US2855301A - 2-mercaptooxazolines as developer retarders - Google Patents
2-mercaptooxazolines as developer retarders Download PDFInfo
- Publication number
- US2855301A US2855301A US621213A US62121356A US2855301A US 2855301 A US2855301 A US 2855301A US 621213 A US621213 A US 621213A US 62121356 A US62121356 A US 62121356A US 2855301 A US2855301 A US 2855301A
- Authority
- US
- United States
- Prior art keywords
- developer
- mercaptooxazoline
- development
- fog
- net
- 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
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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/305—Additives other than developers
Definitions
- developer retarders and inhibitors have been known for many years.
- 6-nitrobenzimida'zole in an effort to slow down development, permit prolonged development without excessive fog, increase contrast, and minimize reciprocity law failure (R. L. F.) of sensitive photographic products is well known.
- S-mercapto-l-phenyltetrazole has been proposed as a developer retarder specifically for controlling development fog.
- R, R R and R are hydrogen, an aliphatic ethyl, etc., alkylsulfonic acid, i. e., ethylsulfonic acid, propylsulfonic acid, etc., a cycloaliphatic radical, i. e., bornyl, camphonyl, iononyl, etc., an aromatic radical, i. e., phenyl, chlorophenyl, nitrophenyl, tolyl, hydroxyphenyl, napthyl, hydroxynapthyl, etc., heterocyclic, i.
- R, R R and R have the values given above with carbon disulfide in alkaline solution to form a dithiocarbamic which is then esterified with ethyl chloroformate. The resulting unstable dithiocarbamic ester is heated to form the Z-mercaptooxazolines.
- Z-mercaptooxazolines contemplated for use herein are not only recommended by their possession of the aforesaid characteristics, but in addition by virtue of the fact that they are relatively inexpensive and can be used in minimum amounts as compared to other developer retarders.
- the Z-mercaptooxazolines may be employed effectively either in the photographic developer or in a pre-bath used subsequent to exposure but prior to development. It is apparent that where the developer retarder is used in a pre-bath, its effect is manifested in the developing step.
- the quantity of the compound employed will be dictated by the specific end desired as subsequently indicated but in general will range from 0.79 mg. to mgs. per liter of developer.
- the gradient values were taken at maximum gradient of the SEIISltOIIlCtI'lC' curve.
- the speed values were taken at net densities above fog, and are expressed in arbitrary units.
- the net maximum density values are derived from total maximum density which has been corrected for both fog density and base density.
- EXAMPLE II High speed negative film was exposed in a time scale sensitometer and then developed in a hydroquinone-metol metaborate developer for times ranging from 3 to 30 minutes. Similar films were developed in the same type developer containing Z-mercaptooxazoline in concentrations of 20 mgs. per liter and 60 mgs. per liter. Sensitometric characteristics observed are given in Table IV.
- EXAMPLE III 'Table V shows the developer retarder and development fog inhibitor properties of 5-methyl-2-mercaptooxazoline. This table shows the sensitometr'ic characteristics of the film used when developed as in Example I in the developer which contains 5-methyl-2-mercaptooxazoline in concentrations between 0.79 mg. per liter and 100 mgs. per liter.
- the 5-methyl-Z-mercaptooxazoline used in this example was prepared as follows:
- EXAMPLE IV High speed negative film was developed in a developer as in Example II, which contained S-methyI-Z-mercaptooxazoline in concentrations from 3 mgs. per liter to 60 mgs. per liter. Sensitometric characteristics observed are given in Table VI.
- EXAMPLE v The sensitometric characteristics of another Z-mercaptooxazoline, namely 4-ethyl-Z-mercaptooxazoline, are given in Table VII. It was tested with the photographic materials and developer of Example I in a range of concentrations between 0.79 mg. per liter and mgs, per liter of the developer.
- the 4-ethyl-2-mercaptooxazoline used in this experiment was prepared from Z-amino-l-butanol by the method described in Example III.
- Reciprocity law failure activity of Z-mercaptooxazalines The data for R. L. F. are given in Table IX. In this table concentration is expressed in mgs. of compound per liter of developer. Reciprocity law failure is the maximum variation in speed over a range of exposure times from 1 second to 40 hours. Speed and R. L. F. are measured at net density 0.4. The data in the table represent a simultaneous comparison of the results obtained with the mercaptooxazolines on one hand and 6- nitrobenzimidazole on the other.
