Amoco Corporation

Neal R Nowicki

Douglas E Fjare

David J Fenoglio

Edwin F Morello

John L Melquist

David E James

Allyson J Beuhler

Donald E Thomka

James D Lowry, Jr

Wayne P Schammel

Juergen K Holzhauer

Walter Partenheimer

Weilong L Chiang

Robert W McCoy

A group of polyimides and copolyimides made from 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA) or 2,2-bis(3,4-dicarboxyphenyl)propane dianhydride (IPAN) their acid or ester forms and selected aromatic diamines are disclosed which are useful for substrate coatings and interlevel dielectrics in on-chip and multi-chip package applications. In such applications these polymers exhibit lower dielectric constant, lower moisture uptake and reduced dielectric constant variation with temperature and humidity than existing polymers, yet they are both thermally stable at required processing temperatures and can form suitably adherent, pinhole-free coatings on electronic component substrates.

Low dielectric constant, low moisture uptake polyimides and copolyimides

A group of polyimides and copolyimides made from 6FDA, IPAN, or their acid or ester forms, and selected aromatic diamines are disclosed which are useful for substrate coatings and interlevel dielectrics in on-chip and multi-chip package applications. In such applications these polymers exhibit lower dielectric constant, lower moisture uptake and reduced dielectric constant variation with temperature and humidity than existing polymers, yet they are both thermally stable at required processing temperatures and can form suitably adherent, pinhole-free coatings on electronic component substrates.

Polyimides useful in multilayer electronic devices containing the 4,4'-bis(4-amino-2-trifluoromethylphenoxy) biphenyl moiety have low dielectric constants, low moisture uptake, high thermal degradation stability, low glass transition temperature.

Polyimide containing 4,4'-bis(4-amino-2-trifluoromethylphenoxy)-biphenyl

Resinous condensation polymers of polycarboxylic acid compounds and aromatic diprimary amines comprising diamino-t-butylbenzenes are described. In particular, film-forming polyamides, polyimides and polyamide-imides and their copolymers made using diamino-t-butylbenzenes which have amino groups meta or para to each other on a benzene ring are described. These polymers have some solubility in organic solvents such as N-methylpyrrolidone, a high glass transition temperature, excellent thermal stability, and are useful in films, fibers and composites, and in the electronics industry as electrical component substrates, protective coatings, interlevel dielectrics and the like.

Polyamide, polyimide, and polyamide-imide polymers of

Soluble, film-forming, polyamides, polyimides, and polyamide-imides and their copolymers made using 3,5-diamino-t-butylbenzene are described. These polymers have some solubility in organic solvents such as N-methylpyrrolidone, a high Tg, excellent thermal stability, lower density and lower moisture uptake and are useful in films, fibers and composites, and in the electronics industry as electrical component substrates, protective coatings, interlevel dielectrics and the like.

Polyamide, polyimide, and polyamide-imide polymers and copolymers using

Resinous condensation polymers of polycarboxylic acid compounds and aromatic diprimary amines comprising diamino-t-butylbenzenes are described. In particular, film-forming polyamides, polyimides and polyamide-imides and their copolymers made using diamono-t-butylbenzenes which have amino groups meta or para to each other on a benzene ring are described. These polymers have some solubility in organic solvents such as N-methylpyrrolidone, a high glass transition temperature, excellent thermal stability, and are useful in films, fibers and composites, and in the electronics industry as electrical component substrates, protective coatings, interlevel dielectrics and the like.

Polyamide from diamino-t-butylbenzene

Resinous condensation polymers of polycarboxylic acid compounds and aromatic diprimary amines comprising diamino-t-butylbenzens are described. In particular, film-forming polyamides, polyimides and polyamide-imides and their copolymers made using diamino-t-butylbenzenes which have amino groups meta or para to each other on a benzene ring are described. These polymers have some solubility in organic solvents such as N-methylpyrrolidone, a high glass transition temperature, excellent thermal stability, and are useful in films, fibers and composites, and in the electronics industry as electrical component substrates, protective coatings, interlevel dielectrics and the like.

Polyamide from 3,5-diamino-t-butylbenzene

Improved acid yield and product quality are realized in the oxidation of aromatic hydrocarbons in a two-stage process, employing an aqueous solvent system and an increased proportion of bromine, and, optionally, of catalytic metals, in the second stage.

Staged aromatics oxidation in aqueous systems

A method is disclosed for the liquid-phase oxidation of pseudocumene in the presence of an oxidation catalyst comprising cobalt, manganese, and bromine components wherein the metal catalyst are recycled to the oxidation reactor in the form of their oxalates.

Batch or semicontinuous pseudocumene oxidation and catalyst recovery and

Partially soluble, film-forming polyimides and their copolymers made using 3,5-diaminobenzotrifluoride are described. Thin films and coatings of these materials are relatively colorless and the polymers have a high Tg, excellent thermal stability, lower moisture uptake, and lower dielectric constant. They are useful as films, fibers, molded articles and as protective coatings, interlevel dielectrics, electric circuit substrates and the like for the electronics industry.

