# US 5,702,866 A · Dihydrazides > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,702,866 A - Document ID: US5702866A - Status: Granted - Kind: A - Application number: 08/736,599 - Filed: 1996-10-24 - Granted: 1997-12-30 - Earliest claimed: 1994-05-24 - Assignees: Ilford Limited - Inventors: Mario Fryberg; Otto Gottel; Thomas Stauner - Web page: https://patentgrep.com/patent/US5702866A ## CPC - C07C 243/38: with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings - C07C 323/37: the sulfur atom of the sulfide group being further bound to a carbon atom of a six-membered aromatic ring - C07D 213/22: containing two or more pyridine rings directly linked together, e.g. bipyridyl - C07D 213/68: attached in position 4 - C07D 213/70: Sulfur atoms - C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms - C07D 233/56: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms - C07D 235/08: Radicals containing only hydrogen and carbon atoms - C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles - C07D 295/15: to an acyclic saturated chain - G03C 1/061: {Hydrazine compounds} - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - G03C: PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES (for photomechanical purposes G03F); PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY (photographic processes characterised by the use or manipulation of apparatus classifiable per se in subclass G03B, see G03B; photomechanical production of textured or patterned surfaces G03F; electrophotography, magnetography G03G) ## Abstract This subject invention relates to novel dihydrazide compounds useful as dot-promoting agents in photographic image systems, methods for making them, and to photographic materials which comprise these compounds. ## Claims ### Claim 1 A photographic silver halide material which comprises at least one silver halide emulsion layer, wherein at least one layer of said material comprises at least one hydrazide having the general formula: B--(A.sup.+)--C (G.sup.-) where B and C are the same or different and have formula I: ##STR69## where R.sub.1 is hydrogen, alkyl, alkoxy or a blocking group selected from the group consisting of ##STR70## wherein R.sub.5 and R.sub.6 each are independently selected from the group consisting of hydrogen, alkyl, aminoalkyl, alkylaminoalkyl, acylaminoalkyl, alkylsulphonylaminoalkyl, arylsulphonylaminoalkyl, trialkylammoniumalkyl, hydroxyalkyl, haloalkyl, cycloalkyl, alkoxyalkyl, polyethyleneoxy, aryl, aralkyl, heterocyclic, and wherein R.sub.5 and R.sub.6 taken together can form a ring which optionally contains at least one unsaturated bond; R.sub.7 and R.sub.8 are independently selected from the group consisting of hydrogen, alkyl, aralkyl, hydroxy, alkoxy, haloalkoxy, aryloxy, aralkoxy, hydroxyalkyl, acylamino, phenoxy, alkoxyalkoxy, sulphonylamino and halogen; wherein R.sub.2 and R.sub.3 are independently hydrogen, alkyl, alkoxy, hydroxyalkyl, aralkyl, aralkoxy and halogen; and R.sub.2 and R.sub.3 taken together can form a saturated or unsaturated carbocyclic ring; R.sub.4 is hydrogen, alkyl or substituted alkyl; and m is 1 or 2; i, j and k are independently 0 or 1; and A.sup.+ is an activity regulating group having the formula: ##STR71## where Z denotes the elements necessary to form a 5-membered heterocyclic ring, optionally having one or two double bonds: n is i or 2; and G.sup.- is a negatively charged ion. ### Claim 2 (depends on 1) The photographic material according to claim 1 wherein the activity regulating group A.sup.+ has the formula II: ##STR72## wherein Y and X denote the elements necessary to form a 5-membered heterocyclic ring having one or two double bonds; and Q is hydrogen or a ballasting group. ### Claim 3 (depends on 2) The photographic material according to claim 2 where B and C are the same and the compounds have the structure III: ##STR73## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as defined above, and Q is hydrogen or alkyl having from 1 to about 10 carbon atoms, a polyethyleneoxy group, an aryl group or a heterocyclic group, and G.sup.- is selected from the group consisting of Cl.sup.-, Br.sup.-, tosylate, and mesylate. ### Claim 4 (depends on 1) The photographic material according to claim 1 where the blocking group R.sub.1 has the formula VI ##STR74## wherein R.sub.8 is selected from the group consisting of hydrogen, halogen, alkoxy, alkyl, acylamino, and sulphonylamino. ### Claim 5 (depends on 1) The photographic material according to claim 1 wherein the blocking group R.sub.1 has the formula VII: ##STR75## wherein R.sub.5 and R.sub.6 each are independently selected from the group consisting of hydrogen, alkyl, aminoalkyl, alkylaminoalkyl, acylaminoalkyl, alkylsulphonylaminoalkyl, arylsulphonylaminoalkyl, trialkylammoniumalkyl, hydroxyalkyl, haloalkyl, cycloalkyl, alkoxyalkyl, polyethyleneoxy, aryl, aralkyl, and heterocyclic; wherein R.sub.5 and R.sub.6 taken together can form a substituted or unsubstituted heterocyclic ring; and n is 1 or 2. ### Claim 6 (depends on 2) The photographic material according to claim 2 wherein the activity regulating group A.sup.