Fluorine-containing ether compound, lubricant for magnetic recording medium, and magnetic recording medium
A fluorine-containing ether compound represented by the following formula. R 1 —CH 2 —R 2 [—CH 2 —R 3 —CH 2 —R 2 ] x —CH 2 —R 4 (x is 1 or 2, R 2 is a perfluoropolyether chain, R 3 is represented by Formula (2), and R 1 and R 4 are each a terminal group having 1 to 50 carbon atoms, which has 1 to 4 polar groups, and in Formula (2), a1 and a2 are each 0 to 5, b is 0 or 1, and Y is an acyclic divalent saturated hydrocarbon group having 2 to 8 carbon atoms)
1 . A fluorine-containing ether compound represented by Formula (1),
R 1 —CH 2 —R 2 [—CH 2 —R 3 —CH 2 —R 2 ] x —CH 2 —R 4 (1)
(in Formula (1), x represents 1 or 2; R 2 is a perfluoropolyether chain; (x+1) pieces of R 2 's may be partially or entirely the same as or different from each other; R 3 is a divalent linking group represented by Formula (2); in a case where x is 2, two R 3 's may be the same as or different from each other; R 1 and R 4 are each a terminal group having 1 to 50 carbon atoms, which has 1 to 4 polar groups; and R 1 and R 4 may be the same as or different from each other)
(in Formula (2), a1 and a2 each represent an integer of 0 to 5; a1 and a2 may be the same as or different from each other, and at least one of a1 and a2 is 1 or more; b represents 0 or 1; Y is an acyclic divalent saturated hydrocarbon group having 2 to 8 carbon atoms; the saturated hydrocarbon group is a partially fluorinated saturated hydrocarbon group which does not include an ether oxygen atom between carbon atoms, or a non-fluorinated saturated hydrocarbon group which may include an ether oxygen atom between carbon atoms and may have only one polar group, provided that in a case where the non-fluorinated saturated hydrocarbon group has the polar group, the polar group is bonded to a carbon atom other than a bonding terminal of Y; and an oxygen atom at a left terminal of Formula (2) is bonded to a methylene group on an R 1 side in Formula (1), and an oxygen atom at a right terminal is bonded to a methylene group on an R 4 side in Formula (1)).
2 . The fluorine-containing ether compound according to claim 1 ,
wherein Formula (2) is a linking group represented by any of Formulae (2-1) to (2-5),
(in Formula (2-1), all and a12 each represent an integer of 0 to 5; a11 and a12 may be the same as or different from each other; a total value of a11 and a12 is 1 to 6; c represents an integer of 2 to 8; c pieces of R a 's and R b 's each independently represent a hydrogen atom or a methyl group; a total number of carbon atoms included in the c pieces of (—CR a R b —)'s is 2 to 8; and an oxygen atom at a left terminal of Formula (2-1) is bonded to the methylene group on the R 1 side in Formula (1), and an oxygen atom at a right terminal is bonded to the methylene group on the R 4 side in Formula (1))
(in Formula (2-2), a21 and a22 each represent an integer of 0 to 5; a21 and a22 may be the same as or different from each other; a total value of a21 and a22 is 1 to 6; d represents an integer of 2 to 4; d pieces of R c 's each independently represent-CH 2 CH 2 —, —CH 2 CH 2 CH 2 —, —CH(CH 3 )CH 2 —, or —CH 2 CH(CH 3 )—; a total number of carbon atoms included in the d pieces of R c 's is 4 to 8; and an oxygen atom at a left terminal of Formula (2-2) is bonded to the methylene group on the R 1 side in Formula (1), and an oxygen atom at a right terminal is bonded to the methylene group on the R 4 side in Formula (1))
(in Formula (2-3), a31 and a32 each represent an integer of 0 to 5; a31 and a32 may be the same as or different from each other; a total value of a31 and a32 is 1 to 6; e represents an integer of 1 to 6; and an oxygen atom at a left terminal of Formula (2-3) is bonded to the methylene group on the R 1 side in Formula (1), and an oxygen atom at a right terminal is bonded to the methylene group on the R 4 side in Formula (1))
(in Formula (2-4), a41 and a42 each represent an integer of 1 to 5; a41 and a42 may be the same as or different from each other; a total value of a41 and a42 is 2 to 6; f1 and f2 each represent an integer of 1 to 6; f1 and f2 may be the same as or different from each other, and a total value of f1 and f2 is 2 to 7; and an oxygen atom at a left terminal of Formula (2-4) is bonded to the methylene group on the R 1 side in Formula (1), and an oxygen atom at a right terminal is bonded to the methylene group on the R 4 side in Formula (1))
(in Formula (2-5), a51 and a52 each represent an integer of 0 to 5; a51 and a52 may be the same as or different from each other; a total value of a51 and a52 is 1 to 6; and an oxygen atom at a left terminal of Formula (2-5) is bonded to the methylene group on the R 1 side in Formula (1), and an oxygen atom at a right terminal is bonded to the methylene group on the R 4 side in Formula (1)).
3 . The fluorine-containing ether compound according to claim 1 ,
wherein R 1 and R 4 in Formula (1) are each independently a terminal group represented by Formula (3),
(in Formula (3), 1 represents an integer of 1 to 3; 1 pieces of m's each independently represent an integer of 1 to 6; 1 pieces of n's each independently represent an integer of 1 to 6; in one repeating unit, at least one of m and n is 1; and A represents an alkyl group which may have a polar group, an organic group including a carbon-carbon unsaturated bond, which may have a polar group, or a hydrogen atom).
4 . The fluorine-containing ether compound according to claim 1 ,
wherein R 1 and R 4 in Formula (1) are each independently a terminal group represented by Formula (3-1) or (3-2),
(in Formula (3-1), p represents an integer of 0 to 3, q represents an integer of 0 to 2, and r represents an integer of 1 to 5; a total value of p and r is 1 to 5; and B represents a polar group)
(in Formula (3-2), s represents an integer of 0 to 2, and t represents an integer of 1 to 5).
5 . The fluorine-containing ether compound according to claim 1 ,
wherein R 1 and R 4 in Formula (1) are the same as each other.
6 . The fluorine-containing ether compound according to claim 1 ,
wherein a total number of the polar groups contained in R 1 and the polar groups contained in R 4 in Formula (1) is 2 to 6.
7 . The fluorine-containing ether compound according to claim 1 ,
wherein all of the polar groups contained in R 1 , the polar groups contained in R 3 , and the polar groups contained in R 4 in Formula (1) are hydroxy groups.
8 . The fluorine-containing ether compound according to claim 1 ,
wherein the (x+1) pieces of R 2 's in Formula (1) are each independently a perfluoropolyether chain represented by Formula (4),
(CF 2 ) w1 —O—(CF 2 O) w2 —(CF 2 CF 2 O) w3 —(CF 2 CF 2 CF 2 O) w4 —(CF 2 CF 2 CF 2 CF 2 O) w5 —(CF 2 ) w6 — (4)
(in Formula (4), w2, w3, w4, and w5 each indicate an average degree of polymerization and each independently represent 0 to 20, provided that all of w2, w3, w4, and w5 are not 0 at the same time; w1 and w6 are each an average value indicating the number of CF 2 's and each independently represent 1 to 3; and (CF 2 O), (CF 2 CF 2 O), (CF 2 CF 2 CF 2 O), and (CF 2 CF 2 CF 2 CF 2 O), which are repeating units in Formula (4), is not particularly limited in the sequence order).
9 . The fluorine-containing ether compound according to claim 1 ,
wherein the (x+1) pieces of R 2 's in Formula (1) are each independently any one selected from perfluoropolyether chains represented by Formulae (4-1) to (4-4),
—CF 2 —(OCF 2 CF 2 ) h —(OCF 2 ) i —OCF 2 — (4-1)
(in Formula (4-1), h and i each indicate an average degree of polymerization, h represents 1 to 20, and i represents 0 to 20)
—CF 2 CF 2 —(OCF 2 CF 2 CF 2 ) j —OCF 2 CF 2 — (4-2)
(in Formula (4-2), j indicates an average degree of polymerization and represents 1 to 15)
—CF 2 CF 2 CF 2 —(OCF 2 CF 2 CF 2 CF 2 ) k —OCF 2 CF 2 CF 2 — (4-3)
(in Formula (4-3), k indicates an average degree of polymerization and represents 1 to 10)
(CF 2 ) w7 —O—(CF 2 CF 2 CF 2 O) w8 —(CF 2 CF 2 O) w9 —(CF 2 ) w10 — (4-4)
(in Formula (4-4), w8 and w9 each indicate an average degree of polymerization and each independently represent 1 to 20; and w7 and w10 are each an average value indicating the number of CF 2 's and each independently represent 1 or 2).
10 . The fluorine-containing ether compound according to claim 1 ,
wherein the fluorine-containing ether compound has a number-average molecular weight in a range of 500 to 10,000.
11 . A lubricant for a magnetic recording medium, comprising:
the fluorine-containing ether compound according to claim 1 .
12 . A magnetic recording medium comprising, in the following order, on a substrate, at least:
a magnetic layer;
a protective layer; and
a lubricating layer,
wherein the lubricating layer includes the fluorine-containing ether compound according to claim 1 .
13 . The magnetic recording medium according to claim 12 ,
wherein an average film thickness of the lubricating layer is 0.5 nm to 2.0 nm.