JP2001011032A - Fluorine-containing alkylamine and its production - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the novel subject compound having excellent lubrication characteristics and useful as a lubricant for various machines, apparatus or parts by bringing the compound to have an amino group, a fluorine-containing terminal group and an aliphatic hydrocarbon terminal group. SOLUTION: This fluorine-containing alkylamine is a compound expressed by formula I (R1 is an aliphatic alkyl or an aliphatic alkenyl; R2 is a fluoroalkyl; m is 1-6; n is 1-30; a is l-12), e.g. the compound expressed by formula II. The compound of formula I is obtained by reacting (A) a fluorine-containing alkylamide ester with (B) the solution of a borane tetrahydrofuran complex (catalyst) in tetrahydrofuran at preferably 0-30 deg.C and bringing the reaction product to an amine by reducing a carbonyl group. In the aforesaid reaction the molar ratio of the ingredient A to the catalyst is preferably 1:1-1:5. The aforesaid compound is useful as a material for constituting a lubricant composition. The lubricant composition is preferably brought to contain 40 wt.% of the compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a compound for a lubricant, a method for producing the compound, a lubricant containing the compound, a magnetic recording medium using the lubricant, and a method for producing the magnetic recording medium. For more specifically, a compound for a lubricant used for precision machinery or precision parts or the like where high precision lubrication is required, a method for producing the compound,
The present invention relates to a lubricant containing the compound, a magnetic recording medium using the lubricant, and a method for manufacturing the magnetic recording medium.

[0002]

2. Description of the Related Art With the miniaturization and high precision of mechanical devices and parts, the lubrication mode of sliding parts thereof has also shifted from fluid lubrication to boundary lubrication. In particular, in electronic devices and electronic components such as VTRs and magnetic disks, the use of a ferromagnetic metal thin film for the purpose of improving recording density has resulted in
For sliding between magnetic tape or magnetic disk and magnetic head,
High precision lubrication has become necessary. For example, in a vapor-deposited tape or a hard disk, the lubricant layer on the surface of the magnetic layer is required to minimize the spacing loss between the magnetic recording medium and the magnetic head while increasing the output while securing the durability and reliability. It is formed to have a thickness of only several tens of degrees.
Therefore, development of an organic compound having excellent lubricity as a material for forming the lubricant layer is an important issue. As a lubricant for a metal thin-film type magnetic recording medium, a long-chain carboxylic acid fluoroalkyl ester represented by the following formula (34) (Japanese Patent Laid-Open No. 62-46431) or the following formula (3)
There is a fluoroalkyl monocarboxylic acid ester represented by 5) (JP-A-61-107529). _{C 18 H 35 OCOC 9 F 17} ... (34)

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[0003]

However, the above equation (34)
The lubricant of a long-chain fluoroalkyl carboxylate represented by the formula (1) has a reduced lubricity under a high temperature environment, while the lubricant of a fluoroalkyl monocarboxylic acid ester represented by the above formula (35) has a low humidity. Under such circumstances, there is a problem that lubricity is reduced.

[0004] In view of the above problems, the present invention includes a compound for a lubricant, a method for producing the compound, and a method for producing the compound, which make it possible to obtain a magnetic recording medium with high practical reliability without impairing the electromagnetic conversion characteristics. And a magnetic recording medium using the lubricant, and a method for manufacturing the magnetic recording medium.

[0005]

A first gist of the present invention is as follows.
Exists in fluorine-containing compounds having a specific structure. Such a compound is a fluorine-containing alkylamine represented by the following formula (36).

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As is apparent from the above formula (36), the fluorinated alkylamine of the present invention has a fluoroalkyl terminal group having one fluoroalkylene oxide chain and one aliphatic hydrocarbon terminal in one molecule. The structure has a group (ie, an alkyl terminal group or an alkenyl terminal group) and an amino group. That is, this compound can be said to be a fluorine-containing alkylamine having one amino group. With this structure, when the fluorine-containing compound of the present invention is contained in a lubricant, particularly a lubricant for a magnetic recording medium, the lubricant exhibits excellent lubricating properties. Therefore, the present invention also provides the above-mentioned fluorinated alkylamine of the present invention as a compound for a lubricant.

A second aspect of the present invention resides in a lubricant comprising at least one kind of the above-mentioned fluorine-containing alkylamine of the present invention. The lubricant of the present invention is particularly suitable for forming a lubricant layer of a magnetic recording medium.

[0008] The lubricant of the present invention may further contain at least one fluoropolyether compound. Fluoropolyether compounds also act as lubricants, and by using them together with the fluorinated alkylamine of the present invention, more excellent lubrication performance can be imparted to the lubricant.

