JPH01199321A - Production of information recording medium, information recording medium, information recording device and fluorine-contained isocyanate derivative - Google Patents
Production of information recording medium, information recording medium, information recording device and fluorine-contained isocyanate derivativeInfo
- Publication number
- JPH01199321A JPH01199321A JP2195688A JP2195688A JPH01199321A JP H01199321 A JPH01199321 A JP H01199321A JP 2195688 A JP2195688 A JP 2195688A JP 2195688 A JP2195688 A JP 2195688A JP H01199321 A JPH01199321 A JP H01199321A
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- recording medium
- information recording
- containing isocyanate
- isocyano group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000012948 isocyanate Substances 0.000 title claims abstract description 69
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 64
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims abstract description 33
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 239000000758 substrate Substances 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 63
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 62
- 239000011737 fluorine Substances 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 43
- -1 isocyanate compound Chemical class 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 229920006254 polymer film Polymers 0.000 claims description 2
- 230000008929 regeneration Effects 0.000 claims description 2
- 238000011069 regeneration method Methods 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 abstract description 27
- 230000001050 lubricating effect Effects 0.000 abstract description 18
- 230000007547 defect Effects 0.000 abstract description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 4
- 125000006239 protecting group Chemical group 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 230000007423 decrease Effects 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 230000001172 regenerating effect Effects 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000010702 perfluoropolyether Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000006247 magnetic powder Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 229910052594 sapphire Inorganic materials 0.000 description 2
- 239000010980 sapphire Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- QAEKNCDIHIGLFI-UHFFFAOYSA-L cobalt(2+);2-ethylhexanoate Chemical compound [Co+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QAEKNCDIHIGLFI-UHFFFAOYSA-L 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- FYJQJMIEZVMYSD-UHFFFAOYSA-N perfluoro-2-butyltetrahydrofuran Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C1(F)F FYJQJMIEZVMYSD-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000005143 pyrolysis gas chromatography mass spectroscopy Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Magnetic Record Carriers (AREA)
- Manufacturing Of Magnetic Record Carriers (AREA)
- Lubricants (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、磁気ディスク、磁気テープ、磁気カード、磁
気ドラム等の情報記録媒体の潤滑膜等に用いる含フッ素
イソシアネート重合膜の形成方法およびその原材料であ
る含フッ素イソシアネート誘導体並びにこの情報記録媒
体を用いた情報記録装置に関する。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a method for forming a fluorine-containing isocyanate polymer film used as a lubricating film for information recording media such as magnetic disks, magnetic tapes, magnetic cards, and magnetic drums, and a method thereof. The present invention relates to a fluorine-containing isocyanate derivative as a raw material and an information recording device using this information recording medium.
一般に磁気記録媒体の表面は、記録再生時に磁気記録ヘ
ッド等により摩擦される。この摩擦による性能低下を防
止するために、磁気記録媒体表面に潤滑膜を形成する方
法が一般に知られている。Generally, the surface of a magnetic recording medium is rubbed by a magnetic recording head or the like during recording and reproduction. In order to prevent performance deterioration due to this friction, a method of forming a lubricating film on the surface of a magnetic recording medium is generally known.
当技術分野において、ペルフルオロポリエーテル等の含
フッ素化合物を潤滑膜材料として使用することは、公知
であり、ペルフルオロポリエーテルの末端にイソシアノ
基を導入した化合物も知られている（米国特許第３８１
０８７４号）。In the technical field, it is known to use fluorine-containing compounds such as perfluoropolyether as lubricating film materials, and compounds in which isocyano groups are introduced at the terminals of perfluoropolyether are also known (US Pat. No. 381)
No. 0874).
また、磁気記録媒体の潤滑剤として含フッ素イソシアネ
ートを用いること（特開昭６２−１４５５３ ）、およ
びイソシアネートと多価アルコールより生成する含フッ
素ポリウレタンを用いること（特開昭６２−１８７７９
８）が知られている。Furthermore, fluorine-containing isocyanate is used as a lubricant for magnetic recording media (Japanese Patent Laid-Open No. 62-14553), and fluorine-containing polyurethane produced from isocyanate and polyhydric alcohol is used (Japanese Patent Laid-Open No. 62-18779).
8) is known.
さらに、イソシアネートは、フェノール、アルコール等
の活性水素化合物と付加物をつくり、水分に対して安定
化されることが知られている（０．Ｂａｙａｒ Ａｎｇ
ａｖ、Ｃｈｅ＋ｍ、、 Ａ５９，２６５（１９４７））
ａ〔発明が解決しようとする課題〕
上記従来技術は、含フッ素イソシアネートを磁気記録媒
体の潤滑膜に適用する際の製造プロセスの安定性につい
ては配慮されていない、すなわち、含フッ素イソシアネ
ートはポットライフが短く、磁気記録媒体の潤滑剤とし
て含フッ素イソシアネートを用いた場合、ポットライフ
の切れたものを使うと潤滑剤固型物の付着による潤滑膜
の欠陥発生等の解決すべき課題があった。Furthermore, it is known that isocyanates form adducts with active hydrogen compounds such as phenol and alcohol, and are stabilized against moisture (0. Bayar Ang
av, Che+m, A59, 265 (1947))
a [Problems to be Solved by the Invention] The above-mentioned prior art does not consider the stability of the manufacturing process when applying fluorine-containing isocyanates to the lubricating film of magnetic recording media. When a fluorine-containing isocyanate is used as a lubricant for a magnetic recording medium, there are problems that need to be solved, such as defects in the lubricant film due to adhesion of lubricant solids when a fluorine-containing isocyanate is used as a lubricant for magnetic recording media.
本発明の目的は、欠陥発生の少ないプロセス安定性に優
れた磁気記録媒体の潤滑膜形成方法を提供することにあ
る。An object of the present invention is to provide a method for forming a lubricating film on a magnetic recording medium that has less defects and excellent process stability.
