Fluorine-containing ether compound, lubricant for magnetic recording medium, and magnetic recording medium
The present invention provides a fluorine-containing ether compound that can form a lubricating layer which has excellent wear resistance even if the thickness is thin and in which a decrease in film thickness due to spin-off is less likely to occur. The fluorine-containing ether compound is represented by the following formula. R 1 —R 2 —O—CH 2 —R 3 —CH 2 —O—R 4 —R 5 (R 3 is a perfluoropolyether chain. R 1 and R 5 are either an alkyl group which may have a substituent or a hydrocarbon group having a double bond or triple bond. R 2 and R 4 are each a divalent linking group containing one or more heteroatoms, and have one or more polar groups, and the terminal end on the side bonded to R 1 and R 5 is a heteroatom. At least one of R 2 and R 4 contains one or more secondary amine structures. At least one of R 1 —R 2 — and —R 4 —R 5 contains one or more cyano groups).
1. A fluorine-containing ether compound represented by Formula (1) shown below:
(in Formula (1), R 3 is a perfluoropolyether chain; R 1 and R 5 are each independently a terminal group composed of either an alkyl group which may have a substituent or a hydrocarbon group having a double bond or triple bond; R 2 and R 4 are each a divalent linking group containing one or more heteroatoms and have one or more polar groups, and a terminal end thereof on the side bonded to R 1 and R 5 is a heteroatom; at least one of R 2 and R 4 contains one or more secondary amine structures; and at least one of R 1 -R 2 — and —R 4 -R 5 contains one or more cyano groups).
2. The fluorine-containing ether compound according to claim 1 ,
wherein the polar groups of R 2 and R 4 are any one selected from a secondary amine structure, a hydroxyl group and a cyano group.
3. The fluorine-containing ether compound according to claim 1 ,
wherein, in Formula (1), —R 2 —O— is represented by Formula (2) shown below, and —O—R 4 — is represented by Formula (3) shown below:
(in Formula (2), [A] is represented by Formula (4-1) shown below, and [B] is represented by Formula (4-2) shown below; the order of [A] and [B] in Formula (2) may be interchanged; a is an integer of 0 to 3, d is an integer of 0 to 3, at least one of a and d is 1 or more; and a terminal —CH 2 — located on the side opposite to X in Formula (4-1) or a terminal —CH 2 — located on the side opposite to X in (4-2) is bonded to —O— in Formula (2))
(in Formula (3), [C] is represented by Formula (5-1) shown below, and [D] is represented by Formula (5-2) shown below; the order of [C] and [D] in Formula (3) may be interchanged; g is an integer of 0 to 3, j is an integer of 0 to 3, and at least one of g and j is 1 or more; and a terminal —CH 2 — located on the side opposite to X in Formula (5-1) or a terminal —CH 2 — located on the side opposite to X in (5-2) is bonded to —O— in Formula (3))
(in Formula (4-1), b and c are each an integer of 0 to 4; in Formula (4-2), e and f are each an integer of 0 to 4; in Formula (5-1), h and i are each an integer of 0 to 4; in Formula (5-2), k and l are each an integer of 0 to 4; in Formulae (4-1), (4-2), (5-1), and (5-2), X is O or NH; and
one or more of X's in Formulae (4-1), (4-2), (5-1), and (5-2) are NH).
4. The fluorine-containing ether compound according to claim 1 ,
wherein the number of secondary amine structures contained in a molecule thereof is 2 or more.
5. The fluorine-containing ether compound according to claim 1 ,
wherein the number of hydroxyl groups contained in a molecule thereof is 3 or less.
6. The fluorine-containing ether compound according to claim 1 ,
wherein the number of cyano groups contained in a molecule thereof is 3 or less.
7. The fluorine-containing ether compound according to claim 1 ,
wherein a total number of secondary amine structures, hydroxyl groups and cyano groups contained in the molecule is 8 or less.
8. The fluorine-containing ether compound according to claim 1 ,
wherein the number of secondary amine structures contained in a molecule thereof is 2 or more, the number of hydroxyl groups is 3 or less, the number of cyano groups is 3 or less, and a total number of secondary amine structures, hydroxyl groups and cyano groups is 8 or less.
9. The fluorine-containing ether compound according to claim 1 ,
wherein —R 2 —O— in Formula (1) is any of Formulae (11-1) to (11-12) shown below:
10. The fluorine-containing ether compound according to claim 1 ,
wherein the alkyl group which may have a substituent is an alkyl group having a hydroxyl group or cyano group.
11. The fluorine-containing ether compound according to claim 1 ,
wherein the hydrocarbon group having a double bond or triple bond is any of a group containing an aromatic hydrocarbon, a group containing an aromatic heterocycle, an alkenyl group, and an alkynyl group.
12. The fluorine-containing ether compound according to claim 1 ,
wherein R 3 in Formula (1) is any of Formulae (6) to (10) shown below:
(in Formula (6), m and n indicate an average degree of polymerization, and each represent 0.1 to 30)
(in Formula (7), w indicates an average degree of polymerization, and is 0.1 to 30)
(in Formula (8), x indicates an average degree of polymerization, and is 0.1 to 30)
(in Formula (9), y indicates an average degree of polymerization, and is 0.1 to 30)
(in Formula (10), z indicates an average degree of polymerization, and is 0.1 to 30).
13. The fluorine-containing ether compound according to claim 1 ,
wherein the compound represented by Formula (1) is any one of compounds represented by Formulae (A), (J), (P), (Q) and (U) shown below:
(in Formula (A), ma and na indicate an average degree of polymerization, ma is 1 to 30, and na is 0.1 to 30)
(in Formula (J), mj and nj indicate an average degree of polymerization, mj is 1 to 30, and nj is 0.1 to 30)
(in Formula (P), mp and np indicate an average degree of polymerization, mp is 1 to 30, and np is 0.1 to 30)
(in Formula (Q), mq and nq indicate an average degree of polymerization, mq is 1 to 30, and nq is 0.1 to 30)
(in Formula (U), mu and nu indicate an average degree of polymerization, mu is 1 to 30, and nu is 0.1 to 30).
14. The fluorine-containing ether compound according to claim 1 ,
wherein a number-average molecular weight thereof is in a range of 500 to 10,000.
15. A lubricant for a magnetic recording medium, which contains the fluorine-containing ether compound according to claim 1 .
16. A magnetic recording medium in which at least a magnetic layer, a protective layer and a lubricating layer are sequentially provided on a substrate,
wherein the lubricating layer contains the fluorine-containing ether compound according to claim 1 .
17. The magnetic recording medium according to claim 16 ,
wherein the lubricating layer has an average film thickness of 0.5 nm to 2.0 nm.