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

Claim 2

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 2 NH--, --NHCO-- and --NHSO 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 1 is hydrogen; alkyl containing 1 to 20 carbon atoms, unsubstituted or substituted with --OH, --SO 3 H, --COOR 8 , --SO 2 NHR 8 , --NHCOR 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 3 H, --COOR 8 , --SO 2 NHR 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 9 ; and --CONHR 9 , said R 8 being hydrogen or alkyl containing 1 to 20 carbon atoms and said R 9 being alkyl containing 1 to 20 carbon atoms; R 2 is hydrogen, alkyl containing 1 to 20 carbon atoms, phenyl or phenyl substituted with alkyl containing up to 20 carbon atoms; R 3 , R 4 , and R 5 each are hydrogen or alkyl containing 1 to 20 carbon atoms and R 4 and R 5 taken together are --CH 2 ) 4 ; R 6 is hydrogen, carboxy, sulfo or alkyl containing 1 to 20 carbon atoms; R 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.

Claim 3

A dye as defined in claim 1 wherein m is 1.

Claim 4

A dye as defined in claim 1 wherein m is 2.

Claim 5

A dye as defined in claim 3 wherein said L' is ##STR59##

Claim 6

A dye as defined in claim 4 wherein said B is alkylsulfonamido and said G is hydrogen.

Claim 7

A dye as defined in claim 3 wherein said L' is ##STR60##

Claim 8

A dye as defined in claim 6 wherein said p is 1.

Claim 9

A dye as defined in claim 7 wherein said A is alkylene.

Claim 10

A dye as defined in claim 8 wherein said E is --CONH--.

Claim 11

A dye as defined in claim 8 wherein said E is --SO 2 NH--.

Claim 12

A dye as defined in claim 7 wherein said A is phenylene.

Claim 13

A dye as defined in claim 11 wherein said E is --SO 2 NH--.

Claim 14

A dye as defined in claim 12 wherein said G is hydroxy.

Claim 15

A dye as defined in claim 1 wherein said Y' is said cyclic moiety (i).

Claim 16

A dye as defined in claim 1 wherein said Y' is said cyclic moiety (ii).

Claim 17

A dye as defined in claim 1 wherein said D' represents the dye radical of an azo dye.

Claim 18

A dye as defined in claim 1 wherein said D' represents the dye radical of a metal-complexed azo dye.

Claim 19

A dye as defined in claim 1 wherein said D' represents the dye radical of a metal-complexed phthalocyanine dye.

Claim 20

A dye as defined in claim 1 wherein said D' represents the dye radical of an azomethine dye.

Claim 21

A dye as defined in claim 1 wherein said D' represents the dye radical of an anthraquinone dye.

Claim 22

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 2 NH--, --NHCO--, and -- --NHSO 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 1 is hydrogen; alkyl containing 1 to 20 carbon atoms, unsubstituted or substituted with --OH, --SO 3 H, --COOR 8 , --SO 2 NHR 8 , --NHCOR 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 3 H, --COOR 8 , --SO 2 NHR 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 9 ; and --CONHR 9 , said R 8 being hydrogen or alkyl containing 1 to 20 carbon atoms and said R 9 being alkyl containing 1 to 20 carbon atoms; R 2 is hydrogen, alkyl containing 1 to 20 carbon atoms, phenyl or phenyl substituted with alkyl containing up to 20 carbon atoms; R 3 , R 4 , and R 5 each are hydrogen or alkyl containing 1 to 20 carbon atoms and R 4 and R 5 taken together are --CH 2 ) 4 , R 6 is hydrogen, carboxy, sulfo or alkyl containing 1 to 20 carbon atoms; R 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.

Claim 23

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 2 NH--, --NHCO--, and -- --NHSO 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 1 is hydrogen; alkyl containing 1 to 20 carbon atoms, unsubstituted or substituted with --OH, --SO 3 H, --COOR 8 , --SO 2 NHR 8 , --NHCOR 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 3 H, --COOR 8 , --SO 2 NHR 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 9 ; and --CONHR 9 , said R 8 being hydrogen or alkyl containing 1 to 20 carbon atoms and said R 9 being alkyl containing 1 to 20 carbon atoms; R 2 is hydrogen, alkyl containing 1 to 20 carbon atoms, phenyl or phenyl substituted with alkyl containing up to 20 carbon atoms; R 3 , R 4 , and R 5 each are hydrogen or alkyl containing 1 to 20 carbon atoms and R 4 and R 5 taken together are --CH 2 ) 4 , R 6 is hydrogen, carboxy, sulfo or alkyl containing 1 to 20 carbon atoms; R 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.

Claim 24

A dye as defined in claim 21 wherein m is 1.

Claim 25

A dye as defined in claim 21 wherein m is 2.

Claim 26

A dye as defined in claim 23 wherein said L' is ##STR64##

Claim 27

A dye as defined in claim 24 wherein said B is alkylsulfonamido and said G is hydrogen.