[0009] The lubricant of the present invention may further contain at least one organic phosphorus compound. That is, the lubricant of the present invention is a two-component system containing the fluorine-containing alkylamine of the present invention and an organic phosphorus compound, or
A three-component lubricant composition containing the fluorinated alkylamine of the present invention, the above-mentioned fluoropolyether compound and an organic phosphorus compound may be used. The organic phosphorus compound acts as a rust inhibitor and / or an extreme pressure agent. For example, when the lubricant composition is contained in a lubricant layer of a magnetic recording medium, the lubricant layer and the protective film are used. It also plays a role in improving the adhesion strength between the magnetic recording medium and the magnetic recording medium, so that the lubrication performance and durability of the magnetic recording medium can be further improved.

In the present invention, it is preferable to use, as the organic phosphorus compound, a compound selected from the group consisting of organic phosphorus compounds represented by the following general formulas (37) to (45). _{HP (O) (OC n H} 2n + 1) 2 ... (37) P (OC n H 2n + 1) 3 ... (38) P (SC n H 2n + 1) 3 ... (39) O = P (OC _n H _{2n + 1} ) ₃ ... (40) S = P (OC _n H _{2n + 1} ) ₃ ... (41) O = P (SC _n H _{2n + 1} ) ₃ ... (42) S = P (SC _n H) _{2n +} 1) ₃ also _{... (43) (C n H} 2n + 1 O) 2 P (O) OH ... (44) (C n H 2n + 1 O) P (O) (OH) 2 ... (45) The carbon number n of the organic phosphorus compound is preferably 8 to 20.

A third gist of the present invention is a magnetic recording system comprising a ferromagnetic metal film provided on a nonmagnetic support, and a lubricant layer provided on the ferromagnetic metal film via a protective film. A medium, wherein the lubricant layer is present in a magnetic recording medium containing the lubricant composition.

The action and effect of the fluorinated alkylamine of the present invention represented by the general formula (36) in the magnetic recording medium of the present invention are considered to be as follows. It does not limit the invention in any way. The active group containing fluorine in the molecule of the above formula (36) is exposed on the surface of the metal thin film, the surface of the protective film, or the surface of the magnetic head, contributing to lowering the energy of the surface and forming a non-adhesive surface. I do. In addition, the ether bond has the effect of imparting good lubricity by giving flexibility to the rigid fluorine-containing terminal,
This enables the lubricant layer of the magnetic recording medium to have both non-adhesiveness and lubricity. This effect is, when the group containing fluorine is a fluoroether group or a fluoropolyether group having a fluoroalkylene oxide group,
It becomes more noticeable.

Further, the alkyl group or alkenyl group in the molecule of the above formula (36) has a flexible carbon-carbon bond, thereby improving the lubricity of the magnetic recording medium.
Further, due to the presence of the amino group in the molecule, the lubricant layer containing the fluorine-containing alkylamine of the present invention strongly adheres to the surface of the protective film, the surface of the magnetic head, and the surface of the traveling metal member. And, due to the synergistic effect of these respective parts constituting the molecule, the magnetic recording medium of the present invention containing the fluorine-containing alkylamine of the present invention in the lubricant layer can be used in a wide range of environments from a low temperature and low humidity environment to a high temperature and high humidity environment. The lubricity does not decrease underneath.

A fourth aspect of the present invention is to provide a method of manufacturing the magnetic recording medium of the present invention. The method of manufacturing a magnetic recording medium according to the present invention is characterized in the step of forming a lubricant layer, and the other steps can use the steps used in conventional magnetic recording media.

In the step of forming the lubricant layer, the coating liquid prepared by dissolving the compound constituting the lubricant layer, that is, the lubricant composition, in a mixed organic solvent of a hydrocarbon solvent and an alcohol solvent is coated with a protective film. The method is characterized by including a step of coating on top. By using a mixed solvent in which a hydrocarbon-based solvent and an alcohol-based solvent are combined, a uniform thin lubricant layer with extremely little coating unevenness can be formed.
Therefore, according to the manufacturing method of the present invention, it is possible to obtain a highly reliable magnetic recording medium having excellent lubrication performance.

In the method for producing a magnetic recording medium of the present invention, the mixing ratio of the hydrocarbon solvent and the alcohol solvent is preferably in the range of 1: 9 to 9: 1 by weight. Mixing both in this range makes it possible to minimize coating unevenness and is advantageous in terms of cost.

[0017]

BEST MODE FOR CARRYING OUT THE INVENTION The fluorine-containing alkylamine of the present invention has a general formula represented by the following formula (46).

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In the above formula (46), R ₁ is an alkyl group or an alkenyl group, the carbon number of which is 6 to 3;
0, preferably 10 to 24 is suitable. When the number of carbon atoms is less than 6, or when the number of carbon atoms exceeds 30, the lubricity may be reduced.

