US3623873A - Development process in presence of a nitro-substituted benzothiadiazole or benzoselenadiazole - Google Patents
Development process in presence of a nitro-substituted benzothiadiazole or benzoselenadiazole Download PDFInfo
- Publication number
- US3623873A US3623873A US49902A US3623873DA US3623873A US 3623873 A US3623873 A US 3623873A US 49902 A US49902 A US 49902A US 3623873D A US3623873D A US 3623873DA US 3623873 A US3623873 A US 3623873A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- compound
- photographic
- formula
- nitro group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title abstract description 26
- -1 nitro-substituted benzothiadiazole Chemical class 0.000 title abstract description 22
- TVNJKAZMPQNGGE-UHFFFAOYSA-N 1,2,3-benzoselenadiazole Chemical compound C1=CC=C2[se]N=NC2=C1 TVNJKAZMPQNGGE-UHFFFAOYSA-N 0.000 title description 2
- 239000000463 material Substances 0.000 abstract description 22
- 150000001875 compounds Chemical class 0.000 abstract description 20
- 239000000839 emulsion Substances 0.000 abstract description 20
- 229910052709 silver Inorganic materials 0.000 abstract description 20
- 239000004332 silver Substances 0.000 abstract description 20
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 5
- 239000005864 Sulphur Substances 0.000 abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- 238000001879 gelation Methods 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 108010010803 Gelatin Proteins 0.000 description 7
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 229920000159 gelatin Polymers 0.000 description 7
- 239000008273 gelatin Substances 0.000 description 7
- 235000019322 gelatine Nutrition 0.000 description 7
- 235000011852 gelatine desserts Nutrition 0.000 description 7
- 229960000587 glutaral Drugs 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 229910052711 selenium Chemical group 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
- G03C1/346—Organic derivatives of bivalent sulfur, selenium or tellurium
Definitions
- R R N/ R4 where X represents a sulphur or selenium atom, at least one of R R R or R is a nitro group and the remainder are each selected from a hydrogen or a halogen atom, or
- This invention relates to the processing of silver halide photographic film material and in particular to the processing of photographic film material under conditions which tend to give rise to a high fog level in the processed material.
- antifoggant in silver halide photographic developing solutions because the actual development process tends to cause fog in the developed material.
- the usual antifoggant employed in developing solutions is a water-soluble bromide. However under certain conditions it is required to use a stronger antifoggant than bromide and for this purpose a number of organic antifoggants have been used.
- a process for the production of a photographic record which comprises developing photographic material having a gelatino silver halide emulsion and containing a developable silver image in a silver halide developing solution in the presence of a compound of the general formula:
- the rapid method comprises developing, washing and fixing the film material in solutions having an elevated temperature, usually 35 C. or above.
- the processing usually is carried out in a processing machine through which the photographic material is progressed by a roller system.
- a gelatin hardening agent such as glutaraldehyde
- the photographic material comprises a compound of the formula hereinbefore set forth the fog level in the developed material is reduced.
- a process for the production of a photographic record which comprises developing a photographic material having a gelatino silver halide emulsion and containing a developable silver salt image at a temperature above 30 C. in a developing solution containing a gelatin hardening agent, the said photographic material containing in at least one emulsion layer or in a layer adjacent thereto a compound of the general formula hereinbefore defined.
- the preferred gelatin hardening agent for use in this process is glutaric dialdehyde (glutaraldehyde) or a compound which comprises glutaric dialdehyde such as a bisulphi-te addition compound thereof.
- the preferred amount of a compound of the above formula to be' present in the emulsion of the photographic material for use in the process of the present invention is from 0.05 to 3.5 g. per gm. mole of silver halide present in the emulsion. It is preferred that a compound of the above formula is present in each emulsion layer of the photographic material. This is especially so in the case of X-ray film material wherein an emulsion layer is present on each side of the film support.
- the compounds of the above formula may however be present in a supercoat layer or in a sub-layer as long as this layer is adjacent to the emulsion layer.
- a sulphur and gold sensitized coarse-grained iodo bromide emulsion of the type suitable for X-ray photography with intensifying screens was divided into two parts. To the first portion was added the usual coating aids and hardening agents. The second portion was treated similarly but in addition there was added the quantity specified in Table II (which follows) the compound under test, dissolved in alcohol to form a 0.5% solution or dissolved in the requisite amount of dilute sodium hydroxide solution. Each emulsion was coated on a flexible support in the conventional manner.