上記目的は、含フッ素イソシアネートのイソシアノ基を
保護した含フッ素イソシアネート誘導体を潤滑剤として
用い、媒体面へ付着した後、加熱処理によりイソシアノ
基を再生し、引き続き重合させることにより達成できる
。The above object can be achieved by using a fluorinated isocyanate derivative in which the isocyano group of the fluorinated isocyanate is protected as a lubricant, and after adhering to the medium surface, the isocyano group is regenerated by heat treatment, and then polymerized.
含フッ素イソシアネートを磁気記録媒体の潤滑剤として
用いた時、ポットライフが短いばかりでなく、潤滑膜の
欠陥発生等の問題があったが、上記問題点を解決すべく
鋭意研究を行ったところ。When fluorine-containing isocyanate is used as a lubricant for magnetic recording media, there are problems such as short pot life and defects in the lubricating film.We have conducted extensive research to solve these problems.
空気中の水分により、含フッ素イソシアネートが加水分
解や重合するためであることがわかった。It turns out that this is because the fluorine-containing isocyanate is hydrolyzed and polymerized by moisture in the air.
そこで、加水分解や重合を防ぐため、含フッ素イソシア
ネートのイソシアノ基を一時的に保護することにした。Therefore, in order to prevent hydrolysis and polymerization, we decided to temporarily protect the isocyano groups of the fluorinated isocyanate.
また、イソシアノ基の保護は炭化水素系のイソシアネー
ト化合物で知られているが、含フッ素イソシアネート化
合物は、炭化水素系のイソシアネート化合物とは、反応
試薬との反応性、相溶性等が異なり１合成が困難である
為、未だ合成例はない。In addition, protection of isocyano groups is known with hydrocarbon-based isocyanate compounds, but fluorine-containing isocyanate compounds differ from hydrocarbon-based isocyanate compounds in terms of reactivity and compatibility with reaction reagents, making it difficult to synthesize. Due to the difficulty, there are no examples of synthesis yet.
本発明者らは合成方法を検討し、含フッ素イソシアネー
トのイソシアノ基を保護した誘導体を得た。The present inventors investigated a synthetic method and obtained a derivative in which the isocyano group of a fluorine-containing isocyanate was protected.
本発明による上記誘導体を磁気記録媒体の潤滑剤として
用いるとポットライフが長くなり、欠陥発生が低減する
が、さらに摺動特性が改善される効果もあることがわか
った。摺動特性が改善されるのは含フッ素イソシアネー
トの架橋密度が上がったためと思われる。It has been found that when the above-mentioned derivative according to the present invention is used as a lubricant for magnetic recording media, the pot life becomes longer and the occurrence of defects is reduced, and the sliding properties are further improved. The improvement in sliding properties is thought to be due to the increased crosslinking density of the fluorine-containing isocyanate.
本発明の潤滑剤は、イソシアノ基がアルコール。 In the lubricant of the present invention, the isocyano group is alcohol.
フェノール等の活性水素化合物よりなる保護基で保護さ
れているので、基板への付着時は、水分に対して安定で
あり、その後、加熱処理により保護基が解離されてイソ
シアノ基は再生し、再生された含フッ素イソシアネート
は、加水分解、重合して所望の潤滑膜となる。Since it is protected with a protecting group made of an active hydrogen compound such as phenol, it is stable against moisture when attached to a substrate, and then the protecting group is dissociated by heat treatment and the isocyano group is regenerated. The resulting fluorine-containing isocyanate is hydrolyzed and polymerized to form a desired lubricating film.
本発明の磁気記録媒体の潤滑膜形成方法において潤滑剤
として使用される含フッ素イソシアネートは、フルオロ
ポリエーテル鎖あるいはフルオロアルキル鎖を基本構造
とし、イソシアノ基を少なくとも１つ以上有する化合物
のなかから選ばれる。The fluorine-containing isocyanate used as a lubricant in the method for forming a lubricant film on a magnetic recording medium of the present invention is selected from compounds having a basic structure of a fluoropolyether chain or a fluoroalkyl chain and having at least one isocyano group. .
上記フルオロポリエーテル鎖あるいはフルオロアルキル
鎖は、直鎖状のものばかりでなく、分岐したものでもか
まわない、上記含フッ素イソシアネートとしては、例え
ば、
０ＣＮＧＨｚ［（ＣＦｚＯ）ｎ（ＣＦｘＣＦｚＯ）−］
ＧＨｚＮＣＯＯＣＮ［（ＣＦｚＯ）ｎ（ＣＦｚＣＦｚＯ
）、コＮＣ０Ｃ７Ｆｔｓ（ＣＨｚ）ｘｘＮｃ。The fluoropolyether chain or fluoroalkyl chain may be not only a linear chain but also a branched chain. Examples of the fluorine-containing isocyanate include 0CNGHz[(CFzO)n(CFxCFzO)-]
GHzNCOOCN[(CFzO)n(CFzCFzO
), KONC0C7Fts(CHz)xxNc.
などがある。and so on.
これらの含フッ素イソシアネートのイソシアノ基（−Ｎ
ＧＯ）を保護するために使用する化合物としては、アル
コール、フェノール、ジケトン。The isocyano group (-N
Compounds used to protect GO) include alcohols, phenols, and diketones.
カルボン酸ジエステル、複素環化合物等があげられ、具
体的にはメタノール、エタノール、ｔ−ブチルアルコー
ル、ｍ−クレゾール、アセチルアセトン、マロン酸ジエ
ステル、エチレンジイミン。Examples include carboxylic acid diesters, heterocyclic compounds, etc., specifically methanol, ethanol, t-butyl alcohol, m-cresol, acetylacetone, malonic acid diesters, and ethylenediimine.
アセト酢酸エステル、ピロール、ベンゾトリアゾールな
どがある。Examples include acetoacetate, pyrrole, and benzotriazole.
上記化合物を用いて、例えば次の反応によりイソシアノ
基の保護が可能である。Using the above compounds, it is possible to protect isocyano groups, for example, by the following reaction.
