IP Library Granted Patent US 12,100,434
Granted Patent B2
US 12,100,434 · App. 17/797,177 · Granted Sep 24, 2024

Fluorine-containing ether compound, lubricant for magnetic recording medium, and magnetic recording medium

Inventors: Daisuke Yagyu (Ichihara, JP); Tsuyoshi Kato (Ichihara, JP); Ayano Asano (Ichihara, JP); Natsumi Shibata (Ichihara, JP); Naoya Fukumoto (Ichihara, JP)
Assignee: Resonac Corporation
G11B5/7257C07D303/28C07D309/12C07D405/12C07D407/12C07D409/12C10M105/54C10M105/70C10M105/72C10M2211/0425C10M2215/305C10M2219/102C10N2020/04C10N2040/18
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Quick Facts
Patent No.
US 12,100,434
App. No.
17/797,177
Granted
Sep 24, 2024
Kind
B2
Abstract

A fluorine-containing ether compound represented by a formula (1) shown below. R 1 —(O(CH 2 ) a ) b -[A]-[B]—O—CH 2 —R 2 —CH 2 —R 3   (1) (In the formula (1), R 1 is an alkyl group which may have a substituent, or an organic group having at least one double bond or triple bond. Further, a represents an integer of 2 to 4, and b is 0 or 1. [A] is represented by a formula (2): —(OCH 2 CH(OH)CH 2 ) c — (wherein c is 1 or 2). [B] is represented by a formula (3): —(O(CH 2 ) e CH(OH)CH 2 ) d — (wherein d is 0 or 1, and e represents an integer of 2 to 4). However, the sum of c in the formula (2) and d in the formula (3) is 2. R 2 is a perfluoropolyether chain. R 3 is represented by a formula (4): —(OCH 2 CH(OH)CH 2 ) 2 —O—CH 2 (CH 2 ) f OH (wherein f represents an integer of 2 to 5).

Claims (34)

1. A fluorine-containing ether compound represented by a formula (1) shown below:

R 1 —(O(CH 2 ) a ) b -[A]-[B]—O—CH 2 —R 2 —CH 2 —R 3   (1)

wherein in the formula (1), R 1 is an alkyl group which may have a substituent, or an organic group having at least one double bond or triple bond, a represents an integer of 2 to 4, b represents 0 or 1, [A] is represented by a formula (2) shown below, wherein c in the formula (2) is 1 or 2, [B] is represented by a formula (3) shown below, wherein d in the formula (3) is 0 or 1, and e represents an integer of 2 to 4, provided that a sum of c in the formula (2) and d in the formula (3) is 2, R 2 is a perfluoropolyether chain, R 3 is represented by a formula (4) shown below, and f in the formula (4) represents an integer of 2 to 5.

2. The fluorine-containing ether compound according to claim 1 , wherein the fluorine-containing ether compound has a number average molecular weight within a range from 1,000 to 2,300.

3. The fluorine-containing ether compound according to claim 1 , wherein R 1 in the formula (1) is an alkyl group of 1 to 6 carbon atoms.

4. The fluorine-containing ether compound according to claim 1 ,

wherein R 1 in the formula (1) is an alkyl group of 1 to 6 carbon atoms that has a substituent, and

the substituent is a fluoro group or a cyano group.

5. The fluorine-containing ether compound according to claim 1 , wherein R 1 in the formula (1) is any one of an organic group of 6 to 12 carbon atoms containing an aromatic hydrocarbon, an organic group of 3 to 10 carbon atoms containing an aromatic heterocycle, an alkenyl group of 2 to 8 carbon atoms, and an alkynyl group of 3 to 8 carbon atoms.