- the samples were processed in a conventional machine designed to process radiographs in a dry-to-dry time of 90 seconds: the development phase of this process was 25 seconds at 40 C.
- the developing solution used was a l-phenyl 3 pyrazolidone/hydroquinone based developing solution which comprised 6 g./litre of glutaric dialdehyde.
- the Table II records the data of fog speed at a developed silver density of 1.0 and the average contrast over the density range of 0.2 to 2.0 for the control emulsion with no antifoggant and for the test emulsion containing the cited quantity of antifoggant per gm. mole of silver halide (the densities specified are measured from the fog density level and the speed figures are relative log speeds).
- R R R or R is a nitro group and the remainder are each selected from a hydrogen or a halogen atom, or an alkyl, aralkyl, alkoxy, monoor di-alkylamino, acylamino or a nitro group.
- a process for the production of a photographic record which comprises developing a photographic material having a gelatino silver halide emulsion and containing a developable silver salt image at a temperature above 30 C. in a developing solution containing a gelatin hardening agent, the process being characterised in that the said photographic material contains in at least one emulsion layer or in a layer adjacent thereto a compound of the formula:
- R R R or R is a nitro group and the remainder are each selected from a hydrogen or a halogen atom, or an alkyl, aralkyl, alkoxy, monoor di-alkylamino, acylamino or a nitro group.
- gelatin hardening agent is glutaraldehyde or a compound which comprises glutaraldehyde.
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Abstract
THIS APPLICATION DESCRIBES A PROCESS FOR THE PRODUCTION OF A PHOTOGRAPHIC RECORD WHICH COMPRISES DEVELOPING PHOTOGRAPHIC MATERIAL HAVING A GELATION SILVER HALIDE EMULSION CONTAINING A DEVELOPABLE SILVER IMAGE IN A SILVER HALIDE DEVELOPING SOLUTION THE PROCESS BEING CHARACTERISED IN THAT IT TAKES PLACE IN THE PRESENCE OF A COMPOUND OF THE FORMULA:
1,2-(=N-X-N=),3-R1,4-R2,5-R3,6-R4-BENZENE
WHERE X REPRESENTS A SULPHUR OR SELENIUM ATOMS, AT LEAST ONE OF R1, R2, R3 OR R4 IS A NITRO GROUP AND THE REMAINDER ARE EACH SELECTED FROM A HYDROGEN OR A HALOGEN ATOM, OR AN ALKYL, ARALKYL, ALKOXY, MONO- OR DI-ALKYLAMINO, ACYLAMINO OR A NITRO GROUP.
1,2-(=N-X-N=),3-R1,4-R2,5-R3,6-R4-BENZENE
WHERE X REPRESENTS A SULPHUR OR SELENIUM ATOMS, AT LEAST ONE OF R1, R2, R3 OR R4 IS A NITRO GROUP AND THE REMAINDER ARE EACH SELECTED FROM A HYDROGEN OR A HALOGEN ATOM, OR AN ALKYL, ARALKYL, ALKOXY, MONO- OR DI-ALKYLAMINO, ACYLAMINO OR A NITRO GROUP.
Description
United States Patent ()fice 3,623,873 Patented Nov. 30, 1971 3,623,873 DEVELOPMENT PROCESS IN PRESENCE OF A NITRO-SUBSTITUTED BENZOTHIADIAZOLE R BENZOSELENADIAZOLE John Colin Brown and Roy Anthony Cheer, llford, England, assignors to Ilford Limited, Ilford, Essex, England No Drawing. Filed June 25, 1970, Ser. No. 49,902 Claims priority, application Great Britain, June 26, 1969, 32,425/ 69 Int. Cl. G03c /30, 1/34 US. Cl. 96-665 5 Claims ABSTRACT OF THE DISCLOSURE This application describes a process for the production of a photographic record which comprises developing photographic material having a gelatino silver halide emulsion containing a developable silver image in a silver halide developing solution the process being characterised in that it takes place in the presence of a compound of the formula:
I N R N/ R4 where X represents a sulphur or selenium atom, at least one of R R R or R is a nitro group and the remainder are each selected from a hydrogen or a halogen atom, or
an alkyl, aralkyl, alkoxy, monoor di-alkylamino, acylamino or a nitro group.
