US 4,098,783 A · Dye substituted cyclic 1,3-sulfur-nitrogen compounds as dye image-forming materials in photography

Abstract

This invention relates to color providing compounds useful as dye image-forming materials in color photographic processes. These compounds comprise a complete dye, i.e., a dye radical comprising the chromophoric system of a dye, such as, an azo, anthraquinone, azomethine or phthalocyanine dye and a cyclic moiety capable of undergoing cleavage in the presence of silver ion and/or soluble silver complex containing the group ##STR1## wherein said C atom common to said S and N atoms is a tetrahedral carbon atom possessing 4 single covalent bonds. Preferred compounds comprise the radical of an organic dye substituted with [(L).sub.m-1 -Y] wherein L is a divalent organic linking group containing at least one carbon atom, m is a positive integer 1 or 2, and Y is a cyclic moiety selected from ##STR2## WHEREIN R.sup.1 is hydrogen or a monovalent organic radical; R.sup.2 is hydrogen or a monovalent hydrocarbon radical; and Z represents the carbon atoms necessary to complete a ring system having 4 to 20 atoms, said cyclic moiety (a) being attached to a carbon atom of said dye by a single covalent bond when m is 1 and attached to the carbon atom of said linking group L by a single covalent bond when m is 2 and ##STR3## WHEREIN R.sup.1 and Z have the same meaning given above, said cyclic moiety (b) being attached to a carbon atom of said dye by a spiro union when m is 1 and attached to the carbon atom of said linking group L by a spiro union when m is 2.

Claims50

Dependent claims

A dye substituted with a cyclic moiety containing the group ##STR56## included in the ring and capable of undergoing cleavage between the S atom and the C atom common to the S and N atoms and between the N atom and the common C atom in the presence of silver ions, soluble silver complex or silver ions and soluble silver complex having the formula

D' -- [(L').sub.m-1 Y'].sub.n
wherein D' represents the radical of an organic dye;
m is a positive integer 1 or 2;
n is a positive integer from 1 to 4;
L' represents a divalent organic linking group selected from ##STR57## wherein A and A' each are selected from alkylene containing 1 to 6 carbon atoms, phenylene, phenylenealkylene, alkylenephenylene, phenylenealkylenephenylene and alkylenephenylenealkylene;
B is selected from alkylsulfonamido and alkylcarboxamido wherein said alkyl groups contain 1 to 6 carbon atoms;
E is selected from --CONH--, --SO.sub.2 NH--, --NHCO-- and --NHSO.sub.2 --;
G and G' each is hydrogen or a group selected from amino, hydroxy, carboxy and sulfo;
p is a positive integer 1 or 2;
and Y' is a cyclic moiety selected from ##STR58## wherein R.sup.1 is hydrogen;
alkyl containing 1 to 20 carbon atoms, unsubstituted or substituted with --OH, --SO.sub.3 H, --COOR.sup.8, --SO.sub.2 NHR.sup.8, --NHCOR.sup.9, alkoxy containing 1 to 20 carbon atoms, --N,N-dialkylamino wherein said alkyl groups contain 1 to 20 carbon atoms, phenyl, unsubstituted or substituted with --OH, --SO.sub.3 H, --COOR.sup.8, --SO.sub.2 NHR.sup.8, alkoxy having 1 to 20 carbon atoms, --N,N-dialkylamino wherein said alkyl groups contain 1 to 20 carbon atoms, alkyl containing 1 to 20 carbon atoms and alkenyl containing 1 to 20 carbon atoms;
--COR.sup.9 ;
and --CONHR.sup.9, said R.sup.8 being hydrogen or alkyl containing 1 to 20 carbon atoms and said R.sup.9 being alkyl containing 1 to 20 carbon atoms;
R.sup.2 is hydrogen, alkyl containing 1 to 20 carbon atoms, phenyl or phenyl substituted with alkyl containing up to 20 carbon atoms;
R.sup.3, R.sup.4, and R.sup.5 each are hydrogen or alkyl containing 1 to 20 carbon atoms and R.sup.4 and R.sup.5 taken together are --CH.sub.2).sub.4 ;
R.sup.6 is hydrogen, carboxy, sulfo or alkyl containing 1 to 20 carbon atoms;
R.sup.7 is hydrogen, alkyl containing 1 to 20 carbon atoms, carboxy, sulfo or halo selected from chloro and bromo;
and q is an integer 1 to 4, said cyclic moiety being attached to an aromatic nuclear carbon atom of said D' by a single covalent bond when m is 1 and being attached to a carbon atom of said A of said divalent organic linking group by a single covalent bond when m is 2 and said C atom common to said S and N atoms of said cyclic moiety being a tetrahedral carbon atom possessing 4 single covalent bonds.

