio of about 30:70 to 70:30.
  • the extreme pressure agent acts to prevent friction and wear by forming a reaction product film by reacting with the metal surface due to frictional heat generated when metal contact occurs partially in the boundary lubrication region.
  • the extreme pressure agent for example, any of a phosphorus extreme pressure agent, a sulfur extreme pressure agent, a halogen extreme pressure agent, an organometallic extreme pressure agent, a composite extreme pressure agent, and the like can be used.
  • the rust inhibitor may be any rust inhibitor that can be used as a rust inhibitor for this type of magnetic recording medium.
  • the rust preventive agent may be used as a lubricant, but a magnetic layer is formed on a nonmagnetic support, a rust preventive layer is applied thereon, and then a lubricant layer is applied. Thus, it may be applied in two or more layers.
  • solvent examples include organic solvents.
  • examples of the organic solvent include a fluorine-based solvent and an alcohol-based solvent.
  • examples of the alcohol solvent include isopropyl alcohol (IPA) and ethanol.
  • examples of the fluorine-based solvent include hydrofluoroethers [for example, C 3 F 7 OCH 3 , C 4 F 9 OCH 3 , C 4 F 9 OC 2 H 5 , C 2 F 5 CF (OCH 3 ) C 3 F 7 , C 5 H 2 F 10 ] and the like.
  • the fluorinated solvent may be a commercially available product.
  • Examples of the commercially available products include Novec TM 7000, 7100, 7200, 7300, 71IPA manufactured by 3M, Vertrel XF, X-P10 manufactured by Mitsui DuPont Fluorochemical Co., Ltd., and the like. These solvents may be used alone or in combination of two or more.
  • the magnetic recording medium of the present invention includes a nonmagnetic support, a magnetic layer, and the magnetic recording medium lubricant of the present invention, and further includes other members as necessary.
  • the magnetic layer is formed on the nonmagnetic support. That is, the magnetic layer is disposed on the nonmagnetic support.
  • the magnetic recording medium lubricant is formed on the magnetic layer. That is, the magnetic recording medium lubricant is disposed on the magnetic layer.
  • the lubricant can be applied to a so-called metal thin film type magnetic recording medium in which a magnetic layer is formed on the surface of a nonmagnetic support by a technique such as vapor deposition or sputtering.
  • the present invention can also be applied to a magnetic recording medium having a configuration in which an underlayer is interposed between a nonmagnetic support and a magnetic layer. Examples of such a magnetic recording medium include a magnetic disk and a magnetic tape.
  • FIG. 1 is a cross-sectional view showing an example of a hard disk.
  • This hard disk has a structure in which a substrate 11, an underlayer 12, a magnetic layer 13, a carbon protective layer 14, and a lubricant layer 15 are sequentially laminated.
  • FIG. 2 is a cross-sectional view showing an example of a magnetic tape.
  • This magnetic tape has a structure in which a backcoat layer 25, a substrate 21, a magnetic layer 22, a carbon protective layer 23, and a lubricant layer 24 are sequentially laminated.
  • the nonmagnetic support corresponds to the substrate 11 and the underlayer 12, and in the magnetic tape shown in FIG. 2, the nonmagnetic support corresponds to the substrate 21.
  • a rigid substrate such as an Al alloy plate or a glass plate
  • an oxide film such as an alumite treatment or Ni-P film may be formed on the substrate surface to harden the surface. Good.
  • the magnetic layers 13 and 22 are formed as a continuous film by a technique such as plating, sputtering, vacuum deposition, or plasma CVD.
  • the magnetic layers 13 and 22 include metals such as Fe, Co, Ni, Co—Ni alloys, Co—Pt alloys, Co—Ni—Pt alloys, Fe—Co alloys, Fe—Ni alloys, In-plane magnetization recording metal magnetic film made of Fe—Co—Ni alloy, Fe—Ni—B alloy, Fe—Co—B alloy, Fe—Co—Ni—B alloy, etc., Co—Cr alloy Examples thereof include perpendicular magnetic recording metal magnetic thin films such as thin films and Co—O thin films.
  • a nonmagnetic material such as Bi, Sb, Pb, Sn, Ga, In, Ge, Si, or Tl is previously formed on the nonmagnetic support as the underlayer 12.
  • metal magnetic materials are vapor-deposited or sputtered from the vertical direction, and these non-magnetic materials are diffused in the magnetic metal thin film to eliminate orientation and ensure in-plane isotropy and improve coercive force. You may do it.
  • a hard protective layer such as a carbon film, diamond-like carbon film, chromium oxide film, or SiO 2 film may be formed on the surface of the magnetic layers 13 and 22.
