US3068100A - N-acylhomocysteine thiolactone stabilizers for photographic silver halide emulsions - Google Patents
N-acylhomocysteine thiolactone stabilizers for photographic silver halide emulsions Download PDFInfo
- Publication number
- US3068100A US3068100A US68653A US6865360A US3068100A US 3068100 A US3068100 A US 3068100A US 68653 A US68653 A US 68653A US 6865360 A US6865360 A US 6865360A US 3068100 A US3068100 A US 3068100A
- Authority
- US
- United States
- Prior art keywords
- emulsion
- silver halide
- thiolactone
- stabilizers
- compound
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—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
- G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
- G03C1/346—Organic derivatives of bivalent sulfur, selenium or tellurium
Definitions
- This invention relates to photographic materials and to methods of preparing them. More particularly, this invention relates to light-sensitive silver halide emulsions cqntaining as a stabilizing and antifogging agent an N- acyl DL-homocysteine thiolactone.
- an object of this invention to produce Ea light-sensitive emulsion which is fast, stable, has a :reduced tendency to fog and has good contrast.
- a further object of this invention resides in a lightsensitive emulsion which contains a compound which stabilizes the emulsion against fogging and at the same time does not materially reduce the speed and/or the contrast of the emulsion.
- N-acyl DL-homocysteine thiolactones when added to a light-sensitive silver halide emulsion, stabilize and inhibit the fogging of the emulsion.
- the N-acyl DL-homocysteine thiolactones may be represented by the following formula:
- N-acetyl DL-homocysteine thiolactone N-proplonyl DL-homocysteine thlolactone duction may be added as a ripening final or as a coating final.”
- a ripening final When added as a ripening final,” they are added during the ripening or sensitivity increasing stage of the emulsion-making process.
- Such addition may be made before, during or after the addi-' tion of the soluble silver salt to the soluble halide in the presence of a suitable colloid such as gelatin, polyvinyl alcohol, solubilized casein or albumin which may be used' as the carrier material.
- the antifogging agent of my invention When added as a coating final, the antifogging agent of my invention is added to the emulsion just prior to coating it on a suitable support such as glass, paper or film at a time when the emulsion has nearly attained its maximum sensitivity.
- a suitable support such as glass, paper or film
- the antifoggants of my invention are preferably added to the emulsion in an amount ranging from 0.1 milligram to 60 milligrams per 0.6 mol of silver halide; and when used as a coating final, they are preferably added in an amount ranging from 10 milligrams to 300 milligrams per 0.6 mol of silver halide.
- the optimum amount to be added depends primarily on the type of emulsion and should be determined individually in each case.
- the stabilizers and antifoggants of my invention may also be used in combination with known antifoggants and stabilizers; the antifoggants of my invention can also be used in combination with sensitizers such as sulfur, metal and reduction sensitizers as well as with speed-increasing agents and accelerators such as the reaction products of long-chain alcohols and ethylene oxide (see United States Patent 1,907,578) and their derivatives.
- sensitizers such as sulfur, metal and reduction sensitizers
- speed-increasing agents and accelerators such as the reaction products of long-chain alcohols and ethylene oxide (see United States Patent 1,907,578) and their derivatives.
- novel antifoggants of my invention may be used with various types of photographic emulsions such as non-sensitized orthochromatic, panchromatic and X-ray emulsions, paper emulsions and color emulsions.
- Example I A silver halide emulsion in gelatin containing 2 percent silver iodide and 98 percent silver bromide was prepared in a conventional manner and brought up to its maximum light sensitivity. It was then readied for coating by adding finals such as sensitizing dyes and hardