US2657136A - Photographic antiplumming agents and compositions containing them - Google Patents
Photographic antiplumming agents and compositions containing them Download PDFInfo
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- US2657136A US2657136A US253206A US25320651A US2657136A US 2657136 A US2657136 A US 2657136A US 253206 A US253206 A US 253206A US 25320651 A US25320651 A US 25320651A US 2657136 A US2657136 A US 2657136A
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- United States
- Prior art keywords
- silver halide
- photographic
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- grams
- emulsion
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- 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
- G03C1/35—Antiplumming agents, i.e. antibronzing agents; Toners
- G03C1/355—Organic derivatives of bivalent sulfur, selenium or tellurium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/13—Antibronze agent or process
Definitions
- This invention relates to improvements in the production of photographic images, especially images on paper supports prepared from silver halide emulsions.
- Silver halide emulsions are frequently subject to image degradation during processing, that is, during development, fixing, washing, toning, or other treatment and during the moist heat to which they are subjected on drying, as when prints are subjected to ferrotyping or hot-type glazing. This degradation of the image frequently manifests itself as plumming or bronzing of the image.
- o-phenylene, o-naphthylene, etc. which may be which can be represented by the following general formula:
- D represents an arylene group, e. g. o-phenylene, o-naphthylene, etc., which may be unsubstituted or substituted, for example, with an alkyl (e. g. methyl, ethyl, etc.) and/or alkoxyl (e. g. methoxy, ethoxy, etc.) group
- R represents an alkyl group, e. g. methyl, ethyl, etc.
- R1 represents an acyl group, e. g. acetyl, propionyl, etc. can be hydrolyzed in alkaline media to give hydrolysates which not only are effective antiplumming agents, but which, upon prolonged standing, develop only a faint yellow colour and show no increase in desensitizing properties.
- an object of our invention to provide a means for preventing image degradation in an exposed silver halide emulsion. Still another object is to provide new chemical compounds. Another object is to provide a method for making these new compounds. Another object is to provide photographic silver halide emulsions containing these new compounds. Other objects will become apparent from a consideration of the following examples and description.
- the present invention provides a method of preventing image degradation of an exposed silver halide emulsion during processing which comprises performing one or more of the steps of developing, fixing, washing and drying an exposed silver halide emulsion in the presence of one or more compounds represented by the following general formula:
- D represents an arylene group, e. g.
- alkyl e. g. methyl, ethyl, etc.
- alkoxyl e. g. methoxy, ethoxy, etc.
- R represents an alkyl group, e. g. methyl, ethyl, etc.
- R2 represents a hydrogen atom or a metallic atom, such as a sodium atom, potassium atom orother alkali metal atom.
- Example 8 2-a-mercaptobutyramidobenzthiazOZe Z-aminobenzthiazole (7.5 g.) was dissolved in dioxane (50 cc.) by warming, quinoline (6.5 g.) was added, and stirring rapidly, aacetylthio butyryl chloride (9.0 g.) dripped in over 10 minutes at 25 C. Quinoline hydrochloride separated rapidly. After completed addition the mixture was stirred for 2 hours and poured into water (250 00.). A thick yellow oil was precipitated. It was taken up in chloroform and the solvent distilled oil.
- the residual oil was dissolved in ethanol (50 cc.) and a solution of sodium hydroxide (6.0 g.) in water (250 cc.) added at 25 C. After 2 minutes water (250 cc.) was added, the liquor clarified by ether extraction and the required thiol precipitated as a semisolid with dilute hydrochloric acid. This was washed by decantation, redissolved in 0.5N-sodium hydroxide, clarified by ether extraction and precipitated as a hard solid by acidification. It was collected, washed with water and air dried. From benzene it formed cream needles, M. P. 142-146 C.
- Example 8 The a-acetylthiobutyryl chloride used in Example 8 was prepared as shown in the following example:
- Example 9.a-Acetylbutyrylchloride a-Acetylthiobutyric acid (73 g.) was treated at 2025 C. with thionyl chloride (67.4 g.), stood overnight, excess thionyl chloride distilled off at 6065 C. under reduced pressure (20 mm.) and the oil distilled from the steam bath at '70- 72 C./9 mm.