  • the coating amount of the magnetic recording medium lubricant is preferably 0.1 mg / m 2 to 100 mg / m 2 , more preferably 0.5 mg / m 2 to 30 mg / m 2 , and Particularly preferred is 5 mg / m 2 to 20 mg / m 2 .
  • a back coat layer 25 may be formed as necessary.
  • the back coat layer 25 is formed by adding a carbon-based fine powder for imparting conductivity to the resin binder and an inorganic pigment for controlling the surface roughness.
  • the lubricant can be applied to a so-called coating type magnetic recording medium in which a magnetic coating film is formed as a magnetic layer by applying a magnetic paint to the surface of a nonmagnetic support. is there.
  • a coating type magnetic recording medium any conventionally known magnetic powder, resin binder and the like constituting the nonmagnetic support, the magnetic coating film, and the like can be used.
  • the nonmagnetic support for example, a polymer support formed of a polymer material typified by polyesters, polyolefins, cellulose derivatives, vinyl resins, polyimides, polyamides, polycarbonates and the like. Examples thereof include a metal substrate made of aluminum alloy, titanium alloy, etc., a ceramic substrate made of alumina glass, etc., a glass substrate, and the like.
  • the shape is not limited at all, and any shape such as a tape shape, a sheet shape, or a drum shape may be used.
  • the non-magnetic support may be subjected to a surface treatment so as to form fine irregularities in order to control the surface property.
  • the magnetic powder examples include ferromagnetic iron oxide particles such as ⁇ -Fe 2 O 3 and cobalt-coated ⁇ -Fe 2 O 3 , ferromagnetic chromium dioxide particles, metals such as Fe, Co, Ni, and the like. Examples thereof include ferromagnetic metal particles made of an alloy containing hexagonal plate-like ferrite fine particles.
  • the resin binder examples include vinyl chloride, vinyl acetate, vinyl alcohol, vinylidene chloride, acrylic acid ester, methacrylic acid ester, styrene, butadiene, acrylonitrile, or a combination of these two or more, polyurethane Resins, polyester resins, epoxy resins and the like are exemplified.
  • a hydrophilic polar group such as a carboxylic acid group, a carboxyl group or a phosphoric acid group may be introduced in order to improve the dispersibility of the magnetic powder.
  • a dispersant In addition to the magnetic powder and the resin binder, a dispersant, an abrasive, an antistatic agent, an antirust agent, and the like may be added to the magnetic coating film as an additive.
  • a method for retaining the lubricant for the magnetic recording medium in such a coating-type magnetic recording medium a method of internally adding the magnetic coating film forming the magnetic coating film formed on the nonmagnetic support. And a method of top-coating the surface of the magnetic layer, or a combination of both. Further, when the magnetic recording medium lubricant is internally added to the magnetic coating film, it is added in the range of 0.2 to 20 parts by mass with respect to 100 parts by mass of the resin binder.
  • the coating amount is preferably 0.1 mg / m 2 to 100 mg / m 2 , and 0.5 mg / m 2. More preferably it is ⁇ 20 mg / m 2 .
  • the ionic liquid is dissolved in a solvent, and the obtained solution is applied or sprayed, or the magnetic recording medium is placed in this solution. What is necessary is just to immerse.
  • the solvent is preferably a fluorinated solvent.
  • fluorinated solvent examples include: Hydrofluoroether [e.g., C 3 F 7 OCH 3, C 4 F 9 OCH 3, C 4 F 9 OC 2 H 5, C 2 F 5 CF (OCH 3) C 3 F 7, C 5 H 2 F 10 ] Etc.
  • the fluorinated solvent may be a commercially available product. Examples of the commercially available products include Novec TM 7000, 7100, 7200, 7300, 71IPA manufactured by 3M, Vertrel XF, X-P10 manufactured by Mitsui DuPont Fluorochemical Co., Ltd., and the like.
  • the magnetic recording medium lubricant according to the present invention By using the magnetic recording medium lubricant according to the present invention, even when a thin lubricant layer is formed, a good lubricating action can be exerted to reduce the friction coefficient, and the thermal stability is high. Sex can be obtained. Further, this lubricating action is not impaired even under severe conditions such as high temperature, low temperature, high humidity, and low humidity.
  • the magnetic recording medium to which the magnetic recording medium lubricant is applied even when a thin lubricant layer is formed, exhibits excellent running performance, wear resistance, durability, etc. due to the lubricating action. Furthermore, thermal stability can be improved.
