US4686167A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Compositions comprising ethane dioic acid hydrazide compounds and derivatives useful as dot-promoting agents
Assignee: ANITEC IMAGE Corp A CORP OF
•
Filing: 1985-09-26
•
Granted: 1987-08-11
•
Expires: 2005-09-26
Abstract
Abstract Disclosed are novel compounds of the formula: ##STR1## wherein: X=--NR 5 R 6 , or --OR 7 ; R 1 and R 2 are independently hydrogen, substituted or unsubstituted alkyl, haloalkyl, hydroxyalkyl alkoxyalkyl, alkylaminoalkyl or arylalkyl having up to 18 carbons; cycloalkyl; phenyl or naphthyl; alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituents. R 3 is hydrogen, benzyl, alkoxybenzyl, halobenzyl or alkylbenzyl, provided that if neither R 1 nor R 2 is hydrogen, then R 3 is hydrogen. R 4 is a divalent aromatic group which is substituted or unsubstituted. R 5 , R 6 , and R 7 are independently hydrogen, alkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl, acylaminoalkyl, aminoalkyl or phenylalkyl having up to 12 carbons; a cycloalkyl substituent; phenyl or naphthyl; an alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituent. Furthermore, either R 1 and R 3 or R 1 and R 2 can be linked to form a heterocyclic ring system containing 3-10 atoms. Additionally, R 5 and R 6 can be linked to form a heterocyclic ring system containing 3-10 atoms. Y is an oxygen or sulfur atom. If Y is sulfur then n-1, if Y is oxygen then n=0 or 1. These compounds are useful as high-quality dot promoting agents in negative-working photographic systems. Disclosed as well are radiation-sensitive compositions and elements containing such dot promoting agents in combination with silver halide grains. These exposed compositions and elements when processed in a developer containing a dihydroxybenzene developing agent, a substituted benzotriazole, a sulfite preservative and an amine compound provide a method for the production of halftone dots possessing high image quality.
Inventors
- 👤 Bruce M. Resnick
- 👤 Allan J. Wexler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 15:56
CPC Classifications
C; C07; C07C; C07C243/00; G; G03; G03C; G03C1/00; G03C1/005; G03C1/06; G03C1/061; Y; Y10; Y10S; Y10S430/00; Y10S430/15
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
243 words
A silver halide photographic emulsion comprising radiation-sensitive silver halide grains capable of forming a surface-latent image, a binder and a dot quality-promoting amount of a compound of the formula: ##STR39## wherein: X=NR 5 R 6 , or --OR 7 ; R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, alkylaminoalkyl and arylalkyl substituents having up to 18 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl, and alkoxyphenyl substituents; R 3 is selected from the group consisting of hydrogen, benzyl, alkoxybenzyl, halobenzyl and alkylbenzyl substituents provided that R 3 is hydrogen when neither R 1 nor R 2 are hydrogen; wherein R 1 and R 2 or R 1 and R 3 can be linked together to form a heterocyclic ring system having 3-10 carbon atoms; R 4 is a divalent aromatic group with the two valences being ortho- or para- to each other said group being substituted or unsubstituted; R 5 , R 6 and R 7 are independently selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl, acylaminoalkyl, aminoalkyl and phenylalkyl substituents having up to 12 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl and alkoxyphenyl substituents; and wherein R 5 and R 6 can be linked to form a heterocyclic ring system containing 3-10 atoms; Y is selected from the group consisting of sulfur and oxygen atoms; n is zero or one; provided that n=1 when Y is sulfur.
Claim 2
Dependent Claim
243 words
A silver halide photographic emulsion comprising radiation-sensitive silver halide grains capable of forming a surface-latent image, a binder and a dot quality-promoting amount of a compound of the formula: ##STR39## wherein: X=NR 5 R 6 , or --OR 7 ; R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, alkylaminoalkyl and arylalkyl substituents having up to 18 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl, and alkoxyphenyl substituents; R 3 is selected from the group consisting of hydrogen, benzyl, alkoxybenzyl, halobenzyl and alkylbenzyl substituents provided that R 3 is hydrogen when neither R 1 nor R 2 are hydrogen; wherein R 1 and R 2 or R 1 and R 3 can be linked together to form a heterocyclic ring system having 3-10 carbon atoms; R 4 is a divalent aromatic group with the two valences being ortho- or para- to each other said group being substituted or unsubstituted; R 5 , R 6 and R 7 are independently selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl, acylaminoalkyl, aminoalkyl and phenylalkyl substituents having up to 12 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl and alkoxyphenyl substituents; and wherein R 5 and R 6 can be linked to form a heterocyclic ring system containing 3-10 atoms; Y is selected from the group consisting of sulfur and oxygen atoms; n is zero or one; provided that n=1 when Y is sulfur.