R ₂ is a fluoroalkyl group, preferably a perfluoroalkyl group, having 1 to 3 carbon atoms.
0, preferably 1 to 8, is suitable. m is usually 1 to 6
And n is usually an integer of 1 to 30, and more preferably an integer of 1 to 8. If m and n are outside these ranges, the lubricity of the magnetic recording medium may decrease.

When the lubricant is contained in the lubricant layer of the magnetic recording medium, for example, when the lubricant is contained in the lubricant layer of the magnetic recording medium, the presence of the fluorine-containing alkylamine having a fluoroether group or a fluoropolyether group is included. The adhesion strength to the film is further improved, and more excellent lubrication properties are imparted to the magnetic recording medium. By the synergistic effect of these, a magnetic recording medium having high durability and improved durability without impairing the electromagnetic conversion characteristics can be obtained.

In the above formula (46), a is an integer of 0 or more, preferably 1 to 12, more preferably 1 to 8.

The fluorinated alkylamine used in the present invention is obtained by reacting a fluorinated alkylamide ester represented by the following general formula (47) with a solution of borane tetrahydrofuran complex (borane THF complex) in tetrahydrofuran (THF), It can be produced by a method in which a carbonyl group is reduced to an amine.

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Further, the fluorine-containing alkylamide ester, which is a raw material of the fluorine-containing alkylamine of the present invention, shows high reactivity with the borane THF complex, so that a single compound can be obtained with high purity and high yield. ,
The inventor of the present application has discovered. This discovery has made it possible to produce the fluorinated alkylamine of the present invention at low cost and on an industrial scale by using the above-described method for producing a fluorinated alkylamine of the present invention.

The fluorinated compound of the present invention is produced by mixing and stirring a fluorinated alkylamide ester and a THF solution of a borane THF complex. The stirring is preferably performed at a temperature in the range of 0 to 30 ° C. More preferably, it is 10 to 20 ° C. If the stirring temperature is lower than this range, unreacted substances tend to remain,
On the other hand, if the temperature rises, it is dangerous because it generates heat.

Solvents that can be used include THF, hydrocarbons (hexane, heptane, octane) and ethers. Catalysts that can be used include borane THF complex, lithium aluminum hydride and the like. The molar ratio between the fluorinated alkylamide ester and the catalyst is
1: 1-1: 5 is preferred.

In order to isolate the target compound from the obtained mixture, the solvent is first removed by distillation under reduced pressure, and the residue is extracted with an organic solvent to obtain a fluorinated alkylamine. This compound was analyzed by infrared spectroscopy (IR), gel permeation chromatography (GPC) and organic mass spectroscopy (F
D-MS).

The thus obtained fluorine-containing alkylamine of the present invention is useful as a material constituting a lubricant. The lubricant composition of the present invention comprising at least one fluorine-containing alkylamine of the present invention is suitable for forming, for example, a lubricant layer of a magnetic recording medium.

The lubricant of the present invention may be a composition containing only one kind of the fluorinated alkylamine of the present invention, or a composition containing two or more kinds. The lubricant of the present invention may be composed of only the fluorinated alkylamine of the present invention, but may be a composition containing other lubricants, rust preventives, extreme pressure agents and the like as appropriate. You may. In that case, the proportion occupied by the fluorinated alkylamine of the present invention is preferably at least 40% by weight, more preferably at least 60% by weight, based on the total amount of the composition. When the proportion of the fluorinated alkylamine of the present invention is less than 40% by weight, for example, when a lubricant layer of a magnetic recording medium is formed with this composition, good lubricating properties cannot be imparted to the magnetic recording medium. There is.

When a commercially available perfluoropolyether-based lubricant is used as the other lubricant, the lubricating performance is further improved. For example, when a lubricant layer of a magnetic recording medium is formed with a lubricant containing the same. In addition, the durability of the magnetic recording medium is improved. As commercially available perfluoropolyethers,
Product name "Fomblin Z" manufactured by Ausimont
Type and “Fomblin Y” type, Du-P
There is a “Krytox” type product name manufactured by Ont Corporation and a “Demnum” type product name manufactured by Daikin Industries, Ltd.

These commercially available perfluoropolyether compounds include a nonpolar type and a type having a polar group. The present invention relates to a polar group selected from a hydroxyl group, a carboxyl group, an ester and a piperonyl group. Is preferred. As a perfluoropolyether having a polar group, a product name “F” manufactured by Ausimmont
"Omblin Z Dol" (having a hydroxyl group as a polar group), "Fomblin Z Diac" (having a carboxyl group as a polar group), "Fomblin A
M2001 "(having a piperonyl group as a polar group), and a product name" Demnum "manufactured by Daikin Industries, Ltd.
SA ”(having a hydroxyl group as a polar group) and“ De ”
mnum SH "(having a carboxyl group as a polar group). The molecular weight of a commercially available perfluoropolyether compound is generally from about 1,000 to about 20,000.
In the present invention, it is preferable to use those having a molecular weight of about 1000 to about 4000.

