General Electric Company

Charles M Orlando

Jimmy Lynn Webb

Francois A Lavallee

Howard J Klopfer

William K Cleveland

George R Loucks

Philip L Kinson

Russell A Gardner

Cleveland William K S

Asymmetrical bisphenols such as 2-(3-hydroxyphenyl)-2-(4-hydroxyphenyl)propane are prepared by an improved process wherein a hydroxyphenyldialkylcarbinol is reacted with a phenol in the presence of a hydrogen halide catalyst. According to the improved process, the carbinol is added to a mixture of the phenol and hydrogen halide under conditions maintaining a low carbinol concentration in the reaction mixture. This low concentration is preferably maintained by adding the carbinol in the form of a solution in a portion of the phenol.

Process for preparation of asymmetrical bisphenols

The preparation of hydroxyaryldialkylcarbinols by the reaction of hydroxyaryl alkyl ketones or alkyl hydroxyarenecarboxylates with Grignard reagents in a mixed ether-aromatic hydrocarbon solvent is frequently difficult on a large-scale basis because of formation of a voluminous precipitate of mixed magnesium salt. In an improvement in this process, a solution of the ketone or ester in an ether is added to the solution of the Grignard reagent.

Process for preparation of hydroxyaryldialkylcarbinols

A method is described for dehydrochlorinating 1,1,1-trichloro-2,2-bis(4-hydroxyphenyl)ethane employing a refluxing dipolar aprotic solvent, such as dimethylformamide, containing a lithium halide catalyst to produce a crystalline product consisting essentially of 1,1-dichloro-2,2-bis(4-hydroxyphenyl)ethylene. The crystalline product can be isolated in substantially pure form and converted to a high impact, flame retardant polycarbonate.

1,1-Dichloro-2,2-bis(hydroxyphenyl)ethylene

Polycarbonate copolymers are provided consisting essentially of chemically combined bisphenol carbonate units and having from about 5 to 70 mole percent of such chemically combined bisphenol carbonate units in the form of o,p'-bisphenol dichloroethylene carbonate units. The polycarbonate copolymers have been found to possess valuable flame retardant properties and improved processability.

Polycarbonate copolymers

Method for dehydrochlorinating

Phenyl trichloro-ethanes can be prepared by reacting chloral with a phenol compound, such as phenol itself or 2,6-xylenol in HF, which acts both as a catalyst and solvent medium.

Process for preparing phenyl trichloro-ethanes

Monomeric and polymeric halogenated organic compounds derived from 2,2',6,6'-tetrabromo-3,3',5,5' -tetraalkyl-4,4'-biphenols are described. The derivatives are useful in their monomeric and polymeric form as flame retardant additives and/or concentrates for normally flammable resinous materials. The thermal stability at elevated temperatures of the brominated biphenol derivatives advantageously benefits polymeric compositions containing the brominated biphenol derivatives especially when the polymeric compositions are molded into three dimensional articles, or formed into films, sheeting or shaped into fibers, laminates or reinforced plastics by conventional techniques.

Brominated biphenol derivatives

A method is described for dehydrochlorinating 1,1,1-trichloro-2,2-bis(4-hydroxyphenyl)ethane employing a refluxing dipolar aprotic solvent, such as dimethylformamide, containing a lithium halide catalyst to produce a crystalline product consisting essentially of 1,1-dichloro-2,2-bis(4-hydroxyphenyl) ethylene. The crystalline product can be isolated in substantially pure form and converted to a high impact, flame retardant polycarbonate.

Brominated biphenols are produced by a bromination process which comprises reacting bromine with a 3,3', 5,5'-tetrasubstituted diphenoquinone at a temperature below about +20.degree. C. in the presence of an inert diluent, evolving hydrogen bromide gas at a temperature of about +20.degree. C. or lower, heating the resulting reaction mixture at elevated temperatures to complete the bromination reaction and recovering the desired 2,2',6,6'-tetrabromo-3,3',5,5'-tetrasubstituted-4,4'-biphenol. The biphenol products of the process can be used as antioxidants, as monomeric starting materials for polymeric halogenated organic compounds which are fire retardant as well as monomeric flame retardant additives for polymeric compositions useful in molding, coating and insulating various articles of manufacture.

Brominated biphenol process

Bromobiphenols comprising 2,2' ,6,6'-tetraalkyl-3,3',5,5'-tetrabromo-1,1'-biphenols and derivatives thereof are employed as fire-retardant additives for normally flammable resins yielding fire-retardant polymeric compositions. These fire-retardant compositions are thermally stable and can be molded or formed into fire-retardant articles, such as films, sheeting, fibers, laminates, or reinforced plastics by conventional techniques.

Fire-retardant polymeric compositions containing brominated biphenols

Bromobiphenols containing at least two bromine atoms meta to the phenolic hydroxyl groups can be produced from 3,3',5,5'-tetra-substituted diphenoquinones by reacting the latter with bromine. The reaction can be controlled to produce little, if any, by-product. The products obtained are dependent to some extent on the substituents in the four positions ortho to the hydroxyl groups. The biphenols can be used as antioxidants or as starting materials for preparation of flame-retardent polymeric compositions useful in the molding, coating and insulating arts.

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Schenectady, NY, United States of America

Charles M Orlando