Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From fluorine-containing reactant
Reexamination Certificate
1999-07-16
2001-01-09
Truong, Duc (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From fluorine-containing reactant
C528S397000, C528S205000, C528S206000, C528S220000
Reexamination Certificate
active
06172181
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a novel (2,3,4,5,6-pentafluorobenzoyl) diphenyl ether compound and a novel fluorine-containing aryl ether ketone polymer.
2. Description of the Related Art
The high-performance fluorinated polymers have been receiving considerable attention as interesting advanced materials for applications as films, coatings for optical and microelectronics devices, gas separation membranes and so on (Cassidy, P. E., Aminabbai, T. M. and Farley, J. M.,
J. Macromol. Sci.-Rev. Macromol. Chem. Phys.
C29 (2 & 3), 365-429 (1989)). The incorporation of fluorine atoms into polymer chains leads to polymers with increased solubility, flame resistance, thermal stability and glass transition temperature while also leading to decreased color, crystallinity, dielectric constant and moisture absorption. Owing these advantages, poly(aryl ether ketone)s (PEK) containing hexafluoroisopropylidene units had been prepared and studied for the use in aerospace and electronic applications (Tullos, G. L. and Cassidy, P. E.,
Macromolecules,
24, 6059 (1991)). Recently, PEK's containing perfluophenylene moieties were synthesized from perfluorobenzophenone (Mercer, F. W., Fone, M. M., Reddy, V. N., and Goodwin, A. A.,
Polymer,
38 (8), 1989 (1997)).
These polymers, however, are still deficient in solubility and flame resistance.
An object of this invention, therefore, is to provide a novel (2,3,4,5,6-pentafluorobenzoyl)diphenyl ether compound for the use as a raw material of a novel fluorine-containing aryl ether ketone polymer exhibiting high mechanical strength and toughness and excelling in electrical properties, thermal oxidative stability, and solubility.
Another object of this invention is to provide a novel fluorine-containing aryl ether ketone polymer.
Yet another object of this invention is to provide a fluorine-containing aryl ether ketone polymer exhibiting high mechanical strength and toughness and excelling in electrical properties, thermal oxidative stability, and solubility.
SUMMARY OF THE INVENTION
These objects can be accomplished by the following items (1) and (2).
(1) A (2,3,4,5,6-pentafluorobenzoyl)diphenyl ether compound represented by the formula (I):
wherein R stands for a hydroxyl group or a group represented by the
formula:
(2) A fluorine-containing aryl ether ketone polymer represented by the formula (II):
wherein n stands for a degree of polymerization, m is an integer of 0 or 1, and R
1
stands for a group represented by the formula (III):
wherein p is an integer 0or 1 and R
2
stands for
The (2,3,4,5,6-pentafluorobenzoyl)diphenyl ether compound of this invention, by being subjected to the reaction of polycondensation or to the reaction of co-condensation polymerization with a divalent phenol compound as described specifically herein below, can provide a novel fluorine-containing aryl ether ketone polymer exhibiting high mechanical strength and toughness and excelling in electrical properties, thermal oxidative stability, and solubility.
The fluorine-containing aryl ether ketone polymer of this invention are not only useful as a coating agent for electronic parts but also suitable for cast products because they possess high mechanical strength and toughness, excellent electrical properties, perfect solubility in various solvents in popular use, excellent thermal stability such as heat resistance and flame resistance, and excellent film-forming ability.
The above and other objects, features and advantages of the present invention will become clear from the following description of the preferred embodiments.
REFERENCES:
Cassidy et al., “Polymers Derived from Hexafluoroacetone”, JMS-Rev. Macromol. Chem. Phys., c29(2&3), 365-429 (1989).
Kimura et al., “New Polymers Derived from 2,3,4,5,6-pentafluorobenzoic Acid”, Chemical Abstract 129:260978, 1999.
Mercer et al., “Synthesis and Characterization of Fluorinated Polyetherketones Prepared From Decafluorobenzophenone”, Polymer, vol. 38, No. 8, pp. 1989-1995, (1997).
Tullos, et al., “Polymers Derived from Hexafluoroacetone: 12F-Poly(ether ketone)”, Macromolecules, vol. 24, pp. 6059-6064 (1991).
Cassidy Patrick E.
Fitch, III John W.
Kimura Kunio
Reddy V. Sreenivasulu
Yamashita Yuhiko
Fish & Richardson P.C.
Nippon Shokubai Co. , Ltd.
Truong Duc
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