Central Glass Company, Limited

Hitachi, Ltd.

Masamichi Maruta

Hidehisa Nanai

Yoshihiro Moroi

Seiji Hasegawa

Hiroshi Takahashi

Akihiro Fukui

Akira Nagai

Akio Takahashi

Shin Nishimura

Yokusu Kuriyama

Takeshi Kondo

Mineo Watanabe

Takayuki Nishimiya

Hideki Oshio

Takeshi Nakai

Adam C Alty

Richard A Du Boisson

Frank Waters

Tetsuo Wada

Showzou Kaneda

Etsuko Katoh

The present invention provides a novel method for preparing 4,4,4-trifluorobutane-2-one by providing a fluorobutene selected from the group consisting of 2,4,4,4-tetrafluoro-1-butene, (E)-1,1,1,3-tetrafluoro-2-butene, (Z)-1,1,1,3-tetrafluoro-2-butene, and mixture thereof; and reacting the fluorobutene(s) with a proton acid and water.

Method for producing 4,4,4-trifluorobutane-2-one

A polyimide precursor composition which is produced by (i) providing a polyamide acid solution obtained by reacting an aromatic tetracarboxylic acid component and a diamine component in the presence of an oxygen-containing solvent and (ii) subjecting said polyamide acid solution to heat treatment. The polyimide precursor composition exhibits a desirable apparent viscosity and a desirable thixotropic property and it excels in film forming ability, and because of this, it enables the formation a high quality relief pattern film with no defect and which excels in form retention by way of the screen printing. Further, the polyimide precursor composition is extremely suitable for the formation of a relief pattern by way of screen printing in the production of electronic, electric, optical, or precision devices, wherein the relief pattern is required to have a reduced dielectric constant and a reduced residual stress and to have a sufficient heat resistance, moisture resistance, physical strength, and chemical stability.

Polyimide precursor composition, polyimide composition, process for the

A polyimide precursor composition which is produced by (i) providing a polyamide acid solution obtained by reacting an aromatic tetracarboxylic acid component and a diamine component in the presence of an oxygen-containing solvent and (ii) subjecting said polyamide acid solution to heat treatment. The polyimide precursor composition exhibits a desirable apparent viscosity and a desirable thixotropic property and it excels in film forming ability, and because of this, it enables the formation a high quality relief pattern film with no defect and which excels in form retention by way of the screen printing. Further, the polyimide precursor composition is extremely suitable for the formation of a relief pattern by way of the screen printing in production of electronic, electric, optical, or precision devices, wherein the relief pattern is required to have a reduced dielectric constant and a reduced residual stress and to have a sufficient heat resistance, moisture resistance, physical strength, and chemical stability.

Polyimide precursor composition and the production of said polyimide

A polyimide precursor composition solution includes a tetracarboxylic acid component containing not less than 70 mol % of at least one selected from the group consisting of benzenetetracarboxylic acid and its reactive derivatives; a maleimide compound; and a diamine component containing not less than 70 mol % of 2,2'-substituted-4,4'-benzidine represented by the general formula (I) and siloxydiamine amounting to from 1 to 10 mol %. The tetracarboxylic acid component, the maleimide compound and the diamine component are dissolved in a solvent which is consisting essentially of .gamma.-butyrolactone. The amount of the tetracarboxylic acid component is substantially equivalent to that of the diamine component. The amount of the maleimide compound is from 5 to 30 wt % of the total weight of the tetracarboxylic acid and the diamine component. A polyimide coating film prepared from the polyamide precursor solution is very low in residual stress and superior in adhesion to a substrate, has a very flat surface and can be desirably treated by wet etching process with an etching solution which is not hazardous. ##STR1## wherein R are the same or different ones selected from the group consisting of CF.sub.3, CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, Cl, Br and phenyl group.

Low stress polyimide composition and precursor composition solution of

A fluorine-containing thermosetting resin having a three-dimensional crosslinking structure is obtained by polymerizing a bismaleimide compound having the formula, ##STR1## wherein Rf is fluorine, CF.sub.3, C.sub.2 F.sub.5 or C.sub.3 F.sub.7. The resin is excellent in moldability, thermal resistance and electric properties, has a low dielectric constant, is hence suitable as a molding material and can be used for molding materials, wiring boards, layer insulation films of LSI, etc.