Claim 3
Dependent Claim
41 words
An emulsion accoring to claim 1 wherein: R 4 is selected from the group consisting of phenylene and alkyl-, halo- and alkoxy-substituted phenylene with the thioamido or amido moiety of said compound being ortho- or para- relative to the hydrazino moiety.
Claim 4
Dependent Claim
8 words
An emulsion according to claim 1, wherein: Y=S.
Claim 5
Dependent Claim
12 words
An emulsion according to claim 1, wherein: X=NR 5 R 6 .
Claim 6
Dependent Claim
10 words
An emulsion according to claim 1, wherein: X=OR 7 .
Claim 7
Dependent Claim
104 words
A silver halide photographic emulsion comprising radiation-sensitive silver halide grains capable of forming a surface-latent image, a binder and a dot quality-promoting amount of a compound of the formula: ##STR40## wherein Y=O or S; Z=O or NH; R 8 is selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl and arylalkyl substituents having up to 18 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl, and alkoxyphenyl substituents; and R 9 is selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl, acylaminoalkyl, aminoalkyl and phenylalkyl substituents having up to 12 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl and alkoxyphenyl substituents.
Claim 8
Dependent Claim
104 words
A silver halide photographic emulsion comprising radiation-sensitive silver halide grains capable of forming a surface-latent image, a binder and a dot quality-promoting amount of a compound of the formula: ##STR40## wherein Y=O or S; Z=O or NH; R 8 is selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl and arylalkyl substituents having up to 18 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl, and alkoxyphenyl substituents; and R 9 is selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl, acylaminoalkyl, aminoalkyl and phenylalkyl substituents having up to 12 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl and alkoxyphenyl substituents.
Claim 9
Dependent Claim
241 words
A radiation-sensitive photographic element comprising: (a) a support; (b) a photographic emulsion comprising: (i) a binder; and (ii) radiation-sensitive silver halide grains capable of forming a surface-latent image; and (c) incorporated in said emulsion or in another protective hydrophilic colloid layer, a dot-quality promoting amount of a compound of the formula: ##STR41## wherein: X=NR 5 R 6 , or --OR 7 ; R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, alkylaminoalkyl and arylalkyl substituents having up to 18 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl, and alkoxyphenyl substituents; R 3 is selected from the group consisting of hydrogen, benzyl, alkoxybenzyl, halobenzyl and alkylbenzyl substituents provided that R 3 is hydrogen when neither R 1 nor R 2 are hydrogen; R 4 is a divalent aromatic group which is substituted or unsubstituted, said two valences of said aromatic group being ortho- or para- to each other; R 5 , R 6 and R 7 are independently selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl, acylaminoalkyl, aminoalkyl and phenylalkyl substituents having up to 12 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl and alkoxyphenyl substituents; and wherein R 5 and R 6 can be linked to form a heterocyclic ring system containing 3-10 atoms; Y is selected from the group consisting of sulfur and oxygen atoms; n is zero or one; provided that n=1 when Y is sulfur.
Claim 10
Dependent Claim
241 words
A radiation-sensitive photographic element comprising: (a) a support; (b) a photographic emulsion comprising: (i) a binder; and (ii) radiation-sensitive silver halide grains capable of forming a surface-latent image; and (c) incorporated in said emulsion or in another protective hydrophilic colloid layer, a dot-quality promoting amount of a compound of the formula: ##STR41## wherein: X=NR 5 R 6 , or --OR 7 ; R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, alkylaminoalkyl and arylalkyl substituents having up to 18 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl, and alkoxyphenyl substituents; R 3 is selected from the group consisting of hydrogen, benzyl, alkoxybenzyl, halobenzyl and alkylbenzyl substituents provided that R 3 is hydrogen when neither R 1 nor R 2 are hydrogen; R 4 is a divalent aromatic group which is substituted or unsubstituted, said two valences of said aromatic group being ortho- or para- to each other; R 5 , R 6 and R 7 are independently selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl, acylaminoalkyl, aminoalkyl and phenylalkyl substituents having up to 12 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl and alkoxyphenyl substituents; and wherein R 5 and R 6 can be linked to form a heterocyclic ring system containing 3-10 atoms; Y is selected from the group consisting of sulfur and oxygen atoms; n is zero or one; provided that n=1 when Y is sulfur.