  • Example 1 ⁇ Synthesis of ionic liquid (1-D)> An ionic liquid (1-D) having a fluorinated triethylene glycol (PFTEG) structure and a hydroxypropyl group in the cation portion and the anion portion being bis (nonafluorobutylsulfonyl) imide was synthesized by the following method.
  • PFTEG fluorinated triethylene glycol
  • Step 1-B In a flask equipped with a stirrer, a thermometer, and a condenser tube, 0.87 g (8.4 mmol) of 3- (dimethylamino) -1-propanol (manufacturer: Tokyo Kasei Kogyo) and ⁇ Step 1-B >> Then, 7.00 g (10.5 mmol) of 3-bromopropyl PFTEG (1-B) synthesized in Step 1 was added, 8 g of acetonitrile was added as a solvent, and the mixture was heated to reflux for 6 hours. The obtained mixture solution was evaporated with an evaporator, decanted with hexane and diethyl ether, and then concentrated again with an evaporator.
  • ELSD LC-MS
  • 6-bromo-1-hexanol maker: Tokyo Chemical Industry
  • p-toluenesulfonyl chloride maker: Tokyo Chemical Industry
  • 79.46 g (417 mmol)
  • Toluene maker: Wako Pure Chemical Industries
  • triethylamine maker: Kanto Chemical 42.2 g (417 mmol) as a base were added and stirred at room temperature for 25 hours. After stirring, the reaction solution was filtered and diethyl ether was added.
  • Step 1-B of Example 1, 100 mmol of fluorinated triethylene glycol monobutyl ether (PFTEG-OH) was replaced with 100 mmol of fluorinated triethylene glycol monomethyl ether (manufacturer: Apollo Scientific), and 3-bromo The same procedure was followed except that 211 mmol of propyl tosylate was replaced with 6-bromohexyl tosylate (3-A) to obtain 3-bromohexyl PFTEG (3-B) in a yield of 40%.
  • PFTEG-OH fluorinated triethylene glycol monobutyl ether
  • Example 1 ⁇ Step 1-D >> The same procedure as in Example 1 ⁇ Step 1-D >> was performed except that 5.0 mmol of bromide salt (1-C) was changed to 5.0 mmol of bromide salt (3-C).
  • An ionic liquid (3-D) was obtained with a yield of 86%.
  • Example 4 ⁇ Synthesis of ionic liquid (4-D)> An ionic liquid (4-D) having a fluorinated triethylene glycol (PFTEG) structure, a hydroxyethyl group, and a pyrrolidine ring in the cation portion, and the anion portion comprising bis (nonafluorobutylsulfonyl) imide is obtained by the following method. Synthesized.
  • PFTEG fluorinated triethylene glycol
  • Example 1 ⁇ Step 1-D >> The same procedure as in Example 1 ⁇ Step 1-D >> was performed except that 5.0 mmol of bromide salt (1-C) was changed to 5.0 mmol of ionic liquid (4-C).
  • the ionic liquid (4-D) was obtained with a yield of 86%.
  • Example 1 The same procedure as in Example 1 was performed except that 6.2 mmol of EF-N445 was replaced with 6.2 mmol of nonafluorobutanesulfonic acid potassium salt (Tokyo Chemical Industry) in ⁇ Step 1-D >> of Example 1.
  • the product was obtained in 98% yield.
  • Example ⁇ Step 1-C >>, except that 8.4 mmol of 3- (dimethylamino) -1-propanol was changed to 8.4 mmol of triethylamine (manufacturer: Tokyo Kasei Kogyo), Example 1 The same operation was performed to obtain a bromide salt (6-C) with a yield of 53%.
  • Example 1 ⁇ Step 1-D >> The same procedure as in Example 1 ⁇ Step 1-D >> was performed except that 5.0 mmol of bromide salt (1-C) was changed to 5.0 mmol of bromide salt (6-C).
  • An ionic liquid (6-D) was obtained with a yield of 60%.
  • Step 1-C In ⁇ Step 1-C >> of Example 1, 10.5 mmol of 3-bromopropyl PFTEG (1-B) was changed to 10.5 mmol of 1-bromooctadecane (manufacturer: Tokyo Kasei Kogyo) to carry out the reaction. . After completion of the reaction, reprecipitation purification was performed in hexane to obtain a bromide salt (7-C) in a yield of 92%.
  • Example 1 ⁇ Step 1-D >> The same operation as in Example 1 ⁇ Step 1-D >> was performed except that 5.0 mmol of bromide salt (1-C) was changed to 5.0 mmol of bromide salt (7-C).
  • the ionic liquid (7-D) was obtained with a yield of 81%.
