US 6,019,909 AGranted

Fluorinated hydrocarbon compound and process for its preparation, and refrigerator oil and magnetic recording medium lubricant

AssigneeDaikin Industries, Ltd.

InventorsSatoshi Ide, Katsuki Fujiwara, Masayuki Yamana, Yoshitaka Honda, Ikuo Yamamoto, Fumihiko Yamaguchi, Eiji Seki, Tatsuya Otsuka, Satoshi Ishida

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Abstract

A novel fluorinated hydrocarbon compound containing an oxygen or sulfur atom in its molecule, produced by the nucleophilic reaction of a fluorine compound with a hydrocarbon compound. This compound is useful as a lubricant for various applications and particularly excellent as an oil for refrigerators wherein hydrochlorofluorocarbon is used as the refrigerant and as a magnetic recording medium lubricant.

Claims16

Dependent claims

A fluorinated hydrocarbon compound having at least one oxygen atom in the molecule and represented by the formula (II)

(R.sup.5 O).sub.d R.sup.6
wherein d is 1 or 2, R.sup.5 is selected from the group consisting of
(CF.sub.3).sub.2 CF(CF.sub.2 CF.sub.2).sub.n CH.sub.2 CH.sub.2 OCH.sub.2 CH(OH)CH.sub.2 -- (n=integer of 0-10),
CF.sub.3 CF.sub.2 (CF.sub.2 CF.sub.2).sub.m CH.sub.2 CH.sub.2 OCH.sub.2 CH(OH)CH.sub.2 -- (m=integer of 0-10),
H(CF.sub.2 CF.sub.2).sub.l CH.sub.2 CH.sub.2 CH(OH)CH.sub.2 -- (l=integer of 0-10),
(CF.sub.3).sub.2 CF(CF.sub.2 CF.sub.2).sub.k CH.sub.2 CH(OH)CH.sub.2 -- (k=integer of 0-10), or
CF.sub.3 CF.sub.2 (CF.sub.2 CF.sub.2).sub.j CH.sub.2 CH(OH)CH.sub.2 -- (j=integer of 0-10)
(CF.sub.3).sub.2 CF(CF.sub.2 CF.sub.2).sub.a CH.sub.2 CH.sub.2 -- (a=integer of 0-10),
CF.sub.3 CF.sub.2 (CF.sub.2 CF.sub.2).sub.b CH.sub.2 CH.sub.2 -- (b=integer of 0-10), or
H(CF.sub.2 CF.sub.2).sub.c CH.sub.2 -- (c=integer of 1-10),
HCF.sub.2 CF.sub.2 --, HCClFCF.sub.2 --, HCF.sub.2 CClF--, CF.sub.3 CFHCF.sub.2 --, CF.sub.3 CF.dbd.CF--,
CF.sub.2 .dbd.CFCF.sub.2 --, CH.sub.3 CF.sub.2 --, (CF.sub.3).sub.2 CHCF.sub.2 --, HOC(CF.sub.3).sub.2 --,
Cl(CF.sub.2 CClF).sub.i CFHCClF-- (i=integer of 1-20) ##STR119## wherein x, y, z, v and w are each an integer of 0 to 100, provided that they can not be zero at the same time, or
R.sup.8 (CF(CF.sub.3)CF.sub.2 O).sub.p (CF.sub.2 CF.sub.2 O).sub.q (CF.sub.2 O).sub.r R.sup.9 --
wherein p, q and r are each an integer of 0 to 100, provided that they can not be zero at the same time, and when d is 1 R.sup.6 is
C.sub.n H.sub.2n+1 -- (n=integer of 10-30),
C.sub.m H.sub.2m-1 -- (m=integer of 10-30),
C.sub.h H.sub.2h-3 -- (h=integer of 10-30),
ClC.sub.l H.sub.2l -- (l=integer of 1-10),
Cl(CH.sub.2).sub.7 CH.dbd.CH(CH.sub.2).sub.8 --
CH.sub.3 (OCH.sub.2 CH.sub.2).sub.k -- (k=integer of 1-100), ##STR120## (j=integer of 1-100), ##STR121## (i=integer of 1-100), ##STR122## (p=integer of 1-100), ##STR123## (q=integer of 1-100 and r=integer of 0-10), ##STR124## (s=integer of 1-100), and when d is 2 R.sup.6 represents
--(C.sub.h H.sub.2h)-- (h=integer of 1-10) ##STR125## (t=integer of 1-100) wherein t is an integer of 1 to 100, provided that combinations of R.sup.5 and R.sup.6 are excluded when R.sup.5 is ##STR126## and R.sup.6 is --(CH.sub.2).sub.4 --.