This invention relates to the processing of silver halide photographic film material and in particular to the processing of photographic film material under conditions which tend to give rise to a high fog level in the processed material.
It is usual to include an antifoggant in silver halide photographic developing solutions because the actual development process tends to cause fog in the developed material. The usual antifoggant employed in developing solutions is a water-soluble bromide. However under certain conditions it is required to use a stronger antifoggant than bromide and for this purpose a number of organic antifoggants have been used.
It is the object of the present invention to provide a photographic development process wherein certain novel antifoggants are used.
According to the present invention therefore there is provided a process for the production of a photographic record which comprises developing photographic material having a gelatino silver halide emulsion and containing a developable silver image in a silver halide developing solution in the presence of a compound of the general formula:
be developed at an elevated temperature. An example of a photographic development process which employs an elevated temperature, i.e. a temperature above 30 C. is the so-called rapid" method of processing X-ray film.
The rapid method comprises developing, washing and fixing the film material in solutions having an elevated temperature, usually 35 C. or above. The processing usually is carried out in a processing machine through which the photographic material is progressed by a roller system. For this reason it is usual to include in the developing solution a gelatin hardening agent such as glutaraldehyde, in order to prevent the swollen gelatin from being badly marked by the rollers. It has been found that such a process wherein the developing solution is at an elevated temperature and comprises a gelatin hardening agent tends to cause excessively high fog levels in photographic material processed therein. However when the photographic material comprises a compound of the formula hereinbefore set forth the fog level in the developed material is reduced.
According to a particular embodiment of the present invention there is provided a process for the production of a photographic record which comprises developing a photographic material having a gelatino silver halide emulsion and containing a developable silver salt image at a temperature above 30 C. in a developing solution containing a gelatin hardening agent, the said photographic material containing in at least one emulsion layer or in a layer adjacent thereto a compound of the general formula hereinbefore defined.
The preferred gelatin hardening agent for use in this process is glutaric dialdehyde (glutaraldehyde) or a compound which comprises glutaric dialdehyde such as a bisulphi-te addition compound thereof.
The preferred amount of a compound of the above formula to be' present in the emulsion of the photographic material for use in the process of the present invention is from 0.05 to 3.5 g. per gm. mole of silver halide present in the emulsion. It is preferred that a compound of the above formula is present in each emulsion layer of the photographic material. This is especially so in the case of X-ray film material wherein an emulsion layer is present on each side of the film support. The compounds of the above formula may however be present in a supercoat layer or in a sub-layer as long as this layer is adjacent to the emulsion layer.
However the compounds of use in the process of the present invention may be present initially in the developing solution.
The following example will serve to illustrate the invention.
EXAMPLE In the example compounds which fall within the above defined formula as set forth in Table I which follows were used. In Table I the headings X, R R R and R refer to the symbols used in the formula as hereinbefore set forth.
A sulphur and gold sensitized coarse-grained iodo bromide emulsion of the type suitable for X-ray photography with intensifying screens was divided into two parts. To the first portion was added the usual coating aids and hardening agents. The second portion was treated similarly but in addition there was added the quantity specified in Table II (which follows) the compound under test, dissolved in alcohol to form a 0.5% solution or dissolved in the requisite amount of dilute sodium hydroxide solution. Each emulsion was coated on a flexible support in the conventional manner. After exposure through a wedge to a light source the spectral characteristics of which matched the emission from a calcium tungstate intensifying screen, the samples were processed in a conventional machine designed to process radiographs in a dry-to-dry time of 90 seconds: the development phase of this process was 25 seconds at 40 C. The developing solution used was a l-phenyl 3 pyrazolidone/hydroquinone based developing solution which comprised 6 g./litre of glutaric dialdehyde. The Table II records the data of fog speed at a developed silver density of 1.0 and the average contrast over the density range of 0.2 to 2.0 for the control emulsion with no antifoggant and for the test emulsion containing the cited quantity of antifoggant per gm. mole of silver halide (the densities specified are measured from the fog density level and the speed figures are relative log speeds).
TAB LE II Quantity Average Compound No. in mg. Fog Speed contrast It is observed from this table that the control emulsions showed a high fog level and low contrast whereas the test emulsions, each containing a compound of the formula as hereinbefore set forth, have a relatively low fog and a high contrast. These qualities are particularly desired in radiographs.