These perfluoropolyether compounds are hardly soluble in hydrocarbon solvents and alcohol solvents. Therefore, using a lubricant comprising these perfluoropolyether compounds, for example,
When the magnetic recording medium of the present invention is manufactured by the manufacturing method of the present invention, the ratio of the perfluoropolyether compound to the total amount of the lubricant is preferably less than 60% by weight, and more preferably 10 to 10%. 40% by weight.

The lubricant of the present invention may further contain an organic phosphorus compound. In the present invention, the general formula is represented by the above formula (3)
It is preferable to use at least one organic phosphorus compound selected from the group consisting of the organic phosphorus compounds represented by 7) to (45).

In the organic phosphorus compounds represented by the general formulas (37) to (45), the number of carbon atoms n is preferably 8 to 20, and more preferably 12 to 18. When the carbon number n is 21 or more, the solubility in general-purpose solvents such as a hydrocarbon solvent and an alcohol solvent described below tends to decrease. The decrease in solubility in a general-purpose solvent may hinder the production of a magnetic recording medium according to the production method of the present invention, for example, when a lubricant layer of a magnetic recording medium is composed of this composition. When the number of carbon atoms n is 7 or less, the lubricity of the lubricant may decrease.

The proportion of the organic phosphorus compound in the total amount of the lubricant composition is such that the mixing ratio of the fluorine-containing alkylamine of the present invention does not become less than 40% by weight, that is, 6%.
It is preferably less than 0% by weight, more preferably 10 to 40% by weight. Further, when the lubricant is composed of the three components of the fluorinated alkylamine of the present invention, another lubricant and an organic phosphorus compound, the ratio of the fluorinated alkylamine of the present invention is 40% based on the total amount of the lubricant. It is necessary to appropriately determine the content of the other lubricant and the organic phosphorus compound so that the content does not become less than the weight%. The same applies if the lubricant further comprises other components.

The magnetic recording medium of the present invention comprises a ferromagnetic metal film provided on a nonmagnetic support, and a lubricant layer provided on the ferromagnetic metal film via a protective film. Wherein the lubricant layer contains any one of the above lubricants. That is, the lubricant layer contains at least one fluorine-containing alkylamine of the present invention represented by the general formula (46), or at least one fluoropolyether compound in the lubricant. And / or a lubricant further containing at least one organic phosphorus compound. May use any of the lubricants, the amount of the fluorine-containing alkylamine of the present invention contained in the lubricant layer, per surface 1 m ² per lubricant layer 0.0
It is preferably from 5 to 100 mg, more preferably from 0.1 to 50 mg. In order to make such a small amount of the fluorinated alkylamine evenly present in the lubricant layer, the lubricant layer of the magnetic recording medium of the present invention is desirably formed by the following method.

The lubricant layer is formed on the nonmagnetic support by forming a ferromagnetic metal thin film and a protective film in this order using conventional materials and means, and then on the protective film. The step of forming a lubricant layer includes a step of applying a coating solution prepared by dissolving the lubricant of the present invention in a mixed solvent of a hydrocarbon solvent and an alcohol solvent on a protective film, and a step of drying the mixed solvent. including. Eventually the mixed solvent evaporates,
The lubricant dissolved in the solvent remains on the protective film, and forms a lubricant layer. Therefore, even if the coating liquid is applied thickly,
The evaporation of the solvent forms a uniform and very thin lubricant layer on the protective film, that is, a lubricant layer in which a small amount of the lubricant composition uniformly covers the protective film.

The hydrocarbon solvents that can be used in the present invention are, for example, toluene, hexane, heptane, octane, nonane, xylene, ketone, etc. The alcohol solvents that can be used in the present invention are, for example, methyl alcohol, ethyl alcohol, Lower alcohols such as propyl alcohol, isopropyl alcohol and butyl alcohol.
If the proportion of the alcohol-based solvent is too large, coating unevenness is likely to occur. On the other hand, if the proportion of the hydrocarbon-based solvent is too large, it is uneconomical.
It is preferable to use a mixture in a range of 9: 1, preferably in a range of 3: 7 to 7: 3. By using this mixed organic solvent, a lubricant layer having a uniform thickness without coating unevenness and uniformly covering the protective film is formed. As a result, a highly reliable magnetic recording medium having excellent lubrication performance is obtained. Can be

As a method for forming a lubricant layer using the above-mentioned mixed solvent, a wet coating method such as a bar coating method, a gravure coating method, a reverse coating method, a die coating method, a dipping method and a spin coating method, or an organic vapor deposition method And either method may be adopted. After applying the coating solution, a drying process is performed to evaporate the organic solvent, whereby a lubricant layer is formed on the protective film. The drying treatment can be performed by heating or natural drying.

