Gulf Research & Development Company

Gulf Oil Corporation

Gulf Research & Development

Walter P Barie, Jr

Johann G Schulz

Edward T Sabourin

James T Eurich

Anatoli Onopchenko

Kiran R Bakshi

Norman W Franke

Pallavoor R Lakshmanan

Thomas F Huemmer

A one-step solution technique for preparing an aromatic polyimide acid which comprises reacting an aromatic dianhydride with an aromatic diamine in the presence of diglyme and a sufficient amount of a co-solvent to maintain the polyimide acid in solution, said co-solvent having the formula:

Method of preparation of polyimide acids

A one-step solution technique for preparing an aromatic polyimide acid which comprises reacting an aromatic dianhydride with an aromatic diamine in the presence of propylene glycol methyl ether.

Preparation of an aromatic polyimide acid by solution polymerization

Novel resin products produced by reacting unique polycyclic, aromatic, polycarboxylic acid products with low molecular weight polyols display satisfactory toughness properties and good Barcol hardness values. The process for preparing these novel resin products first involves preparing an intimate, finely divided mixture comprising the acid product derived from the nitric acid oxidation of naturally occurring solid carbonaceous material, a roughly equivalent amount of a liquid polyol, and a suitable acid catalyst. The mixture is then subjected to a precure step which involves heating at temperatures between 80.degree. and 150.degree. C. for from about fifteen minutes to about four hours. The precured mixture may thereafter be subjected to suitable molding conditions at a temperature below about 220.degree. C.

Molded resin product and process for producing same

Coating compositions are provided which consist of a polymerizable ethylenically unsaturated material having included therein as a photoinitiator a di- or tetraester of 3,4,3',4'-benzophenone tetracarboxylic acid or a diester of 4,4'-benzophenone dicarboxylic acid.

Photopolymerizable compositions

Novel, 1,2-Epoxy Resin products using unique polycyclic, aromatic, polycarboxylic acid products as crosslinking agents display satisfactory electrical properties and good Barcol hardness values. The process for preparing these novel resin products involves admixing: a 1,2-epoxy resin containing on the average more than one 1,2-epoxy groups per molecule and the acid product derived from the nitric acid oxidation of naturally occurring solid carbonaceous material along with a suitable accelerator. The mixture is then subjected to a precure step which involves heating at temperatures between 50.degree. and 150.degree. C. for from about five minutes to about six hours. The mixture is thereafter subjected to suitable molding conditions.

Molded epoxy resin product containing acids from oxidation of

A new composition capable of being cured to a solid resin highly resistant to boiling acetone which comprises: (a) a 1,2-epoxy resin containing on the average more than one 1,2-epoxy group per molecule; (b) a residue remaining from the process wherein cumene (C) is reacted with maleic anhydride (MA) in the presence of (that is, in contact with) zinc chloride to obtain a reaction product containing dimethylbenzyl succinic anhydride (DMBSA), 5-phenyl-5-methylhexane-1,2,3,4-tetracarboxylic acid dianhydride (PMTD) and addition products of C and MA containing more than two anhydride groups per molecule (AP) and wherein a sufficient amount of said DMBSA is removed from said reaction product to give a residue containing a maximum of 25 weight percent DMBSA; and (c) an accelerator.

Epoxy resin compositions (case B) containing cumene-maleic anhydride

A new composition capable of being cured to a solid resin highly resistant to boiling acetone which comprises: (a) a 1,2-epoxy resin containing on the average more than one 1,2-epoxy group per molecule; (b) a residue remaining from the process wherein cumene (C) is reacted with maleic anhydride (MA) to obtain a reaction product containing dimethylbenzyl succinic anhydride (DMBSA), 5-phenyl-5-methylhexane-1,2,3,4-tetracarboxylic acid dianhydride (PMTD) and addition products of C and MA containing more than two anhydride groups per molecule (AP) and wherein a sufficient amount of said DMBSA is removed from said reaction product to give a residue containing a maximum of 25 weight percent DMBSA; and (c) an accelerator.

Epoxy resin compositions (Case A) containing cumene-maleic anhydride

A stable diaryl dianhydride-epoxy resin solution for preparing handleable, formable resin-impregnated reinforcing material and fully cured laminates. A non-viscous solution of 3,4,3',4'-benzophenone tetracarboxylic dianhydride and the reaction product of epichlorohydrin and bisphenol A is obtained in acetone.

Polyepoxy resin-diaryl dianhydride laminating resins and laminates

A clear, colorless cured resin is prepared from a solid epoxy resin and 5-phenyl-5-methylhexane-1,2,3,4-tetracarboxylic acid dianhydride.

Clear and colorless epoxide dianhydride cured resins

An improved method is described for the preparation of certain acetylene-substituted polyimide oligomers which are substantially free of reaction solvent and thus do not fracture at use temperatures above 600.degree. F. (316.degree. C.). The acetylene-substituted polyimide oligomers are prepared by reacting an aromatic tetracarboxylic acid dianhydride such as benzophenone tetracarboxylic acid dianhydride with an aromatic diamino compound such as a diamino polyarylene ether in the presence of N-methyl-2-pyrrolidone (NMP) as a solvent to form a first reaction product which is in turn reacted with an aminoarylacetylene to form a solution of an acetylene-substituted polyamic acid oligomer in NMP. The polyamic acid oligomer is thereafter converted to the desired acetylene-terminated polyimide oligomer by heating in the continued presence of said N-methyl-2-pyrrolidone. The N-methyl-2-pyrrolidone can then be removed by any suitable means such as by precipitation of the acetylene-substituted polyimide oligomer in a non-solvent such as ethanol.

Preparation of acetylene-substituted polyimide oligomers and polyimide

A stable impregnating solution of 3,3',4,4'-benzhydrol tetracarboxylic dianhydride and a polyepoxide for preparing handleable, formable resin-impregnated reinforcing material and fully cured laminates. A substantially non-reacted solution of 3,3',4,4'-benzhydrol tetracarboxylic dianhydride and a diglycidyl ether of bisphenol A is obtained in acetone.

Polyepoxy-3,3',4,4'-benzhydrol tetracarboxylic dianhydride laminating

A new epoxy resin adhesive composition having high tensile lap shear and T-peel strengths. The composition contains a nitrile rubber-modified epoxy resin, certain solid biphenyl anhydrides having one anhydride function on each phenyl group, and a powdered metal.

Adhesive compositions

A novel polyamic acid intermediate composition in a polar, aprotic solvent and the corresponding fully condensed polyimide are prepared from 3,3',4,4'-benzhydrol tetracarboxylic dianhydride and a diamine having at least two carbon atoms such as bis(4-aminophenyl)ether.

Polyamic-acids prepared from 3,3,4,4-benzhydrol tetracarboxylic

A new epoxy resin adhesive composition having exceptionally high tensile lap shear strength is prepared from a mixture of a polyglycidyl ether of a novolac resin, a diglycidyl ether of bisphenol A, 3,4,3',4'-benzophenone tetracarboxylic dianhydride and maleic anhydride. The resin is cured with a metal complex of acetylacetone such as zinc acetylacetonate.

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Glenshaw, PA, United States of America

Walter P Barie, Jr