- is selected from the group consisting of: ##STR76## wherein R.sub.12 and R.sub.13 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, alkoxyalkoxy, aralkyl, aryl, aralkoxy, and halogen; R.sub.14 and R.sub.15 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, acylamino, aralkyl, aryl, aryloxy, and a heterocyclic group; and R.sub.16 and R.sub.17 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, alkoxylalkyl, aralkoxy, aryl, and halogen. ### Claim 7 (depends on 6) The photographic material according to claim 6 where the activity regulating group A.sup.+ has the formula: ##STR77## wherein R.sub.12 and R.sub.13 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, alkoxyalkoxy, aralkyl, aryl, aralkoxy, and halogen; and R.sub.14 is selected from the group consisting of hydrogen, alkyl, alkoxy, acylamino, aralkyl, aryl, aryloxy, and a heterocyclic group. ### Claim 8 (depends on 7) The photographic material according to claim 7, wherein R.sub.12 and R.sub.13 are independently selected from the group consisting of hydrogen, alkyl, and aryl; and R.sub.14 is selected from the group consisting of hydrogen, alkyl, aryl, aralkyl, and a heterocyclic group. ### Claim 9 (depends on 8) The photographic material according to claim 8 which has the formula X: ##STR78## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.12, R.sub.13, R.sub.14 and n are as defined above and G.sup.- is chloride or bromide. ### Claim 10 (depends on 3) The photographic material according to claim 3 where Q is hydrogen, an alkyl group having from 1 to 8 carbon atoms, an aryl group having from 6 to 8 carbon atoms, or a heterocyclic group having from 3 to 8 ring atoms. ### Claim 11 (depends on 10) The photographic material according to claim 10 where R.sub.4 is H or methyl. ### Claim 12 (depends on 3) The photographic material according to claim 3 wherein R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, methyl, ethyl, methoxy, ethoxy, hydroxyethyl, chloro and fluoro. ### Claim 13 (depends on 12) The photographic material according to claim 12 wherein R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, methyl, and methoxy. ### Claim 14 (depends on 1) The photographic material according claim 1 where the blocking group R.sub.1 has the formula V ##STR79## where in R.sub.7 is selected from the group consisting hydrogen, hydroxy, alkyl, alkoxy, phenoxy, halogen, hydroxyalkyl, alkoxyalkoxy, and hydroxyalkoxy; and m is 1 or 2. ### Claim 15 (depends on 14) The photographic material according to claim 14 wherein each R.sub.7 is independently selected from the group consisting of hydrogen, hydroxy, methyl, ethyl, methoxy, ethoxy, hydroxymethyl, hydroxyethyl, chloro, and fluoro; m is 1 and n is 2. ### Claim 16 (depends on 4) The photographic material according to claim 4 wherein R.sub.8 is selected from the group consisting of hydrogen, methoxy, ethoxy, halogen, alkyl having from 1 to about 10 carbon atoms, acylamino having from 1 to about 10 carbon atoms, and sulphonylamino having from 6 to 10 carbon atoms; k is 1 and n is 1. ### Claim 17 (depends on 5) The photographic material according to claim 5 wherein R.sub.5 and R.sub.6 are independently selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, haloalkyl, cycloalkyl, aralkyl and methoxyethyl; wherein each of the alkyl groups have from 1 to about 8 carbon atoms, each of the cycloalkyl groups have from 3 to about10 carbon atoms and the aryl groups have from 6 to about 8 carbon atoms, or R.sub.5 and R.sub.6 are taken together to form a heterocyclic ring having from 3 to 6 atoms and n is 2. ### Claim 18 (depends on 8) The photographic material according to claim 8 wherein R.sub.12 and R.sub.13 are independently selected from the group consisting of hydrogen, methyl, ethyl, methoxy, and ethoxy; and R.sub.14 is selected from the group consisting of hydrogen, alkyl having from 1 to about 8 carbon atoms, phenyl, tolyl, and benzyl, furyl and thienyl. ### Claim 19 (depends on 9) The photographic material according to claim 9 wherein R.sub.2, R.sub.3, R.sub.4, R.sub.12 and R.sub.13 are independently hydrogen or alkyl having from 1 to about 6 carbon atoms and R.sub.14 is alkyl having from 1 to about 8 carbon atoms. ### Claim 20 (depends on 19) The photographic material according to claim 19 wherein R.sub.1 is 2-hydroxymethylphenyl and R.sub.2, R.sub.3, R.sub.4, R.sub.12 and R.sub.13 are independently hydrogen or methyl. ### Claim 21 (depends on 20) The photographic material according to claim 20 wherein R.sub.2, R.sub.3, R.sub.4, R.sub.12 and R.sub.13 are hydrogen, R.sub.14 is ethyl and n is 1. ### Claim 22 (depends on 9) The photographic material according to claim 9 wherein the blocking group R.sub.1 is a 2-hydroxyanilyl group and n is 2. ### Claim 23 (depends on 22) The photographic material according to claim 22 wherein the blocking group R.sub.1 is 2-hydroxy-4-methylanilyl and R.sup.2, R.sup.3, R.sup.4, R.sup.12 and R.sup.13 are independently hydrogen or alkyl having from 1 to about 8 carbon atoms and n is 2. ### Claim 24 (depends on 23) The photographic material according to claim 23 wherein R.sub.2, R.sub.3, R.sub.4, R.sub.12 and R.sub.13 are hydrogen, R.sub.14 is ethyl. ### Claim 25 (depends on 9) The photographic material according to claim 9 wherein the blocking group R.sub.1 is a hydroxyalkylamino group and n is 2. ### Claim 26 (depends on 25) The photographic material according to claim 25 wherein the blocking group R.sub.1 is 2-hydroxyethyl amino and n is 2. ### Claim 27 (depends on 26) The photographic material according to claim 26 wherein R.sub.2, R.sub.3, R.sub.4, R.sub.12 and R.sub.13 are hydrogen, R.sub.14 is ethyl.