０ＣＮ−Ｒｆ−ＮＣＯ＋２’ＢｕＯＨ−４ｔＢｕＯｃＮ
ＣＯＭｅ Ｍ
０ＣＮ−Ｒｆ−ＮＧＯ＋２ＣＨｚ →＼
ＣＯＭｅ Ｍ
ＣＯ念Ｅｔ Ｅｔ
０ＣＮ−Ｒｆ−ＮＧＯ＋２ＣＨｚ →＼
Ｃ０ｚＥ ｔ Ｅ ｔ
ＮＨＣＣＨ
＼
０ｚＥｔ
Ｈ−Ｒｆ−ＮＨＣＯｔＢｕ
ｅＯＣＣＯＭａ
ＣＯ
（ただし、−Ｒｆ−：フッ素原子を含む２価の有機基、
Ｍｅ；メチル基、Ｅｔ；エチル基、’Ｂｕ；第３ブチル
基）。0CN-Rf-NCO+2'BuOH-4tBuOcN
COMe M 0CN-Rf-NGO+2CHz →\COMe M COEt Et 0CN-Rf-NGO+2CHz →\ C0zE t Et NHCCH \ 0zEt H-Rf-NHCOtBu eOCCOMa CO ( However, -Rf-: divalent containing a fluorine atom organic group,
Me: methyl group, Et: ethyl group, 'Bu: tertiary butyl group).
以上、分子中にイソシアノ基を２つ有する含フッ素イソ
シアネートについて例示したが、イソシアノ基を１つあ
るいは３つ以上有する化合物についても、同様の方法で
イソシアノ基を保護できることは、いうまでもない。Although fluorine-containing isocyanates having two isocyano groups in the molecule have been exemplified above, it goes without saying that the isocyano groups of compounds having one or three or more isocyano groups can also be protected in the same manner.
上記反応における反応溶媒として、フッ素系溶媒および
炭化水素系溶媒の混合溶媒を使用してもかまわない。As the reaction solvent in the above reaction, a mixed solvent of a fluorine-based solvent and a hydrocarbon-based solvent may be used.
フッ素系溶媒としては、フルオロカーボン類。Fluorocarbons are examples of fluorine-based solvents.
フルオロクロロカーボン類等が挙げられ、具体的には、
トリクロロトリフルオロエタン、ペルフルオロ−２−ブ
チルテトラヒドロフラン、ペルフルオロへブタン等があ
る。Examples include fluorochlorocarbons, specifically,
Examples include trichlorotrifluoroethane, perfluoro-2-butyltetrahydrofuran, and perfluorohebutane.
炭化水素系溶媒としては、エーテル、炭化水素等が挙げ
られ、具体的には、ジエチルエーテル。Examples of hydrocarbon solvents include ethers and hydrocarbons, specifically diethyl ether.
ジエチレングリコールジメチルエーテル、テトラヒドロ
フラン、ベンゼン、トルエン等がある。Examples include diethylene glycol dimethyl ether, tetrahydrofuran, benzene, and toluene.
反応・に際しては、上記溶媒を単独あるいは混合溶媒と
して使用する他に、反応物をそれぞれフッ素系、炭化水
素系溶媒に別々に溶解し、溶液のかたちで反応させる方
法等もある。In the reaction, in addition to using the above-mentioned solvents alone or as a mixed solvent, there is also a method of separately dissolving the reactants in a fluorine-based solvent and a hydrocarbon-based solvent and reacting them in the form of a solution.
含フッ素イソシアネートと保護剤は、反応系の乾燥状態
、攪拌状態等により多少の変動があるが、はぼ化学量論
的に反応する。The fluorine-containing isocyanate and the protective agent react approximately stoichiometrically, although there is some variation depending on the drying state of the reaction system, stirring state, etc.
したがって、各化合物の仕込み比は、当量比で０．５〜
２倍の範囲にあるのが、未反応物の除去の点から考えて
好適である。Therefore, the charging ratio of each compound is from 0.5 to 0.5 in terms of equivalent ratio.
A range of 2 times is preferable from the viewpoint of removing unreacted substances.
上記反応において、カリウム第３ブトキシド。In the above reaction, potassium tert-butoxide.
トリエチルアミン、ジブチルビス（ラウリナト）スズ、
２−エチルへキサン酸コバルト等の触媒を用いてもかま
わない。triethylamine, dibutylbis(laurinato)tin,
A catalyst such as cobalt 2-ethylhexanoate may also be used.
触媒の添加量は、含フッ素イソシアネートに対し、１０
−１〜１〇一番当量で十分である。The amount of catalyst added is 10% to fluorine-containing isocyanate.
-1 to 10 most equivalent is sufficient.
反応生成物の精製法としては、抽出、蒸留、液体クロマ
トグラフィ等の周知の方法を適用できる。As a method for purifying the reaction product, well-known methods such as extraction, distillation, and liquid chromatography can be applied.
上記反応で合成した含フッ素イソシアネート誘導体を磁
気記録媒体に適用する際には、直接あるいは、溶液の状
態にして、スプレー・ワイプ法。When applying the fluorine-containing isocyanate derivative synthesized by the above reaction to a magnetic recording medium, the spray-wipe method is used, either directly or in the form of a solution.
デイツプ法、スピンコード法等により付着される。It is attached by dip method, spin code method, etc.
媒体面に付着された含フッ素イソシアネート誘導体は、
加熱によりイソシアノ基を再生し、媒体面上で重合する
。The fluorine-containing isocyanate derivative attached to the medium surface is
The isocyano groups are regenerated by heating and polymerized on the medium surface.
イソシアノ基の再生および重合に要する温度は含フッ素
イソシアネート誘導体の種類によって異なるが、低温で
は反応が遅く、高温では媒体の劣化が起こりやすいので
一般に１００〜２００℃の範囲であることが好ましい。The temperature required for regeneration and polymerization of isocyano groups varies depending on the type of fluorine-containing isocyanate derivative, but is generally preferably in the range of 100 to 200°C, since the reaction is slow at low temperatures and the medium tends to deteriorate at high temperatures.
