Diels-Alder adducts of hexahalocyclopentadiene and dialkyl-alphamethylstyrene

Abstract

New chemical compounds useful as intermediates are 5-(1-methyl-3,4,5,6,7,7-hexahalo-norborn-4-ene-1)-isophthalic acid and 4-(1-methyl 3,4,5,6,7,7-hexahalo-norborn-4-ene-1)-orthophthalic acid, formed by oxidation of the primary or secondary alkyl groups containing from one to ten carbon atoms on the benzene ring of the Diels-Alder adduct of equimolecular amounts of hexahalocyclopentadiene and either 3,5-dialkyl-.alpha.-methyl-styrene and 3,4-dialkyl-.alpha.-methylstyrene. The acyl derivatives of these intermediates do not burn or support combustion and are also useful as extreme-pressure additives in lubricating oils. The following acyl derivatives of 5-(1-methyl-3,4,5,6,7,7-hexachloro-norborn-4-ene-1)-isophthalic acid have been prepared: the dichloride, diamide, dianilide, diethylester, polyphenylester, poly(chlorophenyl) ester, poly-ethylene glycol ester, diphenylthioester, di-methallylester, and unsaturated polyester. Also, the co-polyphenylesters of 5-(1-methyl-3,4,5,6,7,7-hexachloro-norborn-4-ene-1)-isophthalic acid and terephthalic or adipic acid; the polyamide of 5-(1-methyl-3,4,5,6,7,7-hexachloro-norborn-4-ene-1)-isophthalic acid and 1,6-hexanediamine; the copolyamides of 5-(1-methyl-3,4,5,6,7,7-hexachloronorborn-4-ene-1) isophthalic acid and 1,6-hexanediamine and terephthalic acid or adipic acid; the co-polyethylene glycol ester of 5-(1-methyl-3,4,5,6,7,7-hexachloro-norborn-4-ene-1) isophthalic acid and terephthalic acid; and a phosphorus adduct of 5-(1-methyl-3,4,5,6,7,7-hexachloro-norborn-4-ene-1) have been prepared.

Dependencies are inferred from the claim text.