19 more elements

A lubricant comprising at least one fluorinated hydrocarbon compound having at least one oxygen atom in the molecule and selected from the group consisting of:

a fluorinated hydrocarbon compound having at least one oxygen atom in the molecule and represented by the formula (II)
(R.sup.5 O).sub.d R.sup.6
wherein d is 1 or 2, R.sup.5 is
(CF.sub.3).sub.2 CF(CF.sub.2 CF.sub.2).sub.n CH.sub.2 CH.sub.2 OCH.sub.2 CH(OH)CH.sub.2 -- (n=integer of 0-10),
CF.sub.3 CF.sub.2 (CF.sub.2 CF.sub.2).sub.m CH.sub.2 CH.sub.2 OCH.sub.2 CH(OH)CH.sub.2 -- (m=integer of 0-10),
H(CF.sub.2 CF.sub.2).sub.l CH.sub.2 CH.sub.2 CH(OH)CH.sub.2 -- (l=integer of 0-10),
(CF.sub.3).sub.2 CF(CF.sub.2 CF.sub.2).sub.k CH.sub.2 CH(OH)CH.sub.2 -- (k=integer of 0-10), or
CF.sub.3 CF.sub.2 (CF.sub.2 CF.sub.2).sub.j CH.sub.2 CH(OH)CH.sub.2 -- (j=integer of 0-10)
(CF.sub.3).sub.2 CF(CF.sub.2 CF.sub.2).sub.a CH.sub.2 CH.sub.2 -- (a=integer of 0-10),
CF.sub.3 CF.sub.2 (CF.sub.2 CF.sub.2).sub.b CH.sub.2 CH.sub.2 -- (b=integer of 0-10), or
H(CF.sub.2 CF.sub.2).sub.c CH.sub.2 -- (c=integer of 1-10),
HCF.sub.2 CF.sub.2 --, HCClFCF.sub.2 --, HCF.sub.2 CClF--, CF.sub.3 CFHCF.sub.2 --, CF.sub.3 CF.dbd.CF--,
CF.sub.2 .dbd.CFCF.sub.2 --, CH.sub.3 CF.sub.2 --, (CF.sub.3).sub.2 CHCF.sub.2 --, HOC(CF.sub.3).sub.2 --,
Cl(CF.sub.2 CClF).sub.i CFHCClF-- (i=integer of 1-20) ##STR151## wherein x, y, z, v and w are each an integer of 0 to 100, provided that they can not be zero at the same time, or R.sup.8 (CF(CF.sub.3)CF.sub.2 O).sub.p (CF.sub.2 CF.sub.2 O).sub.q (CF.sub.2 O).sub.r R.sup.9 -- wherein p, q and r are each an integer of 0 to 100, provided that they can not be zero at the same time, and when d is 1 R.sup.6 is
C.sub.n H.sub.2n+1 -- (n=integer of 10-30),
C.sub.m H.sub.2m-1 -- (m=integer of 10-30),
C.sub.h H.sub.2h-3 -- (h=integer of 10-30),
ClC.sub.l H.sub.2l -- (l=integer of 1-10),
Cl(CH.sub.2).sub.7 CH.dbd.CH(CH.sub.2).sub.8 --
CH.sub.3 (OCH.sub.2 CH.sub.2).sub.k -- (k=integer of 1-100), ##STR152## (j=integer of 1-100), ##STR153## (i=integer of 1-100), ##STR154## (p=integer of 1-100), ##STR155## (q=integer of 1-100 and r=integer of 0-10), ##STR156## (s=integer of 1-100), and when d is 2 R.sup.6 represents
--(C.sub.h H.sub.2h)-- (h=integer of 1-10) ##STR157## (t=integer of 1-100) wherein t is an integer of 1 to 100, provided that combinations of R.sup.5 and R.sup.6 are excluded when R.sup.5 is ##STR158## and R.sup.6 is --(CH.sub.2).sub.4 --.

18 more elements

An oil for a refrigerating machine which uses as a refrigerant a hydrogen-containing halogenated hydrocarbon, the oil comprising at least one fluorinated hydrocarbon compound having at least one oxygen atom in the molecule and selected from the group consisting of:

a fluorinated hydrocarbon compound having at least one oxygen atom in the molecule and represented by the formula (II)
(R.sup.5 O).sub.d R.sup.6
wherein d is 1 or 2, R.sup.5 is
(CF.sub.3).sub.2 CF(CF.sub.2 CF.sub.2).sub.n CH.sub.2 CH.sub.2 OCH.sub.2 CH(OH)CH.sub.2 -- (n=integer of 0-10),
CF.sub.3 CF.sub.2 (CF.sub.2 CF.sub.2).sub.m CH.sub.2 CH.sub.2 OCH.sub.2 CH(OH)CH.sub.2 -- (m=integer of 0-10),
H(CF.sub.2 CF.sub.2).sub.l CH.sub.2 CH.sub.2 CH(OH)CH.sub.2 -- (l=integer of 0-10),
(CF.sub.3).sub.2 CF(CF.sub.2 CF.sub.2).sub.k CH.sub.2 CH(OH)CH.sub.2 -- (k=integer of 0-10), or
CF.sub.3 CF.sub.2 (CF.sub.2 CF.sub.2).sub.j CH.sub.2 CH(OH)CH.sub.2 -- (j=integer of 0-10)
(CF.sub.3).sub.2 CF(CF.sub.2 CF.sub.2).sub.a CH.sub.2 CH.sub.2 -- (a=integer of 0-10),
CF.sub.3 CF.sub.2 (CF.sub.2 CF.sub.2).sub.b CH.sub.2 CH.sub.2 -- (b=integer of 0-10), or
H(CF.sub.2 CF.sub.2).sub.c CH.sub.2 -- (c=integer of 1-10),
HCF.sub.2 CF.sub.2 --, HCClFCF.sub.2 --, HCF.sub.2 CClF--, CF.sub.3 CFHCF.sub.2 --, CF.sub.3 CF.dbd.CF--,
CF.sub.2 .dbd.CFCF.sub.2 --, CH.sub.3 CF.sub.2 --, (CF.sub.3).sub.2 CHCF.sub.2 --, HOC(CF.sub.3).sub.2 --,
Cl(CF.sub.2 CClF).sub.i CFHCClF-- (i=integer of 1-20) ##STR159## wherein x, y, z, v and w are each an integer of 0 to 100, provided that they can not be zero at the same time, or R.sup.8 (CF(CF.sub.3)CF.sub.2 O).sub.p (CF.sub.2 CF.sub.2 O).sub.q (CF.sub.2 O).sub.r R.sup.9 --wherein p, q and r are each an integer of 0 to 100, provided that they can not be zero at the same time, and when d is 1 R.sup.6 is
C.sub.n H.sub.2n+1 -- (n=integer of 10-30),
C.sub.m H.sub.2m-1 -- (m=integer of 10-30),
C.sub.h H.sub.2h-3 -- (h=integer of 10-30),
ClC.sub.l H.sub.2l -- (l=integer of 1-10),
Cl(CH.sub.2).sub.7 CH.dbd.CH(CH.sub.2).sub.8 --
CH.sub.3 (OCH.sub.2 CH.sub.2).sub.k -- (k=integer of 1-100), ##STR160## (j=integer of 1-100), ##STR161## (i=integer of 1-100), ##STR162## (p=integer of 1-100), ##STR163## (q=integer of 1-100 and r=integer of 0-10), ##STR164## (s=integer of 1-100) and when d is 2 R.sup.6 represents
--(C.sub.h H.sub.2h)-- (h=integer of 1-10) ##STR165## (t=integer of 1-100) wherein t is an integer of 1 to 100, provided that combinations of R.sup.5 and R.sup.6 are excluded when R.sup.5 is ##STR166## and R.sup.6 is --(CH.sub.2).sub.4 --.

18 more elements

A lubricant for magnetic recording media which comprises at least one fluorinated hydrocarbon compound having at least one oxygen atom in the molecule and selected from the group consisting of:

a fluorinated hydrocarbon compound having at least one oxygen atom or a sulfur atom in the molecule and represented by the formula (II)
(R.sup.5 O).sub.d R.sup.6
wherein d is 1 or 2, R.sup.5 is
(CF.sub.3).sub.2 CF(CF.sub.2 CF.sub.2).sub.n CH.sub.2 CH.sub.2 OCH.sub.2 CH(OH)CH.sub.2 -- (n=integer of 0-10),
CF.sub.3 CF.sub.2 (CF.sub.2 CF.sub.2).sub.m CH.sub.2 CH.sub.2 OCH.sub.2 CH(OH)CH.sub.2 -- (m=integer of 0-10),
H(CF.sub.2 CF.sub.2).sub.l CH.sub.2 CH.sub.2 CH(OH)CH.sub.2 -- (l=integer of 0-10),
(CF.sub.3).sub.2 CF(CF.sub.2 CF.sub.2).sub.k CH.sub.2 CH(OH)CH.sub.2 -- (k=integer of 0-10), or
CF.sub.3 CF.sub.2 (CF.sub.2 CF.sub.2).sub.j CH.sub.2 CH(OH)CH.sub.2 -- (j=integer of 0-10)
(CF.sub.3).sub.2 CF(CF.sub.2 CF.sub.2).sub.a CH.sub.2 CH.sub.2 -- (a=integer of 0-10),
CF.sub.3 CF.sub.2 (CF.sub.2 CF.sub.2).sub.b CH.sub.2 CH.sub.2 -- (b=integer of 0-10), or
H(CF.sub.2 CF.sub.2).sub.c CH.sub.2 -- (c=integer of 1-10),
HCF.sub.2 CF.sub.2 --, HCClFCF.sub.2 --, HCF.sub.2 CClF--, CF.sub.3 CFHCF.sub.2 --, CF.sub.3 CF.dbd.CF--,
CF.sub.2 .dbd.CFCF.sub.2 --, CH.sub.3 CF.sub.2 --, (CF.sub.3).sub.2 CHCF.sub.2 --, HOC(CF.sub.3).sub.2 --,
Cl(CF.sub.2 CClF).sub.i CFCClF-- (i=integer of 1-20) ##STR167## wherein x, y, z, v and w are each an integer of 0 to 100, provided that they can not be zero at the same time, or R.sup.8 (CF(CF.sub.3)CF.sub.2 O).sub.p (CF.sub.2 CF.sub.2 O).sub.q (CF.sub.2 O).sub.r R.sup.9 --wherein p, q and r are each an integer of 0 to 100, provided that they can not be zero at the same time, and when d is 1 R.sup.6 is
C.sub.n H.sub.2n+1 -- (n=integer of 10-30),
C.sub.m H.sub.2m-1 -- (m=integer of 10-30),
C.sub.h H.sub.2h-3 -- (h=integer of 10-30),
ClC.sub.l H.sub.2l -- (l=integer of 1-10),
Cl(CH.sub.2).sub.7 CH.dbd.CH(CH.sub.2).sub.8 --
CH.sub.3 (OCH.sub.2 CH.sub.2).sub.k -- (k=integer of 1-100), ##STR168## (j=integer of 1-100), ##STR169## (i=integer of 1-100), ##STR170## (p=integer of 1-100), ##STR171## (q=integer of 1-100 and r=integer of 0-10), ##STR172## (s=integer of 1-100) and when d is 2 R.sup.6 represents
--(C.sub.h H.sub.2h)-- (h=integer of 1-10) ##STR173## (t=integer of 1-100) wherein t is an integer of 1 to 100, provided that combinations of R.sup.5 and R.sup.6 are excluded when R.sup.5 is ##STR174## and R.sup.6 is --(CH.sub.2).sub.4 --.

18 more elements

Dependencies are inferred from the claim text.