なお、本発明においては、イソシアノ基を水に対して保
護した含フッ素イソシアネート誘導体を使用する点が重
要であり、上記誘導体を前述の反応とは異なる別の方法
で合成した化合物を使用してもかまわない。In addition, in the present invention, it is important to use a fluorine-containing isocyanate derivative whose isocyano group is protected from water, and it is also possible to use a compound synthesized from the above derivative by a different method different from the above-mentioned reaction. I don't mind.
まず含フッ素イソシアネート誘導体合成の実施例を実施
例１〜４に示す。First, examples of synthesis of fluorine-containing isocyanate derivatives are shown in Examples 1 to 4.
実施例１
式（１）で示されるペルフルオロポリエーテル−α、ω
−ジカルボキシアミドトリレンイソシアネート（平均分
子量２０００）２０ｇ
を１，１．２−トリフルオロトリクロロエタン（以下フ
レオンと略称）１００ｍｍに溶解した。Example 1 Perfluoropolyether represented by formula (1) - α, ω
-20 g of dicarboxamide tolylene isocyanate (average molecular weight: 2000) was dissolved in 100 mm of 1,1.2-trifluorotrichloroethane (hereinafter abbreviated as Freon).
上記溶液を無水硫酸マグネシウムで乾燥後、第３ブチル
アルコール２ｇを加え、６時間還流した。After drying the above solution over anhydrous magnesium sulfate, 2 g of tertiary butyl alcohol was added and the mixture was refluxed for 6 hours.
反応終了後、溶媒および未反応の第３ブチルアルコール
を減圧下で留去し、式（２）の化合物を得た。After the reaction was completed, the solvent and unreacted tertiary butyl alcohol were distilled off under reduced pressure to obtain the compound of formula (2).
・・・（２）
赤外スペクトルでは、２２７０ａｍ″″ｌのＮＧＯ基に
よる吸収が消失した。...(2) In the infrared spectrum, the absorption by the NGO group at 2270 am""l disappeared.
ＩＨ−ＨＭＲスペクトルでは、１．２〜１．８ｐｐｍに
’Ｂｕ のプロトンによる吸収が観測された。In the IH-HMR spectrum, absorption due to 'Bu protons was observed at 1.2 to 1.8 ppm.
以上の分析結果は、上記構造を支持するものである。The above analysis results support the above structure.
実施例２
式（１）の含フッ素イソシアネートを２０ｇ含むフレオ
ン溶液１００ｍＭを無水硫酸マグネシウムで乾燥した。Example 2 A 100 mM Freon solution containing 20 g of the fluorine-containing isocyanate of formula (1) was dried over anhydrous magnesium sulfate.
上記溶液にｍ−クレゾール５ｇを加え、約１２時間還流
した。5 g of m-cresol was added to the above solution, and the mixture was refluxed for about 12 hours.
反応終了後、溶媒を留去し、ベンゼンで洗浄後。After the reaction was completed, the solvent was distilled off and washed with benzene.
乾燥して式（３）の化合物を得た。After drying, a compound of formula (3) was obtained.
ｌｅ
赤外スペクトルでは、２２７０ｃｎ″″１のＮＧＯ基に
よる吸収が消失した。In the le infrared spectrum, the absorption due to the NGO group at 2270cn''1 disappeared.
熱分解ガスクロマトグラフィー質量分析の結果。Results of pyrolysis gas chromatography mass spectrometry.
ｍ−クレゾールに対応するｍ／Ｑ＝１０８．１４のピー
クが観測された。A peak at m/Q=108.14 corresponding to m-cresol was observed.
以上の分析結果は、上記構造を支持するものである。The above analysis results support the above structure.
実施例３
式（１）の含フッ素イソシアネートを２０ｇ含むフレオ
ン溶液１００ｍＱを無水硫酸マグネシウムで乾燥した、
上記溶液に、カリウム−ｔ−ブトキシド３ｇ、マロン酸
ジエチル５ｇを含むテトラヒドロフラン溶液５０ｍＡを
乾燥窒素雰囲気下で加え、６時間攪拌した。Example 3 100 mQ of a Freon solution containing 20 g of the fluorine-containing isocyanate of formula (1) was dried over anhydrous magnesium sulfate.
To the above solution, 50 mA of a tetrahydrofuran solution containing 3 g of potassium t-butoxide and 5 g of diethyl malonate was added under a dry nitrogen atmosphere, and the mixture was stirred for 6 hours.
反応終了後、減圧下で溶媒を留去し、無水エタノールで
洗浄後、乾燥して式（４）の化合物を得た。After the reaction was completed, the solvent was distilled off under reduced pressure, washed with anhydrous ethanol, and dried to obtain a compound of formula (4).
赤外スペクトルでは、２２７０ｃｍ−”のＮＧＯ基によ
る吸収が消失した。In the infrared spectrum, the absorption by the NGO group at 2270 cm-'' disappeared.
ＡＨ−ＨＭＲスペクトルでは、δ＝１．１〜１ 、５
ｐｐｍにエチル基のメチルプロトン、δ＝４．０〜４
、６ ｐｐｍにエチル基のメチレンプロトンが観測され
た。In the AH-HMR spectrum, δ=1.1~1,5
Methyl proton of ethyl group in ppm, δ = 4.0-4
, 6 ppm, a methylene proton of the ethyl group was observed.
以上の分析結果は、上記構造を支持するものである。The above analysis results support the above structure.
実施例４
実施例３におけるマロン酸ジエチルのかわりにアセチル
アセトン３ｇを用い、式（５）の化合物を得た。Example 4 Using 3 g of acetylacetone instead of diethyl malonate in Example 3, a compound of formula (5) was obtained.
赤外スペクトルでは、２２７０ａｍ−”のＮＧＯ基によ
る吸収が消失した。In the infrared spectrum, the absorption by the NGO group at 2270 am-'' disappeared.
