Celanese Gmbh

Hoechst Celanese Corporation

Harry T Hanson

John B Sapp, Jr

Edward C Chenevey

Marvin Gordon

Provided is a novel and effective process for the synthesis of aryl sulfides substituted with an alkanoylamino or (N-alkyl)alkanoylamino substituent. The process comprises reacting an appropriately substituted aromatic compound with a sulfur dihalide, preferably sulfur dichloride, in the presence of an alkali metal tetrafluoroborate catalyst and an ether comprising solvent.

Synthesis of substituted aryl sulfides

Novel poly-aromatic ethynyl-terminated enyne compounds of the formula: ##STR1## are provided together with a method of production thereof, wherein R.sub.1 is a strong electron withdrawing moiety and n is equal to or greater than 1.

Acetylene-terminated aromatic enyne resins and method of production

Accelerated curing rates of certain acetylene-terminated aromatic sulfones and polyimide oligomers are obtained by thermally curing the resins with an effective amount of a diethynylbiphenyl.

Method of accelerating cure rates for acetylene-terminated resins and

Provided is a novel process for the synthesis of aryl sulfides substituted with an alkoxy or phenoxy substituent. The process comprises reacting an alkoxy or phenoxy substituted aromatic compound with a sulfur dihalide, preferably sulfur dichloride, in the presence of an alkali metal tetrafluoroborate catalyst, with the amount of said aromatic reactant compound preferably being sufficient to solvate the sulfur dichloride and catalyst sufficiently to allow the reaction to occur.

Synthesis of alkoxy and phenoxy substituted aryl sulfides

In one aspect, thermosetting liquid resinous polyepoxides are upgraded or advanced in molecular weight by a process including (A) providing a catalyst-free mixture of a dihydric phenol, preferably bisphenol-A and a liquid resinous polyepoxide containing 1,2-epoxy groups, preferably a low molecular weight epoxy resin consisting essentially of the diglycidyl ether of bisphenol-A, at a temperature above about a minimum reaction temperature for a catalytic liquid upgrade reaction between the dihydric phenol and the polyepoxide; and (B) subsequently introducing the catlyst, preferably an organic phosphine and most preferably triphenylphosphine, into the mixture of the dihydric phenol and polyepoxide at reaction temperature and maintaining the mixture containing the catalyst at reaction temperature for a time sufficient to produce the upgraded version of the thermosetting resinous polyepoxide. In another aspect, multiple catalyst additions are featured wherein, for example, after a first catalytic amount of a catalyst is introduced into the mixture of dihydric phenol and polyepoxide and the reaction has been maintained for a first period of time, a second catalytic amount of the catalyst is introduced into the mixture while at reaction temperature to upgrade further the polyepoxide. In yet another aspect of the disclosure, thermosetting resinous polyepoxides of improved molecular weight distribution are obtained by a process, preferably a continuous process, which involves (A) providing a catalyst-free mixture of bisphenol-A and a liquid resinous polyepoxide consisting essentially of an aromatic polyepoxide of the structural formula: ##STR1## to a temperature between 120.degree. C. and about 200.degree. C.; and (B) subsequently introducing triphenylphosphine into the mixture of the dihydric phenol and aromatic polyepoxide at a reaction temperature above 120.degree. C. and maintaining the mixture containing the catalyst at reaction temperature for a time between about 5 and about 30 minutes.

Production of thermosetting resinous polyepoxides

An improved overall process is provided wherein poly(bisbenzimidazobenzophenanthroline) is formed on an expeditious basis and is recovered from the reaction mass in substantially pure form. Appropriate quantities of 1,4,5,8-tetracarboxy naphthalene dianhydride and 3,3',4,4' -tetraaminobiphenyl are condensed as defined) in a reaction zone while dissolved in molten antimony trichloride, and the resulting reaction mass containing the dissolved product is discharged into a precipitation zone containing hydrochloric acid (as defined). The resulting solid product is separated and dried. The liquid portion which is separated from the solid product contains antimony trichloride dissolved in hydrochloric acid and is subjected to distillation which substantially separates these components. The antimony trichloride is recycled to the reaction zone, and the hydrochloric acid is recycled to the precipitation zone.

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Millburn, NJ, United States of America

Harry T Hanson