Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Patent
1995-09-12
1998-04-21
Shaver, Paul F.
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
556485, 252 6251, 252 6255, 252 6264, 428447, 428450, 428457, 428403, C07F 708
Patent
active
057419221
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to fluorine-containing aromatic compounds and silane coupling agents comprising the compound.
BACKGROUND ART
Composite materials comprising an inorganic material and an organic material in combination are presently used in various fields because of their outstanding properties and sophisticated functions. With composite materials, control of the interface between the different component materials thereof is a very important problem. As one method of control, silane coupling agents are used for modifying the surface of inorganic materials. With the introduction of fluorocarbon chains having peculiar properties such as water or oil repellency, high lubricity and chemical resistance into silane coupling agents, increased attention has been directed to the application of these agents as surface modifying agents having a function different from that of imparting improved adhesion.
For example, magnetic fluids can be obtained pulverization, deflocculation or a process involving adsorption in an aqueous solution and organic phase dispersion. In the case of any of these processes, finely divided magnetite, iron or like ferromagnetic material is given affinity for a solvent by being caused to adsorb a surfactant on the surface for modification and then dispersed in a base oil. However, the magnetic fluid incorporating the surfactant is unsatisfactory in heat resistance, cold resistance, resistance to chemicals, insulating properties, etc. Especially the surfactant used for stabilizing the dispersion of the finely divided ferromagnetic material usually has a hydrophilic group, so that when water or a highly humid gas is sealed with the magnetic fluid, water dissolves in the magnetic fluid, releasing the surfactant from the material and deteriorating the magnetic fluid. Further magnetic fluids wherein a hydrocarbon oil is used as the base oil are -20.degree. C. to 150.degree. C. in the range of heat-resistant temperatures, solidify in a cold climate or deteriorate in a high temperature range owing to oxidation and therefore remain to be improved.
In order to develop a magnetic fluid having a wide heat-resistant temperature range and high water resistance, we have conducted research and found that this purpose can be accomplished by modifying the surface of a finely divided magnetic material with a fluorine-containing aromatic silane coupling agent and dispersing the material is a medium, and also by using a fluorine-containing oil having a wide heat-resistant temperature range as the dispersion medium (base oil).
An object of the present invention is to provide a fluorine-containing aromatic compound which is advantageously usable for preparing a magnetic fluid or the like having a wide heat-resistant temperature range and high water resistance, and a silane coupling agent comprising the compound.
DISCLOSURE OF THE INVENTION
The present invention provides a fluorine-containing aromatic compound represented by the formula (1) ##STR2## wherein X is H, F, Cl, C.sub.1.about.20 alkyl or C.sub.1.about.20 alkoxyl, p is an integer of 1 to 4, Y is --COCH.sub.3, --COOC.sub.2 H.sub.5, --CH(OH) CH.sub.3, --C(CH.sub.3).sub.2 OH, --CH.dbd.CH.sub.2, --C(CH.sub.3).dbd.CH.sub.2, --CAB(CH.sub.2).sub.m Si(CH.sub.3).sub.n Z.sub.3-n, A and B are each H or CH.sub.3, Z is Cl, OCH.sub.3 or OC.sub.2 H.sub.5, and m and n are each 0 or 1, and Rf is C.sub.1.about.20 fluoroalkyl or C.sub.1.about.100 fluoropolyether group.
The invention also provides a fluorine-containing aromatic silane coupling agent comprising a compound of the formula (1) wherein Y is --CAB(CH.sub.2).sub.m Si(CH.sub.3).sub.n Z'.sub.3-n, wherein A, B, m and n are each the same as defined above, and Z' is OCH.sub.3 or OC.sub.2 H.sub.5.
The invention further provides a finely divided magnetic material having its surface modified with the fluorine-containing aromatic silane coupling agent.
According to the invention, examples of C.sub.1.about.20 alkyl groups are methyl, ethyl, propyl, butyl, hexyl, nonyl, dodecyl, heptadecyl, e
REFERENCES:
patent: 5068387 (1991-11-01), Kleyer et al.
patent: 5545255 (1996-08-01), Ogawa
R.A., Benkeser, "Silylation of organic halides. New method of forming the carbon-silicon bond.", A. Amer. Chem. Soc. 1969. 91(13), 3666-7 (Eng), vol. 71, No. 13, Sep. 29, 1969.
Daikin Industries Ltd.
Shaver Paul F.
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