Claim 11
Dependent Claim
41 words
A photographic element according to claim 7, wherein: R 4 is selected from the group consisting of phenylene and alkyl-, halo- and alkoxy-substituted phenylene with the thioamido or amido moiety of said compound being ortho- or para-relative to the hydrazino moiety.
Claim 12
Dependent Claim
9 words
A photographic element according to claim 7, wherein: Y=S.
Claim 13
Dependent Claim
13 words
A photographic element according to claim 7, wherein: X=NR 5 R 6 .
Claim 14
Dependent Claim
11 words
A photographic element according to claim 7, wherein: X=OR 7 .
Claim 15
Dependent Claim
126 words
A radiation-sensitive photographic element comprising: (a) a support; (b) a photographic emulsion comprising: (i) a binder; and (ii) radiation-sensitive silver halide grains capable of forming a surface-latent image; and (c) incorporated in said emulsion or in another protective hydrophilic colloid layer, a dot-quality promoting amount of a compound of the formula: ##STR42## wherein Y=O or S; Z=O or NH; R 8 is selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl and arylalkyl substituents having up to 18 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl, and alkoxyphenyl substituents; and R 9 is selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl, acylaminoalkyl, aminoalkyl and phenylalkyl substituents having up to 12 carbon atoms, cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl and alkoxyphenyl substituents.
Claim 16
Dependent Claim
126 words
A radiation-sensitive photographic element comprising: (a) a support; (b) a photographic emulsion comprising: (i) a binder; and (ii) radiation-sensitive silver halide grains capable of forming a surface-latent image; and (c) incorporated in said emulsion or in another protective hydrophilic colloid layer, a dot-quality promoting amount of a compound of the formula: ##STR42## wherein Y=O or S; Z=O or NH; R 8 is selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl and arylalkyl substituents having up to 18 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl, and alkoxyphenyl substituents; and R 9 is selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl, acylaminoalkyl, aminoalkyl and phenylalkyl substituents having up to 12 carbon atoms, cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl and alkoxyphenyl substituents.
Claim 17
Dependent Claim
17 words
A photographic element according to claim 12, said element further comprising an antifoggant and a sensitizing agent.
Claim 18
Independent Claim
275 words
A method for producing high dot-quality images comprising imagewise exposing a radiation-sensitive photographic element comprising: (a) a support; (b) a photographic emulsion comprising: (i) a binder; and (ii) radiation-sensitive silver halide grains capable of forming a surface-latent image; and (c) incorporated in said emulsion or in another protective hydrophilic colloid layer, a dot-quality promoting amount of a compound of the formula: ##STR43## wherein: X=NR 5 R 6 , or --OR 7 ; R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, alkylaminoalkyl and arylalkyl substituents having up to 18 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl, and alkoxyphenyl substituents; R 3 is selected from the group consisting of hydrogen, benzyl, alkoxybenzyl, halobenzyl and alkylbenzyl substituents provided that R 3 is hydrogen when neither R 1 nor R 2 are hydrogen; wherein R 1 and R 2 or R 1 and R 3 can be linked together to form a heterocyclic ring system having 3-10 carbon atoms; R 4 is a divalent aromatic group with the two valences being ortho- or para- to each other said group being substituted or unsubstituted; R 5 , R 6 and R 7 are independently selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl, acylaminoalkyl, aminoalkyl and phenylalkyl substituents having up to 12 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl and alkoxyphenyl substituents; and wherein R 5 and R 6 can be linked to form a heterocyclic ring system containing 3-10 atoms; Y is selected from the group consisting of sulfur and oxygen atoms; n is zero or one; provided that n=1 when Y is sulfur.
