Occidental Chemical Corporation

Hooker Chemicals & Plastics Corporation

Willis T Schwartz

Jeffrey S Stults

Raymond R Hindersinn

Edwin Dorfman

Frank J Dinan

Joseph A Pawlak

Rudolph F Mundhenke

John R Molinaro

Timothy A Meterko

Gideon Salee

Daniel J Scharf

Mary K Cocoman

Charles S Ilardo

Roger A Wolfe

Crude mixtures of dioxydiphthalic anhydride containing alkali metal salts are purified by treating the crude mixture with an alkanol, such as n-butanol, to form the dioxydiphthalic acid diester; removing the insoluble alkali metal salts by filtration; removing the excess alkanol; and reconverting the dioxydiphthalic acid diester to dioxydiphthalic anhydride.

Method for the purification of dioxydiphthalic anhydride and ester

This invention relates to novel fluorinated bis-imides of the formula ##STR1## where X is H or F. The compounds are useful as additives to enhance the properties of high performance polymers such as polyimides.

Highly fluorinated bis-imides

Bis-imides of dioxydiphthalic or oxydiphthalic anhydride, are characterized by the formula ##STR1## where Z is H, alkyl of 1-12 carbon atoms, or ##STR2## A is H, Cl, F, NO.sub.2, OH, CF.sub.3, alkyl, alkoxy, alkylaryl or aryloxy, wherein the alkyl groups are 1-6 carbon atoms and the aryl groups are 6-14 carbon atoms; alkenyl or alkynyl of 2-6 carbon atoms; or benzoyl; and Y is H, Cl, F, NO.sub.2, OH, or CF.sub.3 ; X is halogen; X' is hydrogen or halogen; or X and X' together represent an oxygen atom, forming a second ether linkage.

Bis-imides of dioxydiphthalic acid

Polyimide copolymers are disclosed having the recurring structure ##STR1## wherein AR is AR.sub.1 or AR.sub.2, wherein AR.sub.1 is ##STR2## and wherein AR.sub.2 is ##STR3## provided that the molar ratio of AR.sub.1 to AR.sub.2 is 3:1 to 1:3, and wherein AR.sub.3 is ##STR4## These polyimides have unexpected properties which are useful in various electronic applications.

Copolyimide ODPA/BPDA/4,4'-ODA or P-PDA

Oxydiphthalic acid esters of the formula ##STR1## where Z is H or alkyl, and X is halo, X' is H or halo, or X and X' together represent an oxygen atom; are prepared by the esterification reaction of the corresponding halo-oxydiphthalic anhydride or dioxydiphthalic anhydride with an alkanol.

Dioxydiphthalic acid esters

Novel halogenated polyimides and co-polyimides comprise recurring imide structural units of the formula ##STR1## where X is F, Cl, Br or I; Y is H, F, Cl, Br or I; and R is a divalent organic radical.

Polyimides and copolyimides based on halo-oxydiphthalic anhydrides

Dioxydiphthalic anhydride is prepared by the reaction of dihalophthalic anhydride with an alkali metal compound, such as potassium carbonate. The compound is particularly useful as a monomer in the preparation of polyimides.

Dioxydiphthalic anhydride

A co-polyimide based upon a mixture of 4,4'-oxydiphthalic dianhydride (ODPA) and 3,4,3',4'-biphenyltetracarboxylic dianhydride (BPDA) as the dianhydride component and either 4,4'-oxydianiline (ODA) or paraphenylene diamine as the amine component is disclosed. The molar ratio between the ODPA and BPDA ranges from 3:1 to 1:3. The co-polyimide may either be formed as a random copolymer, or as a block copolymer where the blocks are based upon blocks of polymer containing ODPA and blocks of polymer containing BPDA provided that the molar ratios of ODPA and BPDA are in the ratio of 3:1 to 1:3.

Oxydiphthalic anhydrides of the formula ##STR1## are prepared by reacting a halophthalic anhydride with potassium carbonate in:

Process for the preparation and recovery of oxydiphthalic anhydrides

Novel polyimides and co-polyimides are prepared by the condensation polymerization of an aryl diamine with dioxydiphthalic anhydride or a mixture thereof with oxydiphthalic anhydride. The polyimides and co-polyimides prepared exhibit a low moisture absorption and improved dielectric properties and can be tailored to provide a composition having desirable mechanical properties, specifically, rigidity.

Polyimides and co-polyimides based on dioxydiphthalic anhydride

Process of preparing dioxydiphthalic anhydride

A process for the production of 4-bromophthalic anhydride which comprises the reaction of 4-chlorotetrahydrophthalic anhydride with elemental bromine, in the presence of a catalytically effective amount of iron or an iron salt is disclosed.

Process for the preparation of 4-bromophthalic anhydride

Phenoxy phthalic anhydrides are prepared by the reaction of a fluorophthalic anhydride with a phenol compound in the presence of potassium fluoride and a polar, aprotic solvent.

Phenoxy phthalic anhydrides

Novel halo-oxydiphthalic anhydrides are of the formula ##STR1## where X is F, Cl, Br, or I; X' is H, F, Cl, Br, or I.

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Grand Island, NY, United States of America

Willis T Schwartz