Claim 28

A dye as defined in claim 23 wherein said L' is ##STR65##

Claim 29

A dye as defined in claim 26 wherein said p is 1.

Claim 30

A dye as defined in claim 27 wherein said A is alkylene.

Claim 31

A dye as defined in claim 28 wherein said E is --CONH--.

Claim 32

A dye as defined in claim 28 wherein said E is --SO 2 NH--.

Claim 33

A dye as defined in claim 27 wherein said A is phenylene.

Claim 34

A dye as defined in claim 31 wherein said E is --SO 2 NH--.

Claim 35

A dye as defined in claim 32 wherein said G is hydroxy.

Claim 36

A dye as defined in claim 21 wherein said Y' is said cyclic moiety (i).

Claim 37

A dye as defined in claim 21 wherein said Y' is said cyclic moiety (ii).

Claim 38

A dye substituted with a group selected from ##STR66## wherein R 1 is hydrogen; alkyl containing 1 to 20 carbon atoms, unsubstituted or substituted with --OH, --SO 3 H, --COOR 8 , --SO 2 NHR 8 , --NHCOR 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 3 H, --COOR 8 , --SO 2 NHR 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 9 ; and --CONHR 9 , said R 8 being hydrogen or alkyl containing 1 to 20 carbon atoms and said R 9 being alkyl containing 1 to 20 carbon atoms; R 2 is hydrogen, alkyl containing 1 to 20 carbon atoms, phenyl or phenyl substituted with alkyl containing up to 20 carbon atoms; R 3 , R 4 , and R 5 each are hydrogen or alkyl containing 1 to 20 carbon atoms and R 4 and R 5 taken together are --CH 2 ) 4 ; R 6 is hydrogen, carboxy, sulfo or alkyl containing 1 to 20 carbon atoms; R 7 is hydrogen, alkyl containing 1 to 20 carbon atoms, carboxy, sulfo or halo; and q is an integer 1 to 4, said groups (i) and (ii) being attached to a carbon atom of said dye and being capable of undergoing cleavage between said S atom and said C atom common to said S and N atoms and between said N atom and said common C atom in the presence of silver ions, soluble silver complex or silver ions and soluble silver complex, said C atom common to said S and N atoms of said groups (i) and (ii) being a tetrahedral carbon atom possessing 4 single covalent bonds.

Claim 39

A dye substituted with a group selected from ##STR66## wherein R 1 is hydrogen; alkyl containing 1 to 20 carbon atoms, unsubstituted or substituted with --OH, --SO 3 H, --COOR 8 , --SO 2 NHR 8 , --NHCOR 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 3 H, --COOR 8 , --SO 2 NHR 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 9 ; and --CONHR 9 , said R 8 being hydrogen or alkyl containing 1 to 20 carbon atoms and said R 9 being alkyl containing 1 to 20 carbon atoms; R 2 is hydrogen, alkyl containing 1 to 20 carbon atoms, phenyl or phenyl substituted with alkyl containing up to 20 carbon atoms; R 3 , R 4 , and R 5 each are hydrogen or alkyl containing 1 to 20 carbon atoms and R 4 and R 5 taken together are --CH 2 ) 4 ; R 6 is hydrogen, carboxy, sulfo or alkyl containing 1 to 20 carbon atoms; R 7 is hydrogen, alkyl containing 1 to 20 carbon atoms, carboxy, sulfo or halo; and q is an integer 1 to 4, said groups (i) and (ii) being attached to a carbon atom of said dye and being capable of undergoing cleavage between said S atom and said C atom common to said S and N atoms and between said N atom and said common C atom in the presence of silver ions, soluble silver complex or silver ions and soluble silver complex, said C atom common to said S and N atoms of said groups (i) and (ii) being a tetrahedral carbon atom possessing 4 single covalent bonds.

Claim 40

A dye as defined in claim 36 wherein R 2 is hydrogen.

Claim 41

A dye as defined in claim 36 wherein R 2 is alkyl.

Claim 42

A dye as defined in claim 36 wherein R 3 and R 4 are alkyl.

Claim 43

A dye as defined in claim 36 wherein R 4 and R 5 are --CH 2 ) 4 .

Claim 44

The compound ##STR67##

Claim 45

The compound ##STR67##

Claim 46

The compound ##STR68##

Claim 47

The compound ##STR68##

Claim 48

The compound ##STR69##

Claim 49

The compound ##STR69##

Claim 50

The compound ##STR70##

Claim 51

The compound ##STR70##

Claim 52

The compound ##STR71##

Claim 53

The compound ##STR71##

Claim 54

The compound ##STR72##

Claim 55

The compound ##STR72##

Claim 56

The compound ##STR73##

Claim 57

The compound ##STR73##

Claim 58

The compound ##STR74##

Claim 59

The compound ##STR74##

Claim 60

The compound ##STR75##

Claim 61

The compound ##STR75##

Claim 62

The compound ##STR76##

Claim 63

The compound ##STR76##