- Example 9 The a-acetylthiobutyric acid used in Example 9 was prepared as shown in the following example:
- Example 10 -a-Acetylthiobutyric acid a-Mercaptobutyric acid (52 g.) was placed in a 250 cc. B-necked flask fitted with stirrer and dropping funnel and acetic anhydride (75 cc.) run in over 10 minutes at room temperature. It was stirred for minutes, then the solvent removed under reduced pressure on the steam bath. The oil was then fractionated, collected at 100 150 C./8 mm. then redistilled and collected (37 g.) at 143-149" C./8 mm.
- the method of preventing image degradation of an exposed silver halide emulsion during processing which comprises performing at least one of the steps of developing, fixing, washing and drying said emulsion in the presence in said emulsion of from 2.5 grams to 25 grams per unit of silver halide formed from 1000 grams of silver nitrate, of a compound selected from those represented by the following general formula:
- R represents an alkyl group
- R2 represents a member selected from the group consistingof a hydrogen atom and an alkali metal atom
- D represents an arylene group
- the method of preventing image degradation of an exposed silver halide emulsion during processing which comprises performing at least one of the steps of developing, fixing, washing and drying said emulsion in the presence in said emulsion of from 2.5 grams to 25 grams per unit of silver halide formed from 1000 grams of silver nitrate, of a compound selected from those represented by the following general formula;
- R represents an alkyl group containing from 1 to 2 carbon atoms
- R2 represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom
- D represents a phenylene group
- R represents an alkyl group containing from 1 to 2 carbon atoms
- R2 represents a member selected from the group consisting of a hydragon atom and'an alkalirmetal-atom
- D represents a-phenylene group
- R represents an alkyl group
- R2 represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom
- D represents anary-lene group.
- R. represents an alkyl group containing from '1' to 2 carbon atoms
- R2 represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom
- D repre'sents'a phenylene group
- R2 represents a member selected from the group consisting of a hydrogen atom and D represents an arylene group.
- R2 represents a member selected from the group consisting of a hydrogen atom and Drepresents an arylene group.
- a photographic silver halide emulsion containingjrom 2.5 grams per unit to 25 grams per unit of silver halide formed from 1000 grams of silvernitrate of acompound selected from the group consisting of 2-a-mercaptopropionamidobenzthiazole, '2-'o.-mercaptopropionamido-6- ethoxybenzthiazole, 2-a-mercaptopropionamido- 6-methoxybenzthiazo1e, 6 Ch 1QI0-2-a-II1BICaptO propionamidobenzthiazole, "zfa mercaptobutyramidob'enz'thiazole, and alkali metal salts of said compounds.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
Patented Oct. 27, 1953 PHOTOGRAPHIC ANTIPLUMMING AGENTS AND COMPOSITIONS CONTAINING THEM Edward B. Knott and Philip K. Brooks, Harrow,
England, assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application October 25, 1951, Serial No. 253,206. In Great Britain March 30, 1951 9 Claims.
This invention relates to improvements in the production of photographic images, especially images on paper supports prepared from silver halide emulsions.
Silver halide emulsions are frequently subject to image degradation during processing, that is, during development, fixing, washing, toning, or other treatment and during the moist heat to which they are subjected on drying, as when prints are subjected to ferrotyping or hot-type glazing. This degradation of the image frequently manifests itself as plumming or bronzing of the image.