15 more elements

An azo dye substituted with a cyclic moiety containing the group ##STR61## included in the ring and capable of undergoing cleavage between the S atom and the C atom common to the S and N atoms and between the N atom and the common C atom in the presence of silver ions, soluble silver complex or silver ions and soluble silver complex having the formula

D'--.[(L').sub.m-1 Y'].sub.n
wherein D' represents the radical of an azo dye;
m is a positive integer 1 or 2;
n is a positive integer 1 or 2;
L' represents a divalent organic linking group selected from ##STR62## wherein A and A' each are selected from the alkylene containing 1 to 6 carbon atoms, phenylene, phenylenealkylene, alkylenephenylene, phenylenealkylenephenylene and alkylphenylenealkylene;
B is selected from alkylsulfonamido and alkylcarboxamido wherein said alkyl groups contain 1 to 6 carbon atoms;
E is selected from --CONH--, --SO.sub.2 NH--, --NHCO--, and -- --NHSO.sub.2 --;
G and G' each is hydrogen or a group selected from amino, hydroxy, carboxy, and sulfo;
p is a positive integer 1 or 2;
and Y' is a cyclic moiety selected from ##STR63## wherein R.sup.1 is hydrogen;
alkyl containing 1 to 20 carbon atoms, unsubstituted or substituted with --OH, --SO.sub.3 H, --COOR.sup.8, --SO.sub.2 NHR.sup.8, --NHCOR.sup.9, alkoxy containing 1 to 20 carbon atoms, --N,N-dialkylamino wherein said alkyl groups contain 1 to 20 carbon atoms;
phenyl, unsubstituted or substituted with -OH, --SO.sub.3 H, --COOR.sup.8, --SO.sub.2 NHR.sup.8, alkoxy having 1 to 20 carbon atoms, --N,N-dialkylamino wherein the alkyl groups contain 1 to 20 carbon atoms, alkyl containing 1 to 20 carbon atoms and alkenyl containing 1 to 20 carbon atoms;
--COR.sup.9 ;
and --CONHR.sup.9, said R.sup.8 being hydrogen or alkyl containing 1 to 20 carbon atoms and said R.sup.9 being alkyl containing 1 to 20 carbon atoms;
R.sup.2 is hydrogen, alkyl containing 1 to 20 carbon atoms, phenyl or phenyl substituted with alkyl containing up to 20 carbon atoms;
R.sup.3, R.sup.4, and R.sup.5 each are hydrogen or alkyl containing 1 to 20 carbon atoms and R.sup.4 and R.sup.5 taken together are --CH.sub.2).sub.4, R.sup.6 is hydrogen, carboxy, sulfo or alkyl containing 1 to 20 carbon atoms;
R.sup.7 is hydrogen, alkyl containing 1 to 20 carbon atoms, carboxy, sulfo or halo selected from chloro and bromo;
and q is an integer 1 to 4, said cyclic moiety being attached to an aromatic nuclear carbon atoms of said D' by a single covalent bond when m is 1 and being attached to a carbon atom of said A of said divalent organic linking group by a single covalent bond when m is 2, and said C atom common to said S and N atoms of said cyclic moiety being a tetrahedral carbon atom possessing 4 single covalent bonds.

15 more elements

Dependencies are inferred from the claim text.

Dye substituted cyclic 1,3-sulfur-nitrogen compounds as dye image-forming materials in photography

Life of this patent

Dye substituted cyclic 1,3-sulfur-nitrogen compounds as dye image-forming materials in photography

Life of this patent

Abstract

Claims50