As described above, the magnetic recording medium of the present invention can be formed using conventional materials and processing steps for layers other than the lubricant layer. For example, as the non-magnetic support, a film made of polyethylene terephthalate, polyethylene naphthalate, aromatic polyamide or aromatic polyimide, an aluminum substrate or a glass substrate can be used. In order to achieve both practical reliability and good RF output value, the surface on the nonmagnetic support, that is, the surface in contact with the ferromagnetic metal film, has a diameter of 2 mm.
It is desirable that a projection forming process of 0 to 300 nm and a height of 5 to 40 nm be performed.

The magnetic layer constituting the magnetic recording medium of the present invention is a ferromagnetic metal thin film formed by a method such as ion plating, sputtering or electron beam. Ni-O,
Co, Co-O, Co-Cr, or the like is appropriately selected. The thickness of the magnetic layer is generally 50 nm to 300 nm.

The protective film constituting the magnetic recording medium of the present invention may be an amorphous, graphite or diamond-like carbon thin film obtained by a method such as sputtering or plasma CVD, or a mixture and / or mixture of such carbon. It can be formed using a carbon thin film, a silicon nitride film, or a boron nitride film formed by lamination.

In the present invention, it is particularly preferable to form the protective film with diamond-like carbon, that is, diamond-like carbon. Diamond-like carbon is a most preferable material because it has an appropriate hardness and can suppress damage to a magnetic recording medium and also to a magnetic head. In addition, when forming a thin film using any material, it is preferable that the thickness of a protective film is 3-50 nm.

Although the description has been made above regarding the incorporation of the lubricant containing the fluorinated alkylamine of the present invention into the lubricant layer of the magnetic recording medium, the fluorinated alkylamine of the present invention may also be used, for example, in precision. It can be used as a component of lubricants, surfactants, release agents or rust inhibitors for machines or precision parts.

Hereinafter, the present invention will be described specifically with reference to examples. (First Embodiment) The first embodiment of the present invention relates to the synthesis of a fluorinated alkylamine. The compound synthesized in this example is represented by the following formula (48).

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First, the substance represented by the above formula (48) will be described in comparison with the general formula (46).
₁ is a hexadecyl group having 16 carbon atoms, R ₂ is a fluoroalkyl group having 5 carbon atoms bonded to fluorine, m is 3, n is 2, and a is 3.

Next, a method for producing the substance represented by the above formula (48) will be described. The starting material was 101.3 g of a fluorinated alkylamide ester represented by the following formula (49) (0.11.3 g).
0 mol) and anhydrous tetrahydrofuran (THF) 30
It is 0 milliliter.

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These starting materials are collected in a 1-liter flask equipped with a stirring blade and a dropping funnel, and after flowing dry high-purity nitrogen for 1 minute, the mixture is stirred on a water bath at 15 to 20 ° C. 300 ml of a THF solution of 1M borane THF complex was added dropwise in about 2 hours. Subsequently, the distillation and the stirring were continued for 18 hours to complete the reaction.

After the completion of the reaction, the reaction solution was cooled to 5 to 10 ° C., and 100 ml of distilled water was carefully added dropwise to carry out hydrolysis. Next, 50 milliliters of 6N hydrochloric acid was added, and the reaction solution was heated to 85 to 90 ° C.
After distilling off F, 100 ml of a 6N aqueous sodium hydroxide solution was added dropwise over about 1 hour while continuing reflux and stirring to isolate the amine. Then, the obtained reaction mixture was made into a chloroform solution, and this solution was adjusted to pH 7 with distilled water.
After repeatedly washing until the solution became, the solution was dried with anhydrous boron nitrate.

Next, chloroform was distilled off, and the reaction mixture was converted into a benzene solution. After cooling to 5 ° C., unreacted fluorine-containing alkylamide ester raw materials were removed.
A white solid at 2 ° C. was obtained. This white solid is IR, GPC
By FD-MS, the compound was found to be the compound represented by the above formula (48) without containing starting materials and by-products.

FIG. 1 shows the infrared spectrum of the compound represented by the above formula (48). IR; extinction of absorption peak at 1,640 cm ^-1 of carbonyl group GPC: Fluorine-containing alkylamide ester not detected. FD-MS; main peak at m / e 999.

This example shows an example in which only one of the fluorine-containing alkylamines of the present invention was produced, but various compounds can be synthesized by appropriately changing the starting materials. Can be. For example, by using the substances represented by the following formulas (50) to (55) in place of the fluorine-containing alkylamide ester as a starting material, similarly, other substances represented by the following formulas (56) to (61) can be obtained. Compounds can be produced.