- a photographlc developer for silver-halide compris- 65 mg a silver-halide developer and as a developer retarder 1 31 52 70 0 a Z-mercaptooxazolme of the following general formula: 2 49 16 1. 14 1. 41 0 4 49 14 1. 64 1. 77 0 R1 R1 6 57 17 2. 04 1. 97 0 10 58 20 2.00 1. 96 0 RC-GRa 16 64 24 2. 12 2. 16 o 7 6 265 84 2. 95 3. 27 11 N 10 350 103 3.00 3. 37 18 16 620 136 2. 50 3. 17 46 (J 6 255 86 3. 04 3. 14 12 10 310 106 2. 86 3. 17 27 SH 16 610 2. 44 2. 80 84 75 wherein R, R R and R are selected from the class 7 consisting of hydrogen, aliphatic, aromatic and heterocyclic radicals.
- An alkaline photographic developer for silver-halide comprising a silver-halide developer and a Z-mercaptooxazoline of the following formula:
- An alkaline photographic developer for silver-halide comprising a silver-halide developer and a Z-mercaptooxazoline of the following formula:
- R, R R and R are selected from the class consisting of hydrogen, aliphatic, aromatic, and heterocyclic radicals.
- R, R R and R are selected from the class consisting of hydrogen, aliphatic, aromatic, and heterocyclic radicals and then developing said silver-halide emulsion in an alkaline developer containing a developing agent for said emulsion.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DENDAT1071480D DE1071480B (fr) | 1956-11-09 | ||
US621213A US2855301A (en) | 1956-11-09 | 1956-11-09 | 2-mercaptooxazolines as developer retarders |
GB33577/57A GB838557A (en) | 1956-11-09 | 1957-10-28 | 2-mercaptooxazolines as developer retarders |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US621213A US2855301A (en) | 1956-11-09 | 1956-11-09 | 2-mercaptooxazolines as developer retarders |
Publications (1)
Publication Number | Publication Date |
---|---|
US2855301A true US2855301A (en) | 1958-10-07 |
Family
ID=24489221
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US621213A Expired - Lifetime US2855301A (en) | 1956-11-09 | 1956-11-09 | 2-mercaptooxazolines as developer retarders |
Country Status (3)
Country | Link |
---|---|
US (1) | US2855301A (fr) |
DE (1) | DE1071480B (fr) |
GB (1) | GB838557A (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2987396A (en) * | 1958-12-29 | 1961-06-06 | Eastman Kodak Co | Photographic silver halide diffusion transfer process |
US3068099A (en) * | 1961-02-01 | 1962-12-11 | Gen Aniline & Film Corp | Photographic silver halide emulsions containing thioethers of saturated oxygen heterocycles as stabilizers and antifoggants |
US4273862A (en) * | 1977-06-11 | 1981-06-16 | Mitsubishi Paper Mills, Ltd. | Direct-positive silver halide photographic sensitive materials |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2614925A (en) * | 1949-12-20 | 1952-10-21 | Eastman Kodak Co | Mercapto azoles in developer for mixed grain photographic process |
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0
- DE DENDAT1071480D patent/DE1071480B/de active Pending
-
1956
- 1956-11-09 US US621213A patent/US2855301A/en not_active Expired - Lifetime
-
1957
- 1957-10-28 GB GB33577/57A patent/GB838557A/en not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2614925A (en) * | 1949-12-20 | 1952-10-21 | Eastman Kodak Co | Mercapto azoles in developer for mixed grain photographic process |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2987396A (en) * | 1958-12-29 | 1961-06-06 | Eastman Kodak Co | Photographic silver halide diffusion transfer process |
US3068099A (en) * | 1961-02-01 | 1962-12-11 | Gen Aniline & Film Corp | Photographic silver halide emulsions containing thioethers of saturated oxygen heterocycles as stabilizers and antifoggants |
US4273862A (en) * | 1977-06-11 | 1981-06-16 | Mitsubishi Paper Mills, Ltd. | Direct-positive silver halide photographic sensitive materials |
Also Published As
Publication number | Publication date |
---|---|
DE1071480B (fr) | |
GB838557A (en) | 1960-06-22 |
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