JP6672146B2 - フルオロポリエーテル化合物、潤滑剤ならびに磁気ディスク - Google Patents
フルオロポリエーテル化合物、潤滑剤ならびに磁気ディスク Download PDFInfo
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- JP6672146B2 JP6672146B2 JP2016529575A JP2016529575A JP6672146B2 JP 6672146 B2 JP6672146 B2 JP 6672146B2 JP 2016529575 A JP2016529575 A JP 2016529575A JP 2016529575 A JP2016529575 A JP 2016529575A JP 6672146 B2 JP6672146 B2 JP 6672146B2
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- Prior art keywords
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- compound
- lubricant
- fluoropolyether
- magnetic disk
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- 150000001875 compounds Chemical class 0.000 title claims description 61
- 239000000314 lubricant Substances 0.000 title claims description 60
- 230000005291 magnetic effect Effects 0.000 title claims description 58
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 239000010410 layer Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 230000001050 lubricating effect Effects 0.000 claims description 10
- 150000001408 amides Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000011241 protective layer Substances 0.000 claims description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 4
- 101150065749 Churc1 gene Proteins 0.000 claims description 4
- 102100038239 Protein Churchill Human genes 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000002904 solvent Substances 0.000 description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
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- 229910052799 carbon Inorganic materials 0.000 description 10
- 230000001681 protective effect Effects 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- -1 phenoxy compound Chemical class 0.000 description 8
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- 229940125904 compound 1 Drugs 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
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- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 4
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- 125000003700 epoxy group Chemical group 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
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- 239000010702 perfluoropolyether Substances 0.000 description 2
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
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- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- AYMUQTNXKPEMLM-UHFFFAOYSA-N 1-bromononane Chemical compound CCCCCCCCCBr AYMUQTNXKPEMLM-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
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- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 1
- DZMDPHNGKBEVRE-UHFFFAOYSA-N 1-chloroheptane Chemical compound CCCCCCCCl DZMDPHNGKBEVRE-UHFFFAOYSA-N 0.000 description 1
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- RKAMCQVGHFRILV-UHFFFAOYSA-N 1-chlorononane Chemical compound CCCCCCCCCCl RKAMCQVGHFRILV-UHFFFAOYSA-N 0.000 description 1
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- SKIDNYUZJPMKFC-UHFFFAOYSA-N 1-iododecane Chemical compound CCCCCCCCCCI SKIDNYUZJPMKFC-UHFFFAOYSA-N 0.000 description 1
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- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 description 1
- VUOUSXLJIIFTIB-UHFFFAOYSA-N 2-[(4-butoxyphenoxy)methyl]oxirane Chemical compound C1=CC(OCCCC)=CC=C1OCC1OC1 VUOUSXLJIIFTIB-UHFFFAOYSA-N 0.000 description 1
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- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
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- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Description
1.式(1):
R1−CH2−R2−CH2−R3 (1)
[式中、R1は、炭素数1〜10のアルコキシ基である。R2は、−(CF2)pO(CF2O)x(CF2CF2O)y(CF2CF2CF2O)z(CF2CF2CF2CF2O)w(CF2)p−である。x及びyは、それぞれ0〜30の実数である。zは0〜30の実数である。wは0〜20の実数である。pは1〜3の整数である。
R3は、−OCH2CH(OH)CH2OH、−OCH2CH(OH)CH2OCH2CH(OH)CH2OH、−O(CH2)mOH、または−OCH2(OH)CHCH2−OC6H4−R4である。mは2〜8の整数である。R4は水素、炭素数1〜4のアルコキシ基、アミノ基、又はアミド残基である。]
で表されるフルオロポリエーテル化合物。
2.前記式(1)で表されるフルオロポリエーテル化合物を含有する潤滑剤。
3.さらに磁気ディスク用潤滑剤を含有する上記項2に記載の潤滑剤。
4.上記項2に記載の潤滑剤と前記磁気ディスク用潤滑剤とを、重量比で1:99〜50:50の割合で含有する、上記項3に記載の潤滑剤。
5.支持体上に少なくとも記録層及び保護層を形成し、その表面に潤滑層を有する磁気ディスクにおいて、該潤滑層が上記項3又は4に記載の潤滑剤を含有する磁気ディスク。
R1−CH2−R2―CH2−R3 (1)
[式中、R1は、炭素数1〜10のアルコキシ基である。R2は、−(CF2)pO(CF2O)x(CF2CF2O)y(CF2CF2CF2O)z(CF2CF2CF2CF2O)w(CF2)p−である。x及びyは、それぞれ0〜30の実数である。zは0〜30の実数である。wは0〜20の実数である。pは1〜3の整数である。
R3は、−OCH2CH(OH)CH2OH、−OCH2CH(OH)CH2OCH2CH(OH)CH2OH、−O(CH2)mOH、または−OCH2(OH)CHCH2−OC6H4−R4である。mは2〜8の整数である。R4は水素、炭素数1〜4のアルコキシ基、アミノ基、又はアミド残基である。]
で表されるものである。
CH3CH2CH2OCH2CF2O(CF2O)x(CF2CF2O)yCF2CH2OCH2CH(OH)CH2OH(化合物1)の合成
アルゴン雰囲気下、t−ブチルアルコール(40g)、HO−CH2CF2O(CF2O)x(CF2CF2O)yCF2CH2−OHで表されるフルオロポリエーテル(数平均分子量1720、分子量分布1.20)100g、カリウム t−ブトキシド(0.7g)、及びグリシドール(5g)の混合物を70℃で14時間撹拌した。その後、水洗及び脱水し、シリカゲルカラムクロマトグラフィーにより精製し、一方の末端に1つの水酸基を有し、もう一方の末端に2つの水酸基を有する、パーフルオロポリエーテル(平均分子量1842)を95g得た。この化合物(95g)をt−ブチルアルコール(43g)に溶解させ、カリウム t−ブトキシド(6g)、1−ブロモプロパン(15g)を加えて70℃で14時間撹拌した。その後、水洗及び脱水した後、蒸留により精製し、化合物1を65g得た。
δ=−52.1ppm、−53.7ppm、−55.4ppm
〔16F、CH3CH2CH2OCH2CF2O(CF 2 O)x(CF2CF2O)yCF2CH2OCH2CH(OH)CH2OH〕、
δ=−89.1ppm、−90.7ppm
〔32F、CH3CH2CH2OCH2CF2O(CF2O)x(CF 2 CF 2 O)yCF2CH2OCH2CH(OH)CH2OH〕、
δ=−78.6ppm、−80.6ppm
〔2F、CH3CH2CH2OCH2CF2O(CF2O)x(CF2CF2O)yCF 2 CH2OCH2CH(OH)CH2OH〕、
δ=−78.0ppm、−80.1ppm
〔2F、CH3CH2CH2OCH2CF 2 O(CF2O)x(CF2CF2O)yCF2CH2OCH2CH(OH)CH2OH〕、
x=8.9、y=8.7
δ=3.2〜3.8ppm
〔11H、CH3CH2CH2OCH 2 −CF2O(CF2O)x(CF2CF2O)yCF2CH 2 −O−CH 2 CH(OH)CH 2 OH〕
δ=0.5〜1.2ppm
〔7H、CH 3 CH 2 CH 2 OCH2−CF2O(CF2O)x(CF2CF2O)yCF2CH 2 −O−CH2CH(OH)CH2OH〕
CH3CH2CH2OCH2CF2CF2O(CF2CF2CF2O)zCF2CF2CH2OCH2CH(OH)CH2OH(化合物2)の合成
実施例1において用いたHO−CH2CF2O(CF2O)x(CF2CF2O)yCF2−CH2−OHで表されるフルオロポリエーテルの代わりに、HO−CH2CF2CF2O(CF2CF2CF2O)zCF2CF2−CH2−OHで表されるフルオロポリエーテルを用いた以外は実施例1と同様にして、化合物2を60g得た。
δ=−129.7ppm
〔18F、−OCF2CF 2 CF2O−〕、
δ=−83.7
〔36F、−OCF 2 CF2CF 2 O−〕、
δ=−124.2ppm
〔2F、CH3CH2CH2OCH2CF2CF2O(CF2CF2CF2O)zCF 2 CF2CH2OCH2CH(OH)CH2OH〕、
δ=−122.4ppm
〔2F、CH3CH2CH2OCH2CF2CF 2 O(CF2CF2CF2O)zCF2CF2CH2OCH2CH(OH)CH2OH〕、
δ=−86.5ppm
〔4F、CH3CH2CH2OCH2CF 2 CF2O(CF2CF2CF2O)zCF2CF 2 CH2OCH2CH(OH)CH2OH〕
z=9.3
δ=3.2〜3.8ppm
〔11H、CH3CH2CH2OCH 2 −CF2CF2O(CF2CF2CF2O)zCF2CF2CH 2 −O−CH 2 CH(OH)CH 2 OH〕
δ=0.5〜1.2ppm
〔7H、CH 3 CH 2 CH 2 OCH2−CF2CF2O(CF2CF2CF2O)zCF2CF2CH 2 −O−CH2CH(OH)CH2OH〕
CH3CH2CH2OCH2CF2CF2CF2O(CF2CF2CF2CF2O)wCF2CF2CF2CH2OCH2CH(OH)CH2OH(化合物3)の合成
実施例1において用いたHO−CH2CF2O(CF2O)x(CF2CF2O)yCF2−CH2−OHで表されるフルオロポリエーテルの代わりに、HO−CH2CF2CF2CF2O(CF2CF2CF2CF2O)wCF2CF2CF2−CH2−OHで表されるフルオロポリエーテルを用いた以外は実施例1と同様にして、化合物3を59g得た。
δ=−83.7ppm
〔24F、CH3CH2CH2OCH2CF2CF2CF 2 O(CF 2 CF2CF2CF 2 O)wCF 2 CF2CF2CH2OCH2CH(OH)CH2OH〕、
δ=−123.3ppm
〔2F、CH3CH2CH2OCH2CF2CF2CF2O(CF2CF2CF2CF2O)wCF2CF2CF 2 CH2OCH2CH(OH)CH2OH〕、
δ=−121.5ppm
〔2F、CH3CH2CH2OCH2CF 2 CF2CF2O(CF2CF2CF2CF2O)wCF2CF2CF2CH2OCH2CH(OH)CH2OH〕、
δ=−125.8ppm
〔12F、−OCF2CF 2 CF 2 CF2O−〕、
δ=−127.6ppm
〔4F、CH3CH2CH2OCH2CF2CF 2 CF2O(CF2CF2CF2CF2O)wCF2CF 2 CF2CH2OCH2CH(OH)CH2OH〕
w=5.2
δ=3.2〜3.8ppm
〔11H、CH3CH2CH2OCH 2 CF2CF2CF2O(CF2CF2CF2CF2O)wCF2CF2CF2CH 2 OCH 2 CH(OH)CH 2 OH〕
δ=0.5〜1.2ppm
〔7H、CH 3 CH 2 CH 2 OCH2CF2CF2CF2O(CF2CF2CF2CF2O)wCF2CF2CF2CH2OCH2CH(OH)CH2OH〕
化合物4として、前記引用文献2(国際公開第2009/066784号)の段落[0004]に記載されている式(5)の化合物(HOCH2CH(OH)CH2OCH2CF2CF2O(CF2CF2CF2O)zCF2CF2CH2OCH2CH(OH)CH2OH)を使用した。化合物4は、以下の製造方法に従って製造されたものであり、分子の両末端にそれぞれ水酸基を2個ずつ有している。
δ=−129.7ppm
〔26F,−OCF2CF 2 CF2O−〕,
δ=−83.7
〔52F,−OCF 2 CF2CF 2 O−〕,
δ=−124.2ppm
〔4F,−OCF 2 CF2CH2OCH2CH(OH)CH2OH〕,
δ=−86.5ppm
〔4F,−OCF2CF 2 CH2OCH2CH(OH)CH2OH〕
z=13.0
δ=3.2〜3.8ppm
〔18H,HO−CH 2 CH(OH)CH 2 O−CH 2 CF2CF2O(CF2CF2CF2O)zCF2CF2CH 2 −O−CH 2 CH(OH)CH 2 OH〕
潤滑剤(化合物1〜4)に、それぞれ20重量%のAl2O3を入れ、強く振とうしたのち超音波でさらに良く混合することにより、耐分解性評価用の試料を調製した。耐分解性の評価は、熱分析装置(TG/TDA)を用いて、250℃で100分間加熱した後の潤滑剤の重量減少率を測定することにより行った。試料は20mg、測定は窒素雰囲気下で行った。得られた結果を表1に示す。
実施例1で合成した化合物1を、それぞれDuPont製Vertrel−XFに溶解した。直径2.5インチの磁気ディスクをこの溶液に1分間浸漬し、速度2mm/sで引き上げた。その後潤滑剤を塗布したディスクを、波長185nm及び254nmの紫外光を発光する低圧水銀ランプを取り付けた紫外線照射装置の内部に10〜20秒間挿入した。この際、オゾンの形成を防ぐため、紫外線照射装置の内部は予め窒素で置換した。この後、Fourier Transform Infrared Spectorometer(FT−IR)でディスク上の化合物の平均膜厚を測定した。この膜厚をfÅとする。次に、このディスクをVertrel−XF中に10分間浸漬し、速度10mm/sで引き上げた後、室温下で静置して溶媒を揮発させた。この後、ディスク上に残った化合物の平均膜厚をFT−IRで測定した。この膜厚をbÅとする。ディスクとの吸着性の強弱を示す指標として、一般に用いられているボンド率を採用した。ボンド率は、下記式で表される。
ボンド率(%)=100×b/f
化合物4、及び化合物1:化合物4=15wt%:85wt%の混合溶液をDuPont製Vertrel−XFに溶解した。この溶液中の潤滑剤の濃度は0.05重量%であった。直径2.5インチの磁気ディスクをこの溶液に1分間浸漬し、速度2mm/sで引き上げた。この後、磁気ヘッドを装着し、この作成した磁気ディスクを5400rpmで高速回転させた。その後、磁気ヘッドへ付着した潤滑剤の量を測定した。
2 記録層
3 保護層
4 潤滑層
Claims (5)
- 式(1):
R1−CH2−R2−CH2−R3 (1)
[式中、R1は、炭素数1〜10のアルコキシ基である。R2は、−(CF2)pO(CF2O)x(CF2CF2O)y(CF2CF2CF2O)z(CF2CF2CF2CF2O)w(CF2)p−である。x及びyは、それぞれ0〜30の実数である。zは0〜30の実数である。wは0〜20の実数である。pは1〜3の整数である。
R3は、−OCH2CH(OH)CH2OH、−OCH2CH(OH)CH2OCH2CH(OH)CH2OH、−O(CH2)mOH、または−OCH2(OH)CHCH2−OC6H4−R4である。mは2〜8の整数である。R4は水素、炭素数1〜4のアルコキシ基、アミノ基、又はアミド残基である。]
で表されるフルオロポリエーテル化合物。 - 式(1):
R1−CH2−R2−CH2−R3 (1)
[式中、R1は、炭素数1〜10のアルコキシ基である。R2は、−(CF2)pO(CF2O)x(CF2CF2O)y(CF2CF2CF2O)z(CF2CF2CF2CF2O)w(CF2)p−である。x及びyは、それぞれ0〜30の実数である。zは0〜30の実数である。wは0〜20の実数である。pは1〜3の整数である。
R3は、−OCH2CH(OH)CH2OH、−OCH2CH(OH)CH2OCH2CH(OH)CH2OH、−O(CH2)mOH、または−OCH2(OH)CHCH2−OC6H4−R4である。mは2〜8の整数である。R4は水素、炭素数1〜4のアルコキシ基、アミノ基、又はアミド残基である。]
で表されるフルオロポリエーテル化合物を含有する潤滑剤。 - さらに磁気ディスク用潤滑剤を含有する請求項2に記載の潤滑剤。
- 請求項2に記載の潤滑剤と前記磁気ディスク用潤滑剤とを、重量比で1:99〜50:50の割合で含有する、請求項3に記載の潤滑剤。
- 支持体上に少なくとも記録層及び保護層を形成し、その表面に潤滑層を有する磁気ディスクにおいて、該潤滑層が請求項3又は4に記載の潤滑剤を含有する磁気ディスク。
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US11308985B2 (en) | 2018-01-29 | 2022-04-19 | Seagate Technology Llc | Fluoropolyether compound and lubricant |
US11767483B2 (en) | 2018-09-12 | 2023-09-26 | Resonac Corporation | Fluorine-containing ether compound, lubricant for magnetic recording medium, and magnetic recording medium |
US11651789B2 (en) | 2019-01-24 | 2023-05-16 | Moresco Corporation | Fluoropolyether compound, lubricant using same and usage thereof |
US11820953B2 (en) | 2019-03-12 | 2023-11-21 | Resonac Corporation | Fluorine-containing ether compound, lubricant for magnetic recording medium and magnetic recording medium |
JP7447903B2 (ja) | 2019-07-31 | 2024-03-12 | 株式会社レゾナック | 含フッ素エーテル化合物、磁気記録媒体用潤滑剤および磁気記録媒体 |
US11879109B2 (en) | 2019-09-18 | 2024-01-23 | Resonac Corporation | Fluorine-containing ether compound, lubricant for magnetic recording medium, and magnetic recording medium |
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JP4828114B2 (ja) | 2004-11-15 | 2011-11-30 | 富士通株式会社 | 組成物を含む潤滑剤、磁気記録媒体、ヘッドスライダおよび磁気記録装置 |
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