Fluorine-containing thermosetting resin

The invention provides novel fluorine-containing bismaleimides represented by the general formula shown below. The bismaleimides are obtained by dehydrating and cyclizing reaction of corresponding bismaleamic acids which are also novel compounds. For example, maleic anhydride is used for preparing the bismaleamic acids. A mixture of a bismaleimide of the invention and a diamine is useful as a thermosetting resin composition. At 100.degree.-300.degree. C. the resin composition undergoes addition polymerization to turn into a solid resin which are high in moisture resistance and low in dielectric constant. For use in the resin composition it is preferable that both R.sup.1 and R.sup.2 in the general formula of the bismaleimide are --CF.sub.3. ##STR1## wherein A represents a divalent organic group having an ethylenic unsaturated bond; Rf represents fluorine atom or a perfluoroalkyl group; R.sup.1 and R.sup.2 are the same or different and each represent hydrogen atom, methyl group, ethyl group or a halogenated methyl group; and each -N&lt; is at the m- or p-position with respect to the aromatic ether bond --O--.

Fluorine-containing bismaleamic acids and bismaleimides useful for

By reacting fluorobenzene with hexafluoroacetone in the pressure of a Lewis acid catalyst, e.g. aluminum chloride, a novel compound 2,4-bis(2-hydroxyhexafluoro-2-propyl)fluorobenzene is formed at high yield with little formation of isomers. The novel compound is useful as a cross-linking agent for some polymers and also as a material of some polymers.

2,4-bis(2-hydroxyhexafluoro-2-propyl)fluorobenzene and method of

2,2-Bis(4-aminophenyl)hexafluoropropane is prepared by the steps of (a) reacting 2,2-bis(4-carboxyphenyl)hexafluoropropane with thionyl chloride at 80.degree.-150.degree. C. in a water insoluble organic liquid in the presence of a catalyst such as dimethylformamide to obtain a solution of 2,2-bis(4-chloroformylphenyl)hexafluoropropane, (b) mixing the obtained solution with an aqueous solution of sodium azide to obtain an acid azide solution, (c) heating the organic phase of the acid azide solution to 80.degree. C. or above to cause rearrangement of the acid azide into an isocyanate, (d) hydrolyzing the isocyanate by mixing the isocyanate solution with an acid such as 40-80% sulfuric acid to form a salt of the aimed diamine as an aqueous solution mixed with an organic phase, and (e) neutralyzing the aqueous solution separated from the liquid mixture obtained at step (d) to precipitate the aimed diamine. This process is favorable for industrial practice because the main steps (a) to (d) are all reactions in organic liquids without precipitating solid intermediates.

Process of preparing 2,2-bis(4-aminophenyl)-hexafluoropropane

Disclosed herein is a method of producing 2,2-bis(3-nitro-4-hydroxphenyl)hexafluoropropane, which comprises (a) preparing 2,2-bis(4-hydroxyphenyl)hexafluoropropane and a lower fatty acid; and (b) allowing the 2,2-bis(4-hydroxyphenyl)hexafluoropropane to react with nitric acid in the lower fatty acid.

Method of producing 2,2-bis(3-nitro-4-hydroxyphenyl)hexafluoropropane

Polyfluoroenolates, R.sup.1 CX.dbd.CR.sup.2 OM (R.sup.1 is F or a perfluoroalkyl group, R.sup.2 is a perfluoroalkyl group, X is F, Cl or Br), are easily formed at good yields by dehydrohalogenation reaction of polyfluoroalcoholates, R.sup.1 CXY--CR.sup.2 HOM (Y is F, Cl or Br), with a strong base such as, e.g., an alkyl metal or an aryl metal. A typical example of the polyfluoroenolates is lithium pentafluoro-2-propenolate which is obtained from hexafluoro-2-propanolate. A polyfluoroenolate of the above general formula can be converted into another polyfluoroenolate having an alkyl or aryl group in place of the halogen X by reaction with an alkyl or aryl metal.

Preparation of polyfluoroenolates

Trifluoroacetic acid is easily formed by hydrolysis of 1,1,1-trichloro-2,2,2-trifluoroethane with water in the presence of a catalyst comprising an inorganic metal compound, preferably a chloride of Mn, Fe, Co, Ni, Cu or Zn. Preferably the hydrolysis reaction is carried out as a vapor phase contact reaction at 200.degree.-400.degree. C., using 5-15 moles of water per mole of trichlorotrifluoroethane.

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Kawagoe, Japan

Masamichi Maruta