6. The fluorine-containing ether compound according to claim 1 , wherein R 1 in the formula (1) is one group selected from a group consisting of a methyl group, ethyl group, n-propyl group, isopropyl group, 2,2,2-trifluoroethyl group, 2,2,3,3,3-pentafluoropropyl group, 2,2,2,2,2,2-hexafluoroisopropyl group, 2-cyanoethyl group, 3-cyanopropyl group, 4-cyanobutyl group, phenyl group, methoxyphenyl group, cyanophenyl group, phenethyl group, thienylethyl group, N-methylpyrazolylmethyl group, allyl group, 3-butenyl group, 4-pentenyl group, propargyl group, 3-butynyl group, and 4-pentynyl group.

7. The fluorine-containing ether compound according to claim 1 ,

wherein R 2 in the formula (1) is represented by one of formula (5) to (8) shown below:

—CF 2 O—(CF 2 CF 2 O) g —(CF 2 O) h —CF 2 —  (5)

in the formula (5), g and h indicate average polymerization degrees, wherein g represents a number from 3 to 8, and h represents a number from 3 to 8,

—CF 2 O—(CF 2 CF 2 O) i —CF 2 —  (6)

in the formula (6), i indicates an average polymerization degree, and represents a number from 5 to 13,

—CF 2 CF 2 O—(CF 2 CF 2 CF 2 O) j —CF 2 CF 2 —  (7)

in the formula (7), j indicates an average polymerization degree, and represents a number from 3 to 8, and

—CF(CF 3 )—(OCF(CF 3 )CF 2 ) k —OCF(CF 3 )—  (8)

in the formula (8), k indicates an average polymerization degree, and represents a number from 3 to 8.

8. The fluorine-containing ether compound according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by one of formulas (A1) to (A3), (B1) to (B3), (L1) and (M1) shown below:

in the formula (A1), ma1 and na1 indicate average polymerization degrees, wherein ma1 represents a number from 3 to 8, and na1 represents a number from 3 to 8,

in the formula (A2), na2 indicates an average polymerization degree, and represents a number from 5 to 13,

in the formula (A3), na3 indicates an average polymerization degree, and represents a number from 3 to 8,

in the formula (B1), mb1 and nb1 indicate average polymerization degrees, wherein mb1 represents a number from 3 to 8, and nb1 represents a number from 3 to 8,

in the formula (B2), nb2 indicates an average polymerization degree, and represents a number from 5 to 13,

in the formula (B3), nb3 indicates an average polymerization degree, and represents a number from 3 to 8,

in the formula (L1), ml1 and nl1 indicate average polymerization degrees, wherein ml1 represents a number from 3 to 8, and nl1 represents a number from 3 to 8, and

in the formula (M1), mm1 and nm1 indicate average polymerization degrees, wherein mm1 represents a number from 3 to 8, and nm1 represents a number from 3 to 8.

9. A lubricant for a magnetic recording medium, the lubricant comprising the fluorine-containing ether compound according to claim 1 .

10. A magnetic recording medium comprising:

at least a magnetic layer, a protective layer and a lubricant layer provided sequentially on a substrate,

wherein the lubricant layer contains the fluorine-containing ether compound according to claim 1 .

11. The magnetic recording medium according to claim 10 , wherein an average thickness of the lubricant layer is within a range from 0.5 nm to 2.0 nm.

Assignments (3)
CHANGE OF ADDRESS Recorded Feb 9, 2024
From: RESONAC CORPORATION
To: RESONAC CORPORATION
Reel/Frame 066547/0677 →
CHANGE OF NAME Recorded Jun 23, 2023
From: SHOWA DENKO K.K.
To: RESONAC CORPORATION
Reel/Frame 064082/0513 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 3, 2022
From: YAGYU, DAISUKE; KATO, TSUYOSHI; ASANO, AYANO; SHIBATA, NATSUMI; FUKUMOTO, NAOYA
To: SHOWA DENKO K.K.
Reel/Frame 061058/0269 →
Priority Claims (1)
JP JP2020-020180 · Feb 7, 2020 · national
Continuity (1)
Related Publication 20230115042A1 · Apr 13, 2023