Polyimide polymers and copolymers using 3,5-diaminobenzotrifluoride

A process is disclosed for producing cyclized aromatic compounds by the liquid-phase air oxidation of 2-methyl-substituted biphenyls and diphenylmethanes in an acetic acid medium in the presence of a cobalt-manganese-bromine catalyst or a zirconium-cobalt-manganese-bromine catalyst wherein the mole ratio of cobalt-to-manganese is about 1.0:0.1 to about 1.0:10.0 and the ratio of zirconium-to-cobalt is about 0.005:1.0 to about 0.20:1.0, and mole ratio of bromine to total metals of said cobalt-manganese-bromine catalyst or zirconium-cobalt-manganese-bromine catalyst is from about 0.2:1.0 to about 20.0:1.0, which process comprises conducting the reaction in a batch process at a temperature of from 75.degree. C. to about 250.degree. C. at a pressure of from 1 to 100 atmospheres, or continuously in two stages comprising a first-stage reaction at a temperature of about 75.degree. C. to about 200.degree. C. and a second-stage reaction at a temperature of about 150.degree. C. to about 250.degree. C. and recycling the cobalt-manganese catalyst or the zircnium-cobalt-manganese catalyst by oxalate precipitation of the catalyst at temperatures of about 110.degree. C. to about 200.degree. C. prior to the separation of mother liquor and using about 0.25 to about 2.5 moles of oxalic acid per mole of cobalt and manganese or mole of zirconium-cobalt-manganese and continuously recycling the recovered catalyst metals to the oxidation stages. The products of this novel process, anthraquinones and fluorenones, are useful for the manufacture of dyestuffs and pharmaceuticals.

Process for preparation of anthraquinones and fluorenones

A continuous process is disclosed for producing trimellitic acid by the liquid-phase air oxidation of pseudocumene in an acetic acid medium in the presence of a cobalt-manganese-bromine catalyst or a zirconium-cobalt-manganese-bromine catalyst wherein the mole ratio of cobalt-to-manganese is about 1.0:0.1 to about 1:5 and the ratio of zirconium-to-cobalt is about 0.005:1 to about 0.20:1, and mole ratio of bromine to total metals of said cobalt-manganese-bromine catalyst or zirconium-cobalt-manganese-bromine catalyst is from about 0.2:1.0 to about 2.0:1.0, which process comprises conducting the reaction continuously in two stages comprising a first-stage reaction at a temperature of about 250.degree. F. to about 350.degree. F. and a second-stage reaction at a temperature of about 350.degree. F. to about 450.degree. F. and recycling the cobalt-manganese catalyst or the zirconium-cobalt-manganese catalyst by oxalate precipitation of the catalyst at temperatures of about 250.degree. F. to about 375.degree. F. prior to the separation of mother liquor and using about 0.25 to about 2.5 moles of oxalic acid per mole of cobalt and manganese or mole of zirconium-cobalt-manganese and continuously recycling the recovered catalyst metals to the first-stage oxidation. The product of this novel process, trimellitic acid, is useful for the manufacture of polyamide-imides which are used as fibers or molded articles, including automotive parts.

Process for the manufacture of trimellitic acid

A process is disclosed for producing cyclized aromatic compounds by the liquid-phase air oxidation of 2-methyl-substituted biphenyls and diphenylmethanes in an acetic acid medium in the presence of a cobalt-manganese-bromine catalyst or a zirconium-cobalt-manganese-bromine catalyst wherein the mole ratio of cobalt-to-manganese is about 1.0:0.1 to about 1.0:10.0 and the ratio of zirconium-to-cobalt is about 0.005:1.0 to about 0.20:1.0, and mole ratio of bromine to total metals of said cobalt-manganese-bromine catalyst or zirconium-cobalt-manganese-bromine catalyst is from about 0.2:1.0 to about 20.0:1.0, which process comprises conducting the reaction in a batch process at a temperature of from 75.degree. C. to about 250.degree. C. at a pressure of from 1 to 100 atmospheres, or continuously in two stages comprising a first-stage reaction at a temperature of about 75.degree. C. to about 200.degree. C. and a second-stage reaction at a temperature of about 150.degree. C. to about 250.degree. C. and recycling the cobalt-manganese catalyst or the zirconium-cobalt-manganese catalyst by oxalate precipitation of the catalyst at temperatures of about 110.degree. C. to about 200.degree. C. prior to the separation of mother liquor and using about 0.25 to about 2.5 moles of oxalic acid per mole of cobalt and manganese or mole of zirconium-cobalt-manganese and continuously recycling the recovered catalyst metals to the oxidation stages. The products of this novel process, anthraquinones and fluorenones, are useful for the manufacture of dyestuffs and pharmaceuticals.

A method is disclosed for recovery and recycle of metal catalyst components of a catalyst from the liquid-phase oxidation of pseudocumene in the presence of an oxidation catalyst comprising cobalt, manganese, and bromine components or cobalt, manganese, zirconium and bromine components wherein said catalyst components are recovered by oxalate precipitation from aqueous residue.

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St. Charles, IL, United States of America

Neal R Nowicki