IP Library Granted Patent US 11,905,365
Granted Patent B2
US 11,905,365 · App. 17/788,075 · Granted Feb 20, 2024

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

Inventor: Masaki Nanko (Ichihara, JP)
Assignee: Resonac Corporation
C08G65/007C08G65/3312C08G65/33306C10M107/38G11B5/7257C10M2213/043C10N2040/18C10N2050/025C10N2070/00
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Quick Facts
Patent No.
US 11,905,365
App. No.
17/788,075
Granted
Feb 20, 2024
Kind
B2
Abstract

The present invention provides a fluorine-containing ether compound represented by the following formula: R 1 —R 2 —CH 2 —R 3 —CH 2 —R 4 —R 5 (in the formula, R 3 represents a perfluoropolyether chain; R 1 and R 5 each independently represent any of an alkyl group which may have a substituent, an organic group having a double bond or a triple bond, and a hydrogen atom; —R 2 —CH 2 —R 3 is represented by -[A]-[B]—O—CH 2 —R 3 ; R 3 —CH 2 —R 4 — is represented by R 3 —CH 2 —O—[C]-[D]-; [A] is represented by Formula (4), [B] is represented by Formula (5), [C] is represented by Formula (6), and [D] is represented by Formula (7)):

Claims (45)

1. A fluorine-containing ether compound represented by the following Formula (1):

R 1 —R 2 —CH 2 —R 3 —CH 2 —R 4 —R 5   (1)

(in Formula (1), R 3 represents a perfluoropolyether chain; R 1 represents a terminal group bonded to R 2 ; R 5 represents a terminal group bonded to R 4 ; R 1 and R 5 each independently represent any of an alkyl group which may have a substituent, an organic group having a double bond or a triple bond, and a hydrogen atom; —R 2 —CH 2 —R 3 is represented by the following Formula (2); and R 3 —CH 2 —R 4 — is represented by the following Formula (3); and a total of one or more secondary amine —NH— is contained in R 2 and R 4 ):

-[A]-[B]—O—CH 2 —R 3   (2)

R 3 —CH 2 —O—[C]-[D]-  (3)

(in Formula (2), [A] is represented by the following Formula (4), and [B] is represented by the following Formula (5); and in Formula (2), [A] and [B] may be interchanged), and

(in Formula (3), [C] is represented by the following Formula (6), and [D] is represented by the following Formula (7); and in Formula (3), [C] and [D] may be interchanged):

(a in Formula (4) and b in Formula (5) represent an integer of 0 to 2; c in Formula (5) represents an integer of 2 to 5; din Formula (6) and e in Formula (7) represent an integer of 0 to 2; fin Formula (7) represents an integer of 2 to 5; at least one of b in Formula (5) and din Formula (6) represents 1 or more; X represents any of O, NH, and CH 2 ; one or more of X's in Formulae (4) to (7) represent NH; and when X bonded to R 1 or R 5 represents NH, R 1 or R 5 represents either an alkyl group which may have a substituent or an organic group having a double bond or a triple bond).

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

wherein the number of secondary amine structures contained in the molecule is 2 or more.

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

wherein the number of hydroxy groups contained in the molecule is 4 or less.

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

wherein a total number of secondary amine structures and hydroxy groups contained in the molecule is 7 or less.

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

wherein, in the molecule thereof, the number of secondary amine structures is 2 or more, the number of hydroxy groups is 4 or less, and a total number of secondary amine structures and hydroxy groups is 7 or less.

6. The fluorine-containing ether compound according to claim 1 , wherein, in Formula (1), R 2 represents any of the following Formulae (11-1) to (11-5):

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

wherein the alkyl group which may have a substituent is an alkyl group having a hydroxy group and having 1 to 6 carbon atoms.

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

wherein the organic group having a double bond or a triple bond is any one of an aromatic hydrocarbon-containing group, an aromatic heterocycle-containing group, an alkenyl group, and an alkynyl group.

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

wherein, in Formula (1), R 3 represents any of the following Formulae (8) to (10):

—CF 2 O—(CF 2 CF 2 O) m —(CF 2 O) n —CF 2 —  (8)

(in Formula (8), m and n indicate an average degree of polymerization, and each represents 0 to 30; where, m or n is 0.1 or more),

—CF(CF 3 )—(OCF(CF 3 )CF 2 ) y —OCF(CF 3 )—  (9)

(in Formula (9), y indicates an average degree of polymerization, and represents 0.1 to 30), and

—CF 2 CF 2 O—(CF 2 CF 2 CF 2 O) z —CF 2 CF 2 —  (10)

(in Formula (10), z indicates an average degree of polymerization, and represents 0.1 to 30).

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

wherein a sum of a in Formula (4) and b in Formula (5), and a sum of d in Formula (6) and e in Formula (7) are each 1 or more.

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

wherein the compound represented by Formula (1) is any of compounds represented by the following Formulae (K) to (M), (S), and (T):

(in Formula (K), mk and nk indicate an average degree of polymerization, mk represents 1 to 30, and nk represents 0 to 30),

(in Formula (L), ml and nl indicate an average degree of polymerization, ml represents 1 to 30, and nl represents 0 to 30),

(in Formula (M), mm and nm indicate an average degree of polymerization, mm represents 1 to 30, and nm represents 0 to 30),

(in Formula (S), ms and ns indicate an average degree of polymerization, ms represents 1 to 30, and ns represents 0 to 30), and

(in Formula (T), mt and nt indicate an average degree of polymerization, mt represents 1 to 30, and nt represents 0 to 30).

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

wherein the number-average molecular weight thereof is in a range of 500 to 10,000.

13. A lubricant for a magnetic recording medium, which contains the fluorine-containing ether compound according to claim 1 .

14. A magnetic recording medium having at least a magnetic layer, a protective layer, and a lubricating layer sequentially provided on a substrate,

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

15. The magnetic recording medium according to claim 14 ,

wherein the average film thickness of the lubricating layer is 0.5 nm to 2.0 nm.

Assignments (4)
CHANGE OF ADDRESS Recorded Feb 9, 2024
From: RESONAC CORPORATION
To: RESONAC CORPORATION
Reel/Frame 066547/0677 →
CHANGE OF ADDRESS Recorded Nov 14, 2023
From: RESONAC CORPORATION
To: RESONAC CORPORATION
Reel/Frame 065564/0523 →
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 Jun 22, 2022
From: NANKO, MASAKI
To: SHOWA DENKO K.K.
Reel/Frame 060276/0805 →