  • ionic liquid (8-D) having a fluorinated triethylene glycol (PFTEG) structure, a hydroxyethyl group, and a pyrrolidine ring in the cation part, and the anion part comprising bis (nonafluorobutylsulfonyl) imide is obtained by the following method. Synthesized.
  • Step 9-B Synthesis of 12-bromododecyl M-PFTEG (9-B)
  • Step 9-D Synthesis of ionic liquid (9-D)
  • Novec7100 is a hydrofluoroether represented by C 4 F 9 OCH 3 (boiling point 61 ° C.).
  • Comparative Example 3 which is a nonionic liquid
  • the ionic liquids of Examples 1 to 7 and Comparative Examples 1 and 2 showed high heat resistance of 5% weight loss temperature of 300 ° C. or more.
  • the lubricant solution used for dip coating was prepared using the solvents shown in Table 3.
  • the lubricant solution was filtered using a syringe filter (0.2 ⁇ m). Further, the concentration of the ionic liquid in the lubricant solution was set to 0.2% by mass (the ionic liquid of Comparative Example 2 was dissolved in the addition of 0.2% by mass with respect to Vertrel XF).
  • the dip coating was performed by pulling up the magnetic disk from a glass container containing a lubricant solution at a speed of 50 mm / min.
  • the dependence of the dip concentration on the film thickness was investigated by systematically changing the dip concentration conditions for each lubricant.
  • the film thickness was measured by ellipsometry (model number: M-2000, manufacturer: JA Woollam).
  • the average thickness of the formed lubricant layer was adjusted to 10 mm by adjusting the dip concentration for each lubricant.
  • the lubricants of Examples 1 to 7 and Comparative Examples 2 and 3 maintained a coefficient of friction of 0.20 or less even after 100 times of sliding.
  • the initial friction was about the same as that of the example, but the coefficient of repeated friction after 100 times was 0.30 and did not show lubricity.
  • ⁇ bond rate 100 ⁇ (lubricant film thickness after rinsing with a fluorine-based solvent) / (lubricant film thickness before rinsing) [%]
  • the surface of the lubricant-coated hard disk was rinsed with a fluorine-based solvent, and the film thickness of the lubricant before and after rinsing was measured.
  • the lubricant-coated hard disk was produced in the same manner as the method produced in the evaluation of wear characteristics, except that the concentration of the ionic liquid in the lubricant solution was 1.0% by mass.
  • the lubricant film thickness was 10 mm.
  • Vertrel XF was used as the fluorinated solvent. Rinsing was performed by immersing the disc in Vertrel XF for 3 minutes. The film thickness was measured by ellipsometry (model number: M-2000, manufacturer: JA Woollam).
  • UV irradiation was performed before rinsing. It is considered that photoelectrons are generated on the surface of the hard disk during UV irradiation and react with polar functional groups in the lubricant molecular structure.
  • the UV irradiation was performed for 60 seconds at wavelengths of 185 nm and 253 nm and an intensity of 2 mW (254 nm). The results are shown in Table 4.
  • Comparative Example 1 had a relatively low bond rate of less than 25% even after UV 60 irradiation. Note that Comparative Example 2 was not measured because it was not dissolved in Vertrel XF.
  • Examples 1 to 7 showed good characteristics as ionic liquids having all of excellent thermal stability, excellent wear characteristics, excellent fluorine-based solvent solubility, excellent fluidity, and excellent bond ratio. In particular, Examples 6 and 7 had a very good bond rate.
  • the lubricant for magnetic recording medium of the present invention is excellent in thermal stability, wear characteristics and solubility in a fluorine-based solvent, and is also a liquid at room temperature and an excellent bond rate, so that a high recording density magnetic recording medium Can be suitably used.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Magnetic Record Carriers (AREA)

Abstract

L'invention concerne un liquide ionique, caractérisé en ce qu'il contient un composant cationique et un composant anionique, le composant cationique comprenant un groupe ayant une chaîne perfluoropolyéther et un groupe ayant un groupe hydroxyle.
PCT/JP2018/006322 2017-04-04 2018-02-21 Liquide ionique, lubrifiant pour support d'enregistrement magnétique et support d'enregistrement magnétique WO2018186040A1 (fr)

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JP2021014417A (ja) * 2019-07-11 2021-02-12 デクセリアルズ株式会社 イオン液体、潤滑剤、及び磁気記録媒体

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021014417A (ja) * 2019-07-11 2021-02-12 デクセリアルズ株式会社 イオン液体、潤滑剤、及び磁気記録媒体

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