It is known that Z-acetylthioglycolamidobenzthiazole having the following formula:
can be employed as an anti-plumming agent for photographic silver halide emulsions. Moreover, the alkaline hydrolysis product of the above compound:
II. S
is an efficient anti-plumming agent. Attempts to isolate the free thiol:
III. S
o-phenylene, o-naphthylene, etc., which may be which can be represented by the following general formula:
IV. s
/ R D ONHC O-llH-SR;
wherein D represents an arylene group, e. g. o-phenylene, o-naphthylene, etc., which may be unsubstituted or substituted, for example, with an alkyl (e. g. methyl, ethyl, etc.) and/or alkoxyl (e. g. methoxy, ethoxy, etc.) group, R represents an alkyl group, e. g. methyl, ethyl, etc. and R1 represents an acyl group, e. g. acetyl, propionyl, etc. can be hydrolyzed in alkaline media to give hydrolysates which not only are effective antiplumming agents, but which, upon prolonged standing, develop only a faint yellow colour and show no increase in desensitizing properties.
It is, therefore, an object of our invention to provide a means for preventing image degradation in an exposed silver halide emulsion. Still another object is to provide new chemical compounds. Another object is to provide a method for making these new compounds. Another object is to provide photographic silver halide emulsions containing these new compounds. Other objects will become apparent from a consideration of the following examples and description.
Accordingly, the present invention provides a method of preventing image degradation of an exposed silver halide emulsion during processing which comprises performing one or more of the steps of developing, fixing, washing and drying an exposed silver halide emulsion in the presence of one or more compounds represented by the following general formula:
wherein D represents an arylene group, e. g.
unsubstituted or substituted, for example, with, alkyl (e. g. methyl, ethyl, etc.) and/or alkoxyl (e. g. methoxy, ethoxy, etc.) groups, R represents an alkyl group, e. g. methyl, ethyl, etc., and R2 represents a hydrogen atom or a metallic atom, such as a sodium atom, potassium atom orother alkali metal atom.
When any of the above compounds represented by Formula V are incorporated in silver halide .5 Example 6.--2-a-mercaptopropionamido-fimethoxybenzthiaeole Example 7.-6-chloro-2-a-mercaptopropionamidobenzthiazole To Z-amino-d-chlorobenzthiazole (6.7 g.) in dioxane (30 cc.) was added quinoline (4.7 g.), then a-acetylthiopropionyl chloride (6.0 g.). After 2 hours standing water (150 cc.) was added to give an oil. This was hydrolysed in ethanol (25 cc.) by adding a solution of sodium hydroxide (3.5 g.) in water (125 00.). The solid obtained on acidification formed a cream microcrystalline powder, M. P. 183-186" C. from benzene.
Example 8. 2-a-mercaptobutyramidobenzthiazOZe Z-aminobenzthiazole (7.5 g.) was dissolved in dioxane (50 cc.) by warming, quinoline (6.5 g.) was added, and stirring rapidly, aacetylthio butyryl chloride (9.0 g.) dripped in over 10 minutes at 25 C. Quinoline hydrochloride separated rapidly. After completed addition the mixture was stirred for 2 hours and poured into water (250 00.). A thick yellow oil was precipitated. It was taken up in chloroform and the solvent distilled oil. The residual oil was dissolved in ethanol (50 cc.) and a solution of sodium hydroxide (6.0 g.) in water (250 cc.) added at 25 C. After 2 minutes water (250 cc.) was added, the liquor clarified by ether extraction and the required thiol precipitated as a semisolid with dilute hydrochloric acid. This was washed by decantation, redissolved in 0.5N-sodium hydroxide, clarified by ether extraction and precipitated as a hard solid by acidification. It was collected, washed with water and air dried. From benzene it formed cream needles, M. P. 142-146 C.
The a-acetylthiobutyryl chloride used in Example 8 was prepared as shown in the following example:
Example 9.a-Acetylbutyrylchloride a-Acetylthiobutyric acid (73 g.) was treated at 2025 C. with thionyl chloride (67.4 g.), stood overnight, excess thionyl chloride distilled off at 6065 C. under reduced pressure (20 mm.) and the oil distilled from the steam bath at '70- 72 C./9 mm.