ＩＨ−ＨＭＲスペクトルでは、δ＝２．１〜署
２ 、６ ｐｐｍにＣＨｓ Ｃ−のプロトンが観測され
た。In the IH-HMR spectrum, protons of CHs C- were observed at δ = 2.1 ~ 2, 6 ppm.
以上の分析結果は、上記構造を支持するものである。The above analysis results support the above structure.
上記式（１）の含フッ素イソシアネートおよび式（２）
〜（５）の含フッ素イソシアネート誘導体の構造式を表
１にまとめて示す。Fluorine-containing isocyanate of the above formula (1) and formula (2)
The structural formulas of the fluorine-containing isocyanate derivatives of (5) to (5) are summarized in Table 1.
次に磁気記録媒体の製造方法の実施例を実施例５〜１４
に示す。Next, Examples 5 to 14 of the method for manufacturing a magnetic recording medium will be described.
Shown below.
実施例５
磁気記録媒体として、エポキシ、フェノールおよびポリ
ビニルブチラール樹脂よりなるバインダ中に磁性粉（γ
−Ｆｅｚｅｓ）を分散させて作製した５インチ径の塗布
型磁気ディスクに式（２）の含フッ素イソシアネート誘
導体のｏ、ｓＣ’＞ｖ％フレオン溶液をスプレ塗布した
。Example 5 As a magnetic recording medium, magnetic powder (γ
A solution of o, sC'>v% freon of the fluorine-containing isocyanate derivative of formula (2) was spray-coated onto a 5-inch-diameter coated magnetic disk prepared by dispersing -Fezes).
ついで、この磁気ディスクを２００℃で２時間加熱し、
潤滑膜とした。Next, this magnetic disk was heated at 200°C for 2 hours,
It was used as a lubricating film.
上記磁気ディスクを用い、ピエゾ素子をアームにとりつ
けた磁気ヘッドを０．２ μｍの高さで浮上させ、ピエ
ゾ素子の平均出力ノイズレベルの５倍を越えるピーク数
を潤滑膜の欠陥数とした。なお、ノイズと欠陥を分離し
て測定するために、上記方法では、平均出力ノイズレベ
ルの５倍以上のピークに限定している。Using the above magnetic disk, a magnetic head with a piezo element attached to the arm was levitated at a height of 0.2 μm, and the number of peaks exceeding five times the average output noise level of the piezo element was defined as the number of defects in the lubricant film. Note that in order to measure noise and defects separately, the above method is limited to peaks that are five times or more the average output noise level.
潤滑剤溶液調製時から、それぞれ１時間、１０日間、１
ケ月経過した潤滑剤溶液で試作した試料について欠陥数
を求めた結果を表２に示す。1 hour, 10 days, and 1 hour from the time of lubricant solution preparation, respectively.
Table 2 shows the results of determining the number of defects for samples made using lubricant solutions that have been used for several months.
なお、ロット数は１０００であり、潤滑膜厚は約１００
人である。The number of lots is 1000, and the lubricant film thickness is approximately 100.
It's a person.
実施例６
含フッ素イソシアネート誘導体として式（３）の化合物
を用い、実施例５と同様の方法で行った。Example 6 The same method as in Example 5 was carried out using the compound of formula (3) as the fluorine-containing isocyanate derivative.
実施例７
含フッ素イソシアネート誘導体として式（４）の化合物
を用い、実施例５と同様の方法で行った。Example 7 The same method as in Example 5 was carried out using the compound of formula (4) as the fluorine-containing isocyanate derivative.
実施例８
含フッ素イソシアネート誘導体として式（５）の化合物
を用い、実施例５と同様の方法で行った。Example 8 The same method as in Example 5 was carried out using the compound of formula (5) as the fluorine-containing isocyanate derivative.
比較例１
含フッ素イソシアネート誘導体のかわりに式（１）の含
フッ素イソシアネートを用い、実施例５と同様の方法で
行った。Comparative Example 1 The same method as in Example 5 was carried out using the fluorine-containing isocyanate of formula (1) instead of the fluorine-containing isocyanate derivative.
実施例６〜８および比較例１における試験結果を実施例
５の結果と同じく表２に示す。The test results in Examples 6 to 8 and Comparative Example 1 are shown in Table 2 as well as the results in Example 5.
実施例９
磁気記録媒体として、ＮｉＰをメツキしたへΩ合金基板
上に、Ａｒガス雰囲気中の高周波スパッタリング法によ
り、膜厚０．２５ μｍのＣｒ、膜厚０．０６ ｐｍ
のＧｏ−Ｎｉ−Ｚｒ金属磁性膜、膜厚０．０５ μｍの
炭素保護膜を順次形成した磁気ディスクを用い、含フッ
素イソシアネート誘導体として式（４）の化合物を用い
て、実施例５と同様の方法で試料を作製した。欠陥数を
求めた結果を表３に示す。Example 9 As a magnetic recording medium, a Cr film with a thickness of 0.25 μm and a film with a thickness of 0.06 pm were deposited on a NiP-plated Hemega alloy substrate by high-frequency sputtering in an Ar gas atmosphere.
Using a magnetic disk on which a Go-Ni-Zr metal magnetic film and a carbon protective film with a thickness of 0.05 μm were sequentially formed, and using the compound of formula (4) as the fluorine-containing isocyanate derivative, the same procedure as in Example 5 was carried out. A sample was prepared using the method. Table 3 shows the results of determining the number of defects.
実施例１０
含フッ素イソシアネート誘導体として式（５）の化合物
を用い、実施例９と同様の方法で行った。Example 10 The same method as in Example 9 was carried out using the compound of formula (5) as the fluorine-containing isocyanate derivative.
比較例２
含フッ素イソシアネート誘導体のかわりに式（１）の含
フッ素イソシアネートを用い、実施例９と同様の方法で
行った０本比較例における試験結果を表３に示す。Comparative Example 2 Table 3 shows the test results in a comparative example in which the fluorine-containing isocyanate of formula (1) was used in place of the fluorine-containing isocyanate derivative and the same method as in Example 9 was conducted.