We claim as our invention:
1. A process for the production of a photographic record which comprises developing photographic material having a gelatino silver halide emulsion containing a developable silver image in a silver halide developing solution the process being characterised in that it takes place in the presence of a compound of the formula:
I N R;
j X B2 s I N Br where X represents a sulphur or selenium atom, at least one of R R R or R is a nitro group and the remainder are each selected from a hydrogen or a halogen atom, or an alkyl, aralkyl, alkoxy, monoor di-alkylamino, acylamino or a nitro group.
2. A process according to claim 1 wherein the compound of the formula defined therein is present initially in the photographic material.
3. A process according to claim 2 wherein the compound of the formula defined in claim 1 is present in each silver halide emulsion layer of the photographic material.
4. A process for the production of a photographic record which comprises developing a photographic material having a gelatino silver halide emulsion and containing a developable silver salt image at a temperature above 30 C. in a developing solution containing a gelatin hardening agent, the process being characterised in that the said photographic material contains in at least one emulsion layer or in a layer adjacent thereto a compound of the formula:
where X represents a sulphur or selenium atom, at least one of R R R or R is a nitro group and the remainder are each selected from a hydrogen or a halogen atom, or an alkyl, aralkyl, alkoxy, monoor di-alkylamino, acylamino or a nitro group.
5. A process according to claim 4 wherein the gelatin hardening agent is glutaraldehyde or a compound which comprises glutaraldehyde.
References Cited UNITED STATES PATENTS 2,131,038 9/1938 Brooker et al. 96109 2,271,229 1/ 1942 Peterson et al. 96-66.5 3,326,681 6/1967 Walworth 96---1O9 3,545,971 12/1970 Barnes et al. 9663 FOREIGN PATENTS 960,675 6/ 1964 Great Britain 96-109 NORMAN G. TORCHIN, Primary Examiner M. F. KELLEY, Assistant Examiner US. Cl. X.R. 9695, 109
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB32425/69A GB1244426A (en) | 1969-06-26 | 1969-06-26 | Photographic development process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3623873A true US3623873A (en) | 1971-11-30 |
Family
ID=10338408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US49902A Expired - Lifetime US3623873A (en) | 1969-06-26 | 1970-06-25 | Development process in presence of a nitro-substituted benzothiadiazole or benzoselenadiazole |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3623873A (en) |
| JP (1) | JPS4927698B1 (en) |
| BE (1) | BE752612A (en) |
| DE (1) | DE2031314A1 (en) |
| GB (1) | GB1244426A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0694808A1 (en) * | 1994-07-29 | 1996-01-31 | Dainippon Ink And Chemicals, Inc. | Process of forming super high-contrast negative images and silver halide photographic material and developer being used therefor |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5066572A (en) * | 1990-03-22 | 1991-11-19 | Eastman Kodak Company | Control of pressure-fog with gelatin-grafted and case-hardened gelatin-grafted soft polymer latex particles |
-
1969
- 1969-06-26 GB GB32425/69A patent/GB1244426A/en not_active Expired
-
1970
- 1970-06-24 DE DE19702031314 patent/DE2031314A1/en active Pending
- 1970-06-25 US US49902A patent/US3623873A/en not_active Expired - Lifetime
- 1970-06-26 BE BE752612D patent/BE752612A/en unknown
- 1970-06-26 JP JP45055328A patent/JPS4927698B1/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0694808A1 (en) * | 1994-07-29 | 1996-01-31 | Dainippon Ink And Chemicals, Inc. | Process of forming super high-contrast negative images and silver halide photographic material and developer being used therefor |
| US5683854A (en) * | 1994-07-29 | 1997-11-04 | Dainippon Ink And Chemicals Inc. | Process of forming super high-contrast negative images and silver halide photographic material and developer being used therefor |
| US5766833A (en) * | 1994-07-29 | 1998-06-16 | Dainippon Ink And Chemicals Inc. | Process of forming super high-contrast negative images and silver halide photographic material and developer being used therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4927698B1 (en) | 1974-07-19 |
| BE752612A (en) | 1970-12-01 |
| DE2031314A1 (en) | 1971-01-07 |
| GB1244426A (en) | 1971-09-02 |
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