[0052]

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[0053]

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(Second Embodiment) Next, an embodiment of the magnetic recording medium of the present invention will be specifically described.
It is not limited to these examples. In this embodiment, the non-magnetic support of the magnetic recording medium has a thickness of 6.3.
μm, a polyester film was used. This polyester film has several granular projections (average height 7 nm, diameter 1 μm) with a gentle gradient provided by silica fine particles added to the film on the surface, and several particles per 100 μm ^{2 on the} surface, and the polymerization catalyst residue. A relatively large protrusion caused by the fine particles is reduced as much as possible. Further, on the surface of the polyester film, 1 × 10 ⁷ steep ridges per 1 mm ² were provided with silica colloid particles having a diameter of 15 nm as nuclei and an ultraviolet curing epoxy resin as a binder.

A Co—Ni ferromagnetic film (Ni content: 20 mol%, film thickness: 100 nm) was formed on the polyester film by a continuous vacuum oblique deposition method in the presence of a trace amount of oxygen. The oxygen content in the ferromagnetic film was 5% in atomic fraction. Next, plasma CVD is performed on the ferromagnetic film.
By a method, a protective film of diamond-like carbon having a thickness of 5 nm was formed. Subsequently, on the protective film, a coating solution obtained by dissolving a fluorine-containing alkylamine represented by the above formula (48) in a mixed organic solvent of isopropyl alcohol and toluene (weight ratio: 1: 1) was applied using a reverse roll coater. After being applied by a wet coating method, the solvent was evaporated by a drying treatment.

Thus, a lubricant layer containing 10 mg of the fluorine-containing alkylamine per m ² of the surface was finally formed on the protective film. This is cut into a predetermined width to form a magnetic tape, in an environment of 5 ° C and 10% RH, and at 40 ° C and 80%
The vehicle was repeatedly run in a RH environment using a commercially available 8 mm VTR. Then, the output characteristics at that time were measured, and the number of runs until the RF output decreased by 2 dB from the initial value or the output fluctuation started to occur was obtained.

(Third Embodiment) In the magnetic tape of the second embodiment, a magnetic tape was produced using the substance represented by the above formula (56) instead of the substance represented by the above formula (48). A similar test was performed.

(Fourth Embodiment) In the magnetic tape of the second embodiment, instead of the substance represented by the above formula (48), the substance (48) and a conventionally known lubricant C ₁₇ H ₃₃ COOC _{2 are used.}
A similar test was conducted by preparing a magnetic tape using a mixture obtained by mixing H ₄ C ₈ F ₁₇ with H ₄ C ₈ F ₁₇ at a weight ratio of 1: 1.

(Fifth Embodiment) In the magnetic tape of the second embodiment, instead of the substance represented by the above formula (48), the substance (48) and a perfluoropolyether (a commercially available lubricant) were used. Fomblin Z DOL, average molecular weight 2
000: manufactured by Ausimont Co., Ltd.) at a weight ratio of 3: 1 to prepare a magnetic tape using a mixture obtained.
A similar test was performed.

(Sixth Embodiment) In the magnetic tape of the second embodiment, instead of the substance represented by the above formula (48), the substance (48) and a rust inhibitor (C ₁₂ H ₂₅ S) ₃ A magnetic tape was produced using a mixture obtained by mixing P with a 2: 1 weight ratio, and the same test was performed.

FIG. 2 shows the test results of each of the above examples. In FIG. 2, the lubricants of the first conventional example and the second conventional example are substances represented by the above formulas (34) and (35), respectively, and use a coating solution dissolved in a single organic solvent of isopropyl alcohol. Things.

From this, it is clear that all the magnetic tape samples provided with the lubricant layer containing the fluorine-containing alkylamine of the present invention have excellent lubricity under low temperature, low humidity and high temperature, high humidity. On the other hand, it is clear that the lubricating property of the conventional magnetic tape provided with a lubricant layer consisting of only a lubricant significantly decreases under low temperature and low humidity or high temperature and high humidity.

In each of the examples, the material represented by the above formula (48), the material represented by the above formula (56), the material represented by the above formula (48) and a conventionally known lubricant and rust inhibitor Described above, the above formulas (57) to (61)
The same effect was also observed with the substances represented by, and mixtures of these substances with conventionally known lubricants and rust inhibitors.

(Seventh Embodiment) Next, another embodiment of the magnetic recording medium of the present invention will be specifically described. In this embodiment, the non-magnetic support of the magnetic recording medium has a diameter of 95 mm.
A non-magnetic Ni-P alloy plating having a thickness of 25 μm was applied to the surface of an Al alloy plate having a thickness of 1.2 mm and a thickness of 1.2 mm, and a projection having an average roughness of 5 nm and a maximum height of 30 nm was formed by texturing. On the nonmagnetic Ni-P alloy plating of this support, a 130-nm-thick Cr underlayer and a 60-nm-thick Co-Ni ferromagnetic film are formed by a sputtering method, and further, on the ferromagnetic film, A diamond-like carbon protective film having a thickness of 5 nm was formed by a plasma CVD method.