The a-acetylthiobutyric acid used in Example 9 was prepared as shown in the following example:
Example 10.-a-Acetylthiobutyric acid a-Mercaptobutyric acid (52 g.) was placed in a 250 cc. B-necked flask fitted with stirrer and dropping funnel and acetic anhydride (75 cc.) run in over 10 minutes at room temperature. It was stirred for minutes, then the solvent removed under reduced pressure on the steam bath. The oil was then fractionated, collected at 100 150 C./8 mm. then redistilled and collected (37 g.) at 143-149" C./8 mm.
Other compounds represented by Formula V above can also be used effectively according to our invention.
What {we claim as our invention and desire secured by Letters Patent of the United States is:
1. The method of preventing image degradation of an exposed silver halide emulsion during processing, which comprises performing at least one of the steps of developing, fixing, washing and drying said emulsion in the presence in said emulsion of from 2.5 grams to 25 grams per unit of silver halide formed from 1000 grams of silver nitrate, of a compound selected from those represented by the following general formula:
D c-NH-o o- H-SR,
\N/ wherein R represents an alkyl group, R2 represents a member selected from the group consistingof a hydrogen atom and an alkali metal atom, and D represents an arylene group.
2. The method of preventing image degradation of an exposed silver halide emulsion during processing, which comprises performing at least one of the steps of developing, fixing, washing and drying said emulsion in the presence in said emulsion of from 2.5 grams to 25 grams per unit of silver halide formed from 1000 grams of silver nitrate, of a compound selected from those represented by the following general formula;
wherein R represents an alkyl group containing from 1 to 2 carbon atoms, R2 represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom, and D represents a phenylene group.
3. The method of preventing image degradation of an exposed silver halide emulsion during processing, which comprises incorporating in at least one of the developing, fixing and washing baths used to process said emulsion, an appreciable amount but not more than 5%, of a compound selected from those represented by the following general formula:
wherein R represents an alkyl group containing from 1 to 2 carbon atoms, R2 represents a member selected from the group consisting of a hydragon atom and'an alkalirmetal-atom, and D represents a-phenylene group, and processing said exposed emulsioninsaid-bath.
5. A photographic silver halide emulsion containing from 2.5 to 25 rams penu i Of Silver halide formed from 1000,grarns;of; silver nitrate, of ahompound selected from those represented by the following general formula:
wherein R represents an alkyl group, R2 represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom, and D represents anary-lene group. i 6.- A photographicsilver halide emulsion oon taming fromw2.5 110.25 rams per unit of silver halide formed from 1000 gramsof silver nitrate, of s. compound; selected from those represented by the following general formula:
wherein R. represents an alkyl group containing from '1' to 2 carbon atoms, R2 represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom, and D repre'sents'a phenylene group. I
'7. A photographic silver halide emulsion containing from 2.5 to 25 grams per unit of silver halideformed from 1000, gram lei-silver nitrate, of-a, oompoundseleoted from those represented by the following general formula:
C NH C ZH-BR:
wherein R2 represents a member selected from the group consisting of a hydrogen atom and D represents an arylene group.
8. A photographic silver halide emulsion containing from 2.5 to 25' grams per unit of silver halide formed from 1000 grams 'of silver nitrate, of a compound selected from those represented by the following general formula:
wherein R2 represents a member selected from the group consisting of a hydrogen atom and Drepresents an arylene group. 9. A photographic silver halide emulsion containingjrom 2.5 grams per unit to 25 grams per unit of silver halide formed from 1000 grams of silvernitrate of acompound selected from the group consisting of 2-a-mercaptopropionamidobenzthiazole, '2-'o.-mercaptopropionamido-6- ethoxybenzthiazole, 2-a-mercaptopropionamido- 6-methoxybenzthiazo1e, 6 Ch 1QI0-2-a-II1BICaptO propionamidobenzthiazole, "zfa mercaptobutyramidob'enz'thiazole, and alkali metal salts of said compounds.
. EDWARDiB. KNOTT.
PHILIP K. BROOKS.
