Polyphenylcarboxylic acid adamantane compounds and polymers prepared therefrom
AssigneeStandard Oil Company (Indiana)
InventorsAllen I. Feinstein, Ellis K. Fields
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Abstract
Adamantane compounds having 2 to 4 bridgehead positions substituted with phenylacyl moieties are prepared by oxidizing poly(phenylalkyl) adamantanes. The polyacyl adamantane compounds are useful as intermediates for polyesters, polyamides and polyimides. The esters are useful as plasticizers for polyvinylchloride.
Claims27
A polyphenylcarboxylic acid adamantane compound of the general formula ##STR10## wherein R.sub.1 is selected from the group consisting of ##STR11## R.sub.2 and R.sub.3 are individually selected from the group consisting of hydrogen, an alkyl radical of 1 to 4 carbon atoms, a phenyl radical, a biphenyl radical, and a naphthyl radical, R.sub.4 is hydrogen or an alkyl group of 1 to 24 carbon atoms.
A process for preparing adamantane polyphenylcarboxylic acid compounds, wherein the carboxy groups are in the 3, 4, 5 positions on the phenyl rings which comprises oxidizing the reaction product of a polybromoadamantane and an alkyl benzene in a liquid phase oxidation at a temperature within the range of about 75.degree. to 300.degree. C., the oxidizing agent being selected from the group consisting of sodium dichromate, potassium dichromate, ammonium dichromate, and molecular oxygen.
A resinous polymer consisting essentially of recurring units of a polyacyl radical of an adamantane polyphenylcarboxylic acid wherein the said resinous polymer is of the structural formula:
- ##STR12## wherein X and Y are selected from the group consisting of ##STR13## and -H, n is a whole number of 1 to 4, L is selected from the group consisting of ##STR14## and --O-- radicals, Z is selected from the group consisting of aliphatic moieties of 2 to 20 carbon atoms and aromatic moieties selected from the group consisting of one benzene ring and the condensed rings of naphthylene, phenanthrylene and anthrylene, m is a number of said recurring units wherein the said resinous polymer has an inherent viscosity of at least 0.20 dl/g in a 60/40 phenol-tetrachloroethane solvent at 30.degree. C.
Dependencies are inferred from the claim text.