実施例１１
実施例９と同様の方法で作製した磁気ディスクを式（２
）の含フッ素イソシアネート誘導体の０．５温シＶ％フ
レオン溶液に浸した後、引き上げデイツプ塗布した。Example 11 A magnetic disk manufactured in the same manner as in Example 9 was prepared using the formula (2
) was immersed in a 0.5-warm V% Freon solution of the fluorine-containing isocyanate derivative, and then pulled up and coated with a dip.
ついで、この磁気ディスクを２００℃で２時間加熱し、
潤滑膜とした。Next, this magnetic disk was heated at 200°C for 2 hours,
It was used as a lubricating film.
欠陥数は、実施例５と同様の方法で求めた。結果を表４
に示す。The number of defects was determined in the same manner as in Example 5. Table 4 shows the results.
Shown below.
実施例１２
式（３）の含フッ素イソシアネート誘導体を用い、実施
例１１と同様の方法で行った。Example 12 The same method as in Example 11 was carried out using the fluorine-containing isocyanate derivative of formula (3).
実施例１３ 式（４）の含フッ素イソシアネート誘導体を用い。Example 13 Using a fluorine-containing isocyanate derivative of formula (4).
実施例１１と同様の方法で行った。The same method as in Example 11 was used.
実施例１４
式（５）の含フッ素イソシアネート誘導体を用い、実施
例９と同様の方法で行った。Example 14 The same method as in Example 9 was carried out using the fluorine-containing isocyanate derivative of formula (5).
比較例３
含フッ素イソシアネート誘導体のかわりに、式（１）の
含フッ素イソシアネートを用い、実施例９と同様の方法
で行った。Comparative Example 3 The same method as in Example 9 was carried out using the fluorine-containing isocyanate of formula (1) instead of the fluorine-containing isocyanate derivative.
実施例１０〜１４および比較例３における試験結果を実
施例９の結果と同じく表４に示す。The test results in Examples 10 to 14 and Comparative Example 3 are shown in Table 4 as well as the results in Example 9.
以上の実施例１〜１４および比較例１〜３から次のこと
がわかる。The following can be seen from the above Examples 1 to 14 and Comparative Examples 1 to 3.
表２から明白であるように、スプレ塗布により潤滑膜を
形成した場合１本発明の方法（実施例５〜８）に較べ、
含フッ素イソシアネートを用いる従来法（比較例１）で
は、１０日後には欠陥数が１桁以上、１ケ月後には、さ
らに増大している。As is clear from Table 2, when a lubricant film is formed by spray coating, compared to the method of the present invention (Examples 5 to 8),
In the conventional method (Comparative Example 1) using a fluorine-containing isocyanate, the number of defects increased by one digit or more after 10 days, and further increased after 1 month.
イソシアノ基を保護した化合物を用いる本発明の方法に
よって、長期にわたって欠陥数の少ない安定なプロセス
が得られる。The method of the present invention using compounds with protected isocyano groups provides a stable process with a low number of defects over a long period of time.
また、表３の比較例２および実施例９，１０から明白で
あるように、本発明による方法は、塗布型磁性膜ばかり
でなく、金属磁性膜に対しても有効である。Further, as is clear from Comparative Example 2 and Examples 9 and 10 in Table 3, the method according to the present invention is effective not only for coated magnetic films but also for metal magnetic films.
また、表４の比較例３および実施例１１〜１４に見られ
るように、本発明による方法は、スプレー塗布ばかりで
なく、デイツプ塗布に対しても有効である。Further, as seen in Comparative Example 3 and Examples 11 to 14 in Table 4, the method according to the present invention is effective not only for spray coating but also for dip coating.
さらには、式（１）〜（５）の化合物の２′８″／１％
フレオン溶液を調製し、湿度ＲＨ６０％（２７℃）の空
気を封入し、２７℃で放置する実験を行なった結果、イ
ソシアノ基を保護しない式（１）の化合物は、２週間後
、固体不溶物が生成したのに対し、イソシアノ基を保護
した本発明の実施例１〜４にて得られた式（１）〜（５
）の化合物は、１ケ月放置後も、固体不溶物が生成せず
安定であり、潤滑剤として用いた場合経時変化が小さく
有効であることがわかった。Furthermore, 2'8''/1% of the compounds of formulas (1) to (5)
As a result of an experiment in which a Freon solution was prepared, air with a humidity of 60% RH (27°C) was sealed, and the mixture was left at 27°C, the compound of formula (1), which does not protect the isocyano group, became a solid insoluble after two weeks. was generated, whereas formulas (1) to (5) obtained in Examples 1 to 4 of the present invention in which the isocyano group was protected
It was found that the compound of ) is stable without forming solid insoluble matter even after being left for one month, and when used as a lubricant, it shows little change over time and is effective.
以上の実施例および比較例では、膜厚１００人の潤滑膜
を形成する際の欠陥数について示したが、これ以外の膜
厚を形成する際にも、同様の結果が得られた。In the above Examples and Comparative Examples, the number of defects was shown when forming a lubricating film with a thickness of 100 people, but similar results were obtained when forming a film with a thickness other than this.
なお上記比較例１〜３および実施例５〜１４では、潤滑
剤塗布前にφ＝０．２ μｍのフィルタでろ過を行って
いる。このため、比較例１〜３の欠陥数は、３割はど小
さい値となっている。ろ過により、潤滑剤固型物は、あ
る程度除去され、欠陥数が低減するが、本発明のように
イソシアノ基を保護した時はど効果的ではない。In Comparative Examples 1 to 3 and Examples 5 to 14, filtration was performed using a filter with a diameter of 0.2 μm before applying the lubricant. Therefore, the number of defects in Comparative Examples 1 to 3 is 30% smaller. Although filtration removes lubricant solids to some extent and reduces the number of defects, it is not as effective when isocyano groups are protected as in the present invention.