Claim 19
Independent Claim
275 words
A method for producing high dot-quality images comprising imagewise exposing a radiation-sensitive photographic element comprising: (a) a support; (b) a photographic emulsion comprising: (i) a binder; and (ii) radiation-sensitive silver halide grains capable of forming a surface-latent image; and (c) incorporated in said emulsion or in another protective hydrophilic colloid layer, a dot-quality promoting amount of a compound of the formula: ##STR43## wherein: X=NR 5 R 6 , or --OR 7 ; R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, alkylaminoalkyl and arylalkyl substituents having up to 18 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl, and alkoxyphenyl substituents; R 3 is selected from the group consisting of hydrogen, benzyl, alkoxybenzyl, halobenzyl and alkylbenzyl substituents provided that R 3 is hydrogen when neither R 1 nor R 2 are hydrogen; wherein R 1 and R 2 or R 1 and R 3 can be linked together to form a heterocyclic ring system having 3-10 carbon atoms; R 4 is a divalent aromatic group with the two valences being ortho- or para- to each other said group being substituted or unsubstituted; R 5 , R 6 and R 7 are independently selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl, acylaminoalkyl, aminoalkyl and phenylalkyl substituents having up to 12 carbon atoms; cycloalkyl, phenyl, naphthyl, alkylphenyl, cyanophenyl, halophenyl and alkoxyphenyl substituents; and wherein R 5 and R 6 can be linked to form a heterocyclic ring system containing 3-10 atoms; Y is selected from the group consisting of sulfur and oxygen atoms; n is zero or one; provided that n=1 when Y is sulfur.
Claim 20
Dependent Claim
62 words
A method for producing high dot-quality images comprising imagewise exposing a radiation-sensitive photographic element comprising: (a) a support; (b) a photographic emulsion comprising: (i) a binder; and (ii) radiation-sensitive silver halide grains capable of forming a surface-latent image; and (c) incorporated in said emulsion or in another protective hydrophilic colloid layer, a dot-quality promoting amount of a compound according to claim 2.
Claim 21
Dependent Claim
62 words
A method for producing high dot-quality images comprising imagewise exposing a radiation-sensitive photographic element comprising: (a) a support; (b) a photographic emulsion comprising: (i) a binder; and (ii) radiation-sensitive silver halide grains capable of forming a surface-latent image; and (c) incorporated in said emulsion or in another protective hydrophilic colloid layer, a dot-quality promoting amount of a compound according to claim 3.
Claim 22
Dependent Claim
62 words
A method for producing high dot-quality images comprising imagewise exposing a radiation-sensitive photographic element comprising: (a) a support; (b) a photographic emulsion comprising: (i) a binder; and (ii) radiation-sensitive silver halide grains capable of forming a surface-latent image; and (c) incorporated in said emulsion or in another protective hydrophilic colloid layer, a dot-quality promoting amount of a compound according to claim 5.
Claim 23
Dependent Claim
7 words
A photographic element according to claim 6.
Claim 24
Dependent Claim
62 words
A method for producing high dot-quality images comprising imagewise exposing a radiation-sensitive photographic element comprising: (a) a support; (b) a photographic emulsion comprising: (i) a binder; and (ii) radiation-sensitive silver halide grains capable of forming a surface-latent image; and (c) incorporated in said emulsion or in another protective hydrophilic colloid layer, a dot-quality promoting amount of a compound according to claim 7.
Claim 25
Dependent Claim
62 words
A method for producing high dot-quality images comprising imagewise exposing a radiation-sensitive photographic element comprising: (a) a support; (b) a photographic emulsion comprising: (i) a binder; and (ii) radiation-sensitive silver halide grains capable of forming a surfact-latent image; and (c) incorporated in said emulsion or in another protective hydrophilic colloid layer, a dot-quality promoting amount of a compound according to claim 11.
Claim 26
Dependent Claim
43 words
A method according to claim 20 further comprising developing said exposed element in a developing solution having a pH not higher than 12.3 and comprising a dihydroxybenzene developing agent, a benzotriazole antifoggant, an amine, and more than 0.15 mole of a sulfite ion.
Claim 27
Dependent Claim
28 words
A silver halide emulsion according to claim 6 further comprising a sensitizing agent, an antifoggant, a surfactant coating aid and a pepper-grain reducing amount of a bisulfite compound.
Claim 28
Dependent Claim
16 words
A method according to claim 21, wherein said solution comprises hydroquinone, 5-methylbenzotriazole, diethylaminopropanediol, and sodium sulfite.
References Cited (Backward Citations)
US3227552A
Cited
US4221857A
Cited
US4272606A
Cited
CA1146001A
Cited
US4243739A
Cited
US4272614A
Cited
US4385108A
Cited
US4323643A
Cited
US4269929A
Cited
US4429036A
Cited
US4447522A
Cited
US4459347A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-08-10 | 1991-02-09 | 1991-08-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-08-10 | 1995-02-09 | 1995-08-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-08-10 | 1999-02-09 | 1999-08-11 | $7700.00 | Window Closed / Lapsed |