References Cited in the file of'this patent UNITED STATES PATENTS Number Name Date 2,040,928 Engelmann May 19, 1936 2,051,145 Lubs et a1. Aug. 18, 1936 2,282,005 Sheppard et al'. May 5, 1942 2,311,103 Weyerts Feb. 16, 1943
Claims (1)
1. THE METHOD OF PREVENTING IMAGE DEGRADATION OF AN EXPOSED SILVER HALIDE EMULSION DURING PROCESSING, WHICH COMPRISES PERFORMING AT LEAST ONE OF THE STEPS OF DEVELOPING, FIXING, WASHING AND DRYING SAID EMULSION IN THE PRESENCE IN SAID EMULSION OF FROM 2.5 GRAMS TO 25 GRAMS PER UNIT OF SILVER HALIDE FORMED FROM 1000 GRAMS OF SILVER NITRATE, OF A COMPOUND SELECTED FROM THOSE REPRESENTED BY THE FOLLOWING GENERAL FORMULA:
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7421/51A GB708065A (en) | 1951-03-30 | 1951-03-30 | Improvements in the production of photographic images |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2657136A true US2657136A (en) | 1953-10-27 |
Family
ID=9832805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US253206A Expired - Lifetime US2657136A (en) | 1951-03-30 | 1951-10-25 | Photographic antiplumming agents and compositions containing them |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2657136A (en) |
| BE (1) | BE510333A (en) |
| FR (1) | FR1057981A (en) |
| GB (1) | GB708065A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2835581A (en) * | 1955-06-15 | 1958-05-20 | Eastman Kodak Co | Tetrazaindenes and photographic emulsions containing them |
| US2952687A (en) * | 1960-09-13 | Certain n- | ||
| US3305362A (en) * | 1962-03-08 | 1967-02-21 | Agfa Ag | Process for developing silver halide and compositions therefor |
| EP1192128A4 (en) * | 1999-06-15 | 2003-07-02 | Merck & Co Inc | Thiol derivative, metallo-beta-lactamase inhibitors |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE548727A (en) * | 1955-06-21 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2040928A (en) * | 1936-05-19 | |||
| US2051145A (en) * | 1931-05-06 | 1936-08-18 | Du Pont | Chlorinated aryl-thiazoles and process for their production |
| US2282005A (en) * | 1940-03-02 | 1942-05-05 | Eastman Kodak Co | Phenazine and naphthazine fog inhibitor for photographic emulsions |
| US2311103A (en) * | 1941-11-13 | 1943-02-16 | Eastman Kodak Co | Photographic silver halide emulsion |
-
0
- BE BE510333D patent/BE510333A/xx unknown
-
1951
- 1951-03-30 GB GB7421/51A patent/GB708065A/en not_active Expired
- 1951-10-25 US US253206A patent/US2657136A/en not_active Expired - Lifetime
-
1952
- 1952-03-29 FR FR1057981D patent/FR1057981A/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2040928A (en) * | 1936-05-19 | |||
| US2051145A (en) * | 1931-05-06 | 1936-08-18 | Du Pont | Chlorinated aryl-thiazoles and process for their production |
| US2282005A (en) * | 1940-03-02 | 1942-05-05 | Eastman Kodak Co | Phenazine and naphthazine fog inhibitor for photographic emulsions |
| US2311103A (en) * | 1941-11-13 | 1943-02-16 | Eastman Kodak Co | Photographic silver halide emulsion |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2952687A (en) * | 1960-09-13 | Certain n- | ||
| US2835581A (en) * | 1955-06-15 | 1958-05-20 | Eastman Kodak Co | Tetrazaindenes and photographic emulsions containing them |
| US3305362A (en) * | 1962-03-08 | 1967-02-21 | Agfa Ag | Process for developing silver halide and compositions therefor |
| EP1192128A4 (en) * | 1999-06-15 | 2003-07-02 | Merck & Co Inc | Thiol derivative, metallo-beta-lactamase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| GB708065A (en) | 1954-04-28 |
| FR1057981A (en) | 1954-03-12 |
| BE510333A (en) |
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