以上の実施例において説明したごとく本発明の磁気記録
媒体の潤滑膜形成方法により、欠陥の少ない、長期にわ
たって安定な製造プロセスが得られることがわかる。As explained in the above embodiments, it can be seen that the method for forming a lubricant film on a magnetic recording medium of the present invention provides a long-term stable manufacturing process with few defects.
次に、実施例１５〜２３により１本発明の方法で形成し
た潤滑膜が優れた摺動特性を有することを示す。Next, Examples 15 to 23 demonstrate that the lubricating film formed by the method of the present invention has excellent sliding properties.
実施例１５ 磁気記録媒体として、エポキシ、フェノール。Example 15 Epoxy and phenol as magnetic recording media.
およびポリビニルブチラール樹脂よりなるバインダ中に
磁性粉（γ−ＦｓｉＯｓ）を分散させて作製した５イン
チ径の塗布型磁気ディスクに１式（２）の含フッ素イソ
シアネート誘導体を所定の膜厚で塗布した。潤滑剤の塗
布は、フレオン溶液のがたちでスプレー塗布した後、磁
気ディスクを回転させながらガーゼテープで潤滑膜が所
定の膜厚になるまで過剰の潤滑剤を拭き取った。The fluorine-containing isocyanate derivative of Formula 1 (2) was coated to a predetermined thickness on a 5-inch diameter coated magnetic disk prepared by dispersing magnetic powder (γ-FsiOs) in a binder made of polyvinyl butyral resin. The lubricant was applied by spraying it in the form of a Freon solution, and then wiping off the excess lubricant with gauze tape while rotating the magnetic disk until the lubricant film reached a predetermined thickness.
なお、潤滑膜厚は、フーリエ変換型赤外分光器によって
測定した。Note that the lubricant film thickness was measured using a Fourier transform infrared spectrometer.
ついで、この磁気ディスクを２００℃で２時間加熱し、
潤滑膜とした。Next, this magnetic disk was heated at 200°C for 2 hours,
It was used as a lubricating film.
磁気ヘッドに対する摺動強度の測定は、上記の方法で作
製した磁気ディスクを、２０ｇの荷重を印加したサファ
イア摺動子（曲率半径５０■の球が発生するまでの回数
を測定することにより耐久性を評価した。The sliding strength of the magnetic head was measured by applying a load of 20 g to the magnetic disk produced by the method described above, and measuring the number of times a ball with a radius of curvature of 50 mm was generated. was evaluated.
実施例１６
実施例１７
実施例１８
比較例４
含フッ素イソシアネート誘導体のかわりに式（１）の含
フッ素インシアネートを用い、実施例１５と同様の方法
で行った。Example 16 Example 17 Example 18 Comparative Example 4 The same method as in Example 15 was carried out using the fluorine-containing incyanate of formula (1) instead of the fluorine-containing isocyanate derivative.
実施例１５〜１８および比較例４における試験結果を表
５に示す。The test results in Examples 15 to 18 and Comparative Example 4 are shown in Table 5.
表５
実施例１９
磁気記録媒体として、ＮｉＰをメツキしたＡＱ合金基板
上に、Ａｒガス雰囲気中の高周波スパッタリング法によ
り、膜厚０．２５ μｍのＣｒ、膜厚０．０６ ｐｍ
のＣｏ−Ｎｉ−Ｚｒ金属磁性膜、厚膜０．０５ μｍの
炭素保護膜を順次形成した磁気ディスク、潤滑剤として
式（２）の含フッ素イソシアネート誘導体を用い、実施
例１５と同様の方法で潤滑膜を形成した。Table 5 Example 19 As a magnetic recording medium, a Cr film with a thickness of 0.25 μm and a film with a thickness of 0.06 pm were deposited on an AQ alloy substrate plated with NiP by high-frequency sputtering in an Ar gas atmosphere.
A Co-Ni-Zr metal magnetic film, a magnetic disk on which a carbon protective film with a thickness of 0.05 μm was sequentially formed, and a fluorine-containing isocyanate derivative of formula (2) as a lubricant were used in the same manner as in Example 15. A lubricating film was formed.
なお、摺動強度の測定は、サファイア摺動子（曲率半径
５０■）を用い、荷重２０ｇ、スライディング速度２０
ｍ／ｓにて、上記摺動試験法と同様の方法で評価した。The sliding strength was measured using a sapphire slider (curvature radius of 50 mm) at a load of 20 g and a sliding speed of 20 mm.
m/s, and was evaluated using the same method as the above-mentioned sliding test method.
実施例２０
実施例２１
比較例５
含フッ素イソシアネート誘導体のかわりに式（１）の含
フッ素イソシアネートを用い、実施例１９と同様の方法
で行った。Example 20 Example 21 Comparative Example 5 The same method as in Example 19 was carried out using the fluorine-containing isocyanate of formula (1) instead of the fluorine-containing isocyanate derivative.
実施例１９〜２１、および比較例５における試験結果を
表６に示す。Table 6 shows the test results in Examples 19 to 21 and Comparative Example 5.
実施例２２
磁気記録媒体として、ポリイミドフィルム上に膜厚０．
２２ μｍのＣｏ−Ｃｒ金属磁性膜、膜厚０．０２ μ
ｍのボロン保護膜を順次蒸着により形成したフロッピー
ディスク、潤滑剤として式（２）の含フッ素イソシアネ
ート誘導体を用い、実施例１５と同様の方法で潤滑膜を
形成した。Example 22 As a magnetic recording medium, a film with a thickness of 0.5 mm was deposited on a polyimide film.
22 μm Co-Cr metal magnetic film, film thickness 0.02 μm
A lubricating film was formed in the same manner as in Example 15 using a floppy disk on which a boron protective film of m was formed by sequential vapor deposition, and a fluorine-containing isocyanate derivative of formula (2) as a lubricant.
なお、摺動強度の測定は、上記フロッピーディスクをガ
ラス板に接着し、サファイア摺動子（曲率半径５０■）
を用い、荷重２０ｇ、スライディング速度２ ｍ ／
ｓにて、上記摺動試験法と同様の方法で評価した。The sliding strength was measured by gluing the above floppy disk to a glass plate and using a sapphire slider (curvature radius of 50 cm).
using a load of 20g and a sliding speed of 2m/
s, and was evaluated using the same method as the above-mentioned sliding test method.
表 ６
実施例２３
比較例６
含フッ素イソシアネート誘導体のかわりに式（１）の含
フッ素イソシアネートを用い、実施例２２と同様の方法
で行った。Table 6 Example 23 Comparative Example 6 The same method as in Example 22 was carried out using the fluorine-containing isocyanate of formula (1) instead of the fluorine-containing isocyanate derivative.
実施例２２．２３および比較例６における試験結果を表
７に示す。The test results for Examples 22 and 23 and Comparative Example 6 are shown in Table 7.
表 ７
以上の実施例１５〜２３および比較例４〜６から次のこ
とがわかる。Table 7 The following can be seen from the above Examples 15 to 23 and Comparative Examples 4 to 6.
表５にみられるように、比較例４と膜厚もほぼ同じであ
る実施例１５〜１８を比較すると本発明による磁気ディ
スクは、いずれも摺動強度が、約３倍程度向上すること
が認められる。As shown in Table 5, when comparing Comparative Example 4 and Examples 15 to 18, which have almost the same film thickness, it was found that the sliding strength of the magnetic disks according to the present invention was improved by about three times. It will be done.
また、表６の実施例１９〜２１９表７の実施例２２．２
３に示すごとく１本発明は、金属磁性膜に対しても、塗
布型磁性膜と同様の優れた摺動強度が得られることが明
白である。In addition, Examples 19 to 219 in Table 6 and Example 22.2 in Table 7
As shown in No. 3, it is clear that the present invention can provide the same excellent sliding strength as a coated magnetic film even for a metal magnetic film.
以上、本発明の実施例において説明したごとく、本発明
による磁気記録媒体は、いずれの場合においても良好な
摺動強度を示し、磁気記録媒体として優れた耐久性なら
びに信頼性を有することがわかる。As described above in the examples of the present invention, it can be seen that the magnetic recording medium according to the present invention exhibits good sliding strength in all cases and has excellent durability and reliability as a magnetic recording medium.
以上詳細に説明したごとく１本発明の磁気記録媒体の潤
滑膜形成方法においては、含フッ素イソシアネートのイ
ソシアノ基の安定化により、加水分解性、自己重合性が
改善され、長期にわたって欠陥の少ない安定な製造プロ
セスが得られる。As explained in detail above, in the method for forming a lubricating film on a magnetic recording medium of the present invention, by stabilizing the isocyano group of the fluorine-containing isocyanate, hydrolyzability and self-polymerization are improved, and a stable film with few defects is produced over a long period of time. The manufacturing process is obtained.
また、本発明による潤滑膜形成方法によれば、優れた耐
久性ならびに信頼性を有する磁気記録媒体が得られる。Further, according to the method for forming a lubricating film according to the present invention, a magnetic recording medium having excellent durability and reliability can be obtained.
さらに、本発明は、塗布型磁気記録媒体、Ｃ。Furthermore, the present invention provides a coated magnetic recording medium, C.
Claims (1)
導体を情報記録媒体基板上に付着させた後、イソシアノ
基を再生し、重合させ、含フッ素イソシアネート重合膜
を形成することを特徴とする情報記録媒体の製造方法。 ２、上記イソシアノ基の再生および重合は、加熱によつ
て行う特許請求の範囲第１項記載の情報記録媒体の製造
方法。 ３、特許請求の範囲第１項記載の製造方法により製造し
たことを特徴とする情報記録媒体。 ４、特許請求の範囲第３項記載の情報記録媒体を用いた
ことを特徴とする情報記録装置。 ５、含フッ素イソシアネート化合物のイソシアノ基を保
護したことを特徴とする含フッ素イソシアネート誘導体
。[Claims] 1. A fluorine-containing isocyanate derivative with a protected isocyano group is deposited on an information recording medium substrate, and then the isocyano group is regenerated and polymerized to form a fluorine-containing isocyanate polymer film. A method for manufacturing an information recording medium. 2. The method for producing an information recording medium according to claim 1, wherein the regeneration and polymerization of the isocyano group are performed by heating. 3. An information recording medium manufactured by the manufacturing method according to claim 1. 4. An information recording device characterized by using the information recording medium according to claim 3. 5. A fluorine-containing isocyanate derivative characterized in that the isocyano group of the fluorine-containing isocyanate compound is protected.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2195688A JPH01199321A (en) | 1988-02-03 | 1988-02-03 | Production of information recording medium, information recording medium, information recording device and fluorine-contained isocyanate derivative |
| US07/304,086 US5008128A (en) | 1988-02-03 | 1989-01-31 | Process for producing information recording medium |
| DE3903264A DE3903264A1 (en) | 1988-02-03 | 1989-02-03 | INFORMATION RECORDING MATERIAL, METHOD FOR THE PRODUCTION THEREOF, INFORMATION RECORDING DEVICE AND FLUORINE-CONTAINING ISOCYANATE DERIVATIVES AND FLUORINE-BASED POLYMERS WITH ACYLAZIDO GROUPS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2195688A JPH01199321A (en) | 1988-02-03 | 1988-02-03 | Production of information recording medium, information recording medium, information recording device and fluorine-contained isocyanate derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01199321A true JPH01199321A (en) | 1989-08-10 |
Family
ID=12069512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2195688A Pending JPH01199321A (en) | 1988-02-03 | 1988-02-03 | Production of information recording medium, information recording medium, information recording device and fluorine-contained isocyanate derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01199321A (en) |
-
1988
- 1988-02-03 JP JP2195688A patent/JPH01199321A/en active Pending
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