Next, a coating solution obtained by dissolving the fluorine-containing alkylamine represented by the above formula (48) in a mixed organic solvent of isopropyl alcohol and toluene (weight ratio 1: 1) was applied on the protective film. The final amount of fluorine compound is 1 / m ²
A lubricant layer was formed by coating by a wet coating method (dipping method) so that 0 mg was present, thereby producing a magnetic disk.
Then, a CSS (contact start / stop) test was performed on the magnetic disk under the environment of 5 ° C. and 10% RH and the environment of 40 ° C. and 80% RH, and the friction coefficient exceeded 1.0. The durability was determined by measuring the number of CSSs at the time or the number of CSSs at the time of head crash.

(Eighth Embodiment) In the magnetic disk of the seventh embodiment, instead of the substance represented by the above formula (48),
A magnetic disk using the substance represented by the above formula (56) was manufactured, and a similar test was performed.

(Ninth Embodiment) In the magnetic disk of the seventh embodiment, instead of the substance represented by the above formula (48),
A magnetic disk using the same lubricant as in the fourth embodiment was manufactured, and a similar test was performed.

(Tenth Embodiment) The magnetic disk of the seventh embodiment is manufactured by using the same lubricant as that of the fifth embodiment in place of the substance represented by the above formula (48). A similar test was performed.

(Eleventh Embodiment) The magnetic disk of the seventh embodiment is manufactured by using the same lubricant as that of the sixth embodiment in place of the substance represented by the above formula (48). A similar test was performed.

FIG. 3 shows the test results of the above examples. In FIG. 3, the lubricants of the third conventional example and the fourth conventional example are substances represented by the above formulas (34) and (35), respectively, and use a coating solution dissolved in a single organic solvent of isopropyl alcohol. Things.

As a result, all of the magnetic disks provided with a lubricant layer containing at least one kind of the fluorinated alkylamine of the present invention have a large CSS frequency under low temperature and low humidity and high temperature and high humidity, and have excellent durability. You can see that there is. On the other hand, a conventional magnetic disk provided with a lubricant layer consisting of only a lubricant has a small CSS frequency under low temperature and low humidity or high temperature and high humidity, and is clearly inferior in durability.

In the examples, the substance represented by the above formula (48), the substance represented by the above formula (56), and the substance represented by the above formula (4)
Although the mixture of the substance represented by the formula (8) and the conventionally known lubricant and rust inhibitor has been described, the substances represented by the above formulas (57) to (61), and these substances and the conventionally known lubricant,
A similar effect was observed for the mixture with the rust inhibitor.

[0073]

The fluorine-containing alkylamine of the present invention has one amino group, one fluorine-containing terminal group (ie, a fluoroalkyl terminal group having a fluoroalkylene oxide chain) and one fluorine-containing terminal group in one molecule. And an aliphatic hydrocarbon terminal group (that is, an aliphatic alkyl terminal group or an aliphatic alkenyl terminal group). This compound has excellent lubricating properties and is useful as a lubricant for various machines, devices or parts.

For example, a lubricant containing the fluorinated alkylamine of the present invention is lubricated to a magnetic recording medium having a ferromagnetic metal thin film, a protective film and a lubricant layer provided on a non-magnetic support in this order. When contained in the agent layer, due to the synergistic effect of each terminal group contained in the compound of the present invention, excellent lubricity and durability, and lubricity in a wide range of environments from low temperature and low humidity to high temperature and high humidity. A magnetic recording medium that does not decrease can be obtained. This magnetic recording medium is particularly suitable for use in a digital video tape recorder or a high definition video tape recorder.

Further, by further adding a perfluoropolyether-based lubricant and / or an organic phosphorus-based compound to the lubricant layer of the magnetic recording medium, the magnetic recording medium of the present invention has more excellent lubricity and durability. It will be.

Further, by forming the protective film layer of the magnetic recording medium of the present invention from diamond-like carbon, or by forming a nitrogen-containing plasma film on the surface layer of the protective film,
The bonding force between the protective film layer and the lubricant layer is improved, and a more durable magnetic recording medium can be obtained.

The lubricant layer of the magnetic recording medium of the present invention is prepared by dissolving the lubricant composition in a mixed solvent of an alcohol solvent and a hydrocarbon solvent to prepare a coating solution, and applying the coating solution on the protective film. It is formed by coating. The use of this mixed solvent suppresses coating unevenness and enables formation of a thin and uniform lubricant layer.

[Brief description of the drawings]

FIG. 1 is a diagram showing the results of infrared spectroscopic analysis of a fluorinated alkylamine represented by the above formula (48), which is one of the fluorinated alkylamines of the present invention.

FIG. 2 is a diagram showing test results of second to sixth examples.

