Occidental Chemical Corporation

Other

Robert A Buchanan

Jeffrey S Stults

Henry C Lin

Robert L Ostrozynski

Ramesh Krishnamurti

Ronald F Spohn

David C Johnson

Habib Hichri

Disclosed is a method of making m-chlorobenzotrifluoride. Benzotrifluoride is reacted with chlorine gas in the presence of about 0.1 to about 5 mole % (based on benzotrifluoride) of a metal chloride which can be FeCl.sub.3, SbCl.sub.3, or AlCl.sub.3 and about 0.025 to about 5.0 mole % (based on benzotrifluoride) of a catalyst having the formula ##STR1## where Z is halogen, alkyl from C.sub.1 to C.sub.6, alkoxy from C.sub.1 to C.sub.6, or fluoroalkyl from C.sub.1 to C.sub.6, n is 0 to 5, and the molar ratio of metal chloride to cocatalyst is about 0.5 to about 4.

Method of making m-chlorobenzotrifluoride

Disclosed are bis-meta-benzotrifluoride compounds having the general formula ##STR1## where each A is independently selected from the group consisting of NO.sub.2, NH.sub.2, and NH.sub.3.sup.+ Z.sup.-, Z.sup.- is an anion and B is selected from the group consisting of O, CO, S, SO, and SO.sub.2. The diamine compounds are useful as monomers in making polyimides, polyamide-imides, and polyamides.

Bis-m-benzotrifluoride compounds

Polyimide polymers of the following recurring structure and the corresponding polyamic acids are disclosed: ##STR1## wherein AR.sub.1 is ##STR2## where X is O, S, SO, SO.sub.2, CO, C(CF.sub.3).sub.2, C(CH.sub.3).sub.2, Si(CH.sub.3).sub.2, or a single bond, wherein AR.sub.2 may be pyromellitic dianhydride, a substituted pyromellitic dianhydride, naphthanoic dianhydride, or ##STR3## where Y is O, S, SO, SO.sub.2, CO, C(CF.sub.3).sub.2, C(CH.sub.3).sub.2, Si(CH.sub.3).sub.2 --O--AR--O--, or a single bond, where AR is an aromatic nucleus.

Polyimides containing fluorine

A process for the preparation of 4,4'-dinitro-2,2'-di(trifluoromethyl)diphenyl ether according to the equation ##STR1## where X is F, Cl, Br or I, where the inorganic base is selected from the group consisting of alkali metal hydroxides, alkali metal carbonates, and alkali metal bicarbonates, in the presence of a catalytic quantity of a benzoate catalyst. 2,8-Dinitro-6,6,12,12,-tetrafluoro-6H,12H-dibenzo[b,f][1,5]dioxocin, the corresponding diamine and polyimides formed from the diamine are also disclosed.

Method for ether formation

Disclosed are glycidyl diamines having the formulas ##STR1## where n is 1 or 2, m is 0, 1, or 2, X is Y or ##STR2## and Y is --, O, S, SO, SO.sub.2, CO, C(CH.sub.3).sub.2, or C(CF.sub.3).sub.2. An epoxy resin can be made by mixing the glycidyl diamine with an epoxy curing agent. The epoxy resins can be used as adhesives or to make composites.

Glycidyl diamines containing aromatic trifluoromethyl group and epoxy

A process for the preparation of 1,1'-oxy-bis(3-trifluoromethyl-4-nitrobenzene) which comprises reacting a compound of the formula ##STR1## where X is F, Cl, Br or I; with an inorganic base selected from the group consisting of alkali metal hydroxides, alkali metal carbonates, and alkali metal bicarbonates, in the presence of a catalytic quantity of a benzoate catalyst. In addition, benzoate esters of 4-nitro-3-trifluoromethylphenol may be isolated.

This invention relates to novel fluorinated N,N-bis-imides of the formula ##STR1## wherein R is a bivalent radical of the formula ##STR2## The compounds are particularly useful as monomers in the preparation of high performance polymer.

Fluorinated N,N-bis-imides

A process for the production of diaryl ethers which comprises heating, to a temperature of 80.degree. C. to 220.degree. C., a compound of the formula ##STR1## wherein X and Y are selected from the group consisting of H, CN, CO.sub.2 H, CHO, NO.sub.2, and CF.sub.3, provided that both X and Y may not simultaneously be H, in a solvent, in the presence of an inorganic base selected from the group consisting of the alkali metal carbonates, bicarbonates, and hydroxides, and in the presence of a catalyst selected from the group consisting of benzoic acid, substituted benzoic acids, C2-C4 aliphatic carboxylic acids, and alkali metal salts of said acids.

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Grand Island, NY, United States of America

Robert A Buchanan