Polaroid Corporation

Eva R Karger

James R Bartels-Keith

Paul T MacGregor

Jean B Rogers

This invention relates to amino hydroxy cyclohexenones of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each are alkyl, usually containing 1 to 20 carbon atoms. In another embodiment, the present invention is directed to the use of the above-denoted compounds as photographic silver halide developing agents and to photographic processes, products and compositions employing the same.

Amino hydroxy cyclohexenone developing agents

The present invention relates to novel bicyclic compounds useful as photographic silver halide developing agents, to the preparation of these compounds and to photographic products, processes and compositions employing the same. The subject compounds may be represented by the formula ##STR1## wherein R.sub.1 and R.sub.2, the same or different, each represents hydrogen, a hydrocarbon moiety, preferably an alkyl group, --COOH or --COOR.sup.1 wherein R.sup.1 is an alkyl group; R.sub.3 and R.sub.4, the same or different, each represent hydrogen or an alkyl group, R.sub.5 represents hydrogen or --COR.sup.2 wherein R.sup.2 is an alkyl group; R.sub.6 represents hydrogen when R.sub.5 is hydrogen and represents hydrogen or --OCOR.sup.3 wherein R.sup.3 is an alkyl group the same as R.sup.2 when R.sub.5 represents --COR.sup.2 ; X represents --OH, --NH.sub.2 or --NHCOR.sup.4 wherein R.sup.4 represents an alkyl group the same as R.sup.2 ; Y represents --OH or --OCOR.sup.5 wherein R.sup.5 represents an alkyl group the same as R.sup.2 ; and Z represents .dbd.O or .dbd.NCOR.sup.6 wherein R.sup.6 is an alkyl group the same as R.sup.2.

Bicyclic reductone developing agents

This invention relates to a method of synthesizing 3-amino-2-hydroxy-2-cyclopentenones possessing an aliphatic substituent in the 4-position which comprises reacting cyanoacetamide with an aliphatic aldehyde to yield the corresponding .beta.-substituted-.alpha.,.alpha.'-dicyanoglutaramide, hydrolyzing the amide to the corresponding .beta.-substituted glutaric acid, esterifying the acid to the corresponding dialkyl diester, converting the diester to a 1,2-bis(trimethylsiloxy)-4-substituted cyclopentene by reductive cyclization using chlorotrimethylsilane in the presence of sodium, hydrolyzing and oxidizing the bis(trimethylsiloxy) compound to the 2-hydroxy-4-substituted-2-cyclopentenone in the presence of a cupric salt, nitrosating the 2-cyclopentenone to the 2-hydroxy-4-substituted-5-oximino-2-cyclopentenone, converting the oxime to the 2-acetoxy-3-amino-4-substituted-2-cyclopentenone by reductive acetylation and removing the acetyl group by alkanolysis to yield the 3-amino-2-hydroxy-4-substituted-2-cyclopentenone product.

Synthesis of amino hydroxy cyclopentenones

This invention relates to derivatives of phthalaldehydic and naphthalaldehydic acid useful as intermediates in the preparation of pH-sensitive phthalide and naphthalide indicator dyes. A class of intermediates provided by the present invention comprises compounds of the formula: ##STR1## wherein A represents 4'-hydroxy-1'-naphthyl; B represents 4'-hydroxy-1'-naphthyl or indol-3-yl and C represents a 2-carboxy-1-phenyl radical or an 8-carboxy-1-naphthyl radical and preferably is 8-carboxy-1-naphthyl.

1:1 Adducts of indole and (na)phthalaldehydic acid

Trinapthylmethane compounds

This invention relates to a class of indicator dyes useful as optical filter agents in photographic processes to protect a selectively exposed photosensitive material from further exposure during processing in the presence of incident light. Such dyes comprise 3,3-disubstituted phthalides and 3,3-disubstituted naphthalides wherein one of the 3,3-substituents is an indol-3-yl radical substituted with hydrogen on the heterocyclic N atom and the other of said 3,3 substituents is a p-hydroxycarbocyclic aryl radical selected from a 4'-hydroxy-1'-phenyl radical and a 4'-hydroxy-1'-naphthyl radical.

3,3-Disubstituted phthalides and naphthalides

This invention relates to derivatives of phthalaldehydic and naphthalaldehydic acid useful as intermediates in the preparation of pH-sensitive phthalide and naphthalide indicator dyes. One class of intermediates provided by the present invention comprises compounds of the formula: ##SPC1## Wherein A represents 4'-hydroxy-1'-naphthyl and X represents the atoms necessary to complete a ring-closing moiety selected from a phthalide and a naphthalide and preferably is naphthalide. Another class of intermediates provided by the present invention comprises compounds of the formula: ##SPC2## Wherein A represents 4'-hydroxy-1'-naphthyl; B represents 4'-hydroxy-1'-naphthyl or indol-3-yl and C represents a 2-carboxy-1-phenyl radical or an 8-carboxy-1-naphthyl radical and preferably is 8-carboxy-1-naphthyl.

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Arlington, MA, United States of America

Eva R Karger