FIG. 3 is a diagram showing test results of seventh to eleventh examples.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) // C10N 40:18

Claims (18)

[Claims] The general formula is represented by the following formula (1). A fluorine-containing alkylamine represented by the formula: 2. The fluorinated alkylamine according to claim 1, which is used for a lubricant. 3. The general formula is the following formula (2). The fluorinated alkyl amide ester represented by the formula is reduced to give the following general formula (3). A method for producing a fluorinated alkylamine, which obtains a fluorinated alkylamine represented by the formula: 4. The general formula is the following formula (4). A lubricant comprising at least one fluorinated alkylamine represented by the formula: 5. The lubricant according to claim 4, further comprising at least one fluoropolyether compound. 6. The lubricant according to claim 4, further comprising at least one organic phosphorus compound. 7. The organic phosphorus compound has the following general formula (5) to (13): HP (O) (OC _n H _{2n + 1} ) ₂ ... (5) P (OC _n H _{2n + 1} ) _{3 ... (6) P (SC} n H 2n + 1) 3 ... (7) O = P (OC n H 2n + 1) 3 ... (8) S = P (OC n H 2n + 1) 3 ... (9 _{) O = P (SC n H} 2n + 1) 3 ... (10) S = P (SC n H 2n + 1) 3 ... (11) (C n H 2n + 1 O) 2 P (O) OH ... ( 12) (a _{C n H 2n + 1 O)} P (O) (OH) 2 ... (13) a compound selected from the group consisting of organic phosphorus compounds represented by, and the number of carbon atoms is 8 to 20 The lubricant according to claim 6, characterized in that: 8. A magnetic recording medium comprising: a ferromagnetic metal film provided on a nonmagnetic support; and a lubricant layer provided on the ferromagnetic metal film via a protective film. The agent layer contains a lubricant, and the lubricant has the following general formula (14). A magnetic recording medium comprising at least one fluorinated alkylamine represented by the formula: 9. The magnetic recording medium according to claim 8, wherein the lubricant further comprises at least one fluoropolyether compound. 10. The magnetic recording medium according to claim 8, wherein the lubricant further comprises at least one organic phosphorus compound. 11. The organophosphorus compound has the following general formula (15) to (23): HP (O) (OC _n H _{2n + 1} ) ₂ ... (15) P (OC _n H _{2n + 1} ) _{3 ... (16) P (SC} n H 2n + 1) 3 ... (17) O = P (OC n H 2n + 1) 3 ... (18) S = P (OC n H 2n + 1) 3 ... (19 _{) O = P (SC n H} 2n + 1) 3 ... (20) S = P (SC n H 2n + 1) 3 ... (21) (C n H 2n + 1 O) 2 P (O) OH ... ( 22) (a _{C n H 2n + 1 O)} P (O) (OH) 2 ... ( compound selected from the group consisting of organic phosphorus compounds represented by 23), and the number of carbon atoms is 8 to 20 The magnetic recording medium according to claim 10, wherein: 12. The magnetic recording medium according to claim 8, wherein said protective film is made of diamond-like carbon. 13. A method for manufacturing a magnetic recording medium comprising: a ferromagnetic metal film provided on a nonmagnetic support; and a lubricant layer provided on the ferromagnetic metal film via a protective film. The lubricant layer contains a lubricant, and the lubricant has the following general formula (24). The lubricant layer forming step comprises dissolving the lubricant in a mixed organic solvent of a hydrocarbon-based solvent and an alcohol-based solvent. A method for manufacturing a magnetic recording medium, comprising a step of coating the protective film. 14. The lubricant according to claim 1, wherein the lubricant further comprises at least one fluoropolyether compound.
3. The method for manufacturing a magnetic recording medium according to item 3. 15. The lubricant according to claim 13, wherein the lubricant further comprises at least one organic phosphorus compound.
3. The method for manufacturing a magnetic recording medium according to claim 1. 16. The organic phosphorus compound has the following general formula (25) to (33): HP (O) (OC _n H _{2n + 1} ) ₂ ... (25) P (OC _n H _{2n + 1} ) _{3 ... (26) P (SC} n H 2n + 1) 3 ... (27) O = P (OC n H 2n + 1) 3 ... (28) S = P (OC n H 2n + 1) 3 ... (29 _{) O = P (SC n H} 2n + 1) 3 ... (30) S = P (SC n H 2n + 1) 3 ... (31) (C n H 2n + 1 O) 2 P (O) OH ... ( 32) (a _{C n H 2n + 1 O)} P (O) (OH) 2 ... (33) a compound selected from the group consisting of organic phosphorus compounds represented by, and the number of carbon atoms is 8 to 20 The method for manufacturing a magnetic recording medium according to claim 15, wherein: 17. The method according to claim 13, wherein the protective film is made of diamond-like carbon. 18. The method according to claim 17, wherein the mixing ratio of the hydrocarbon solvent and the alcohol solvent is in the range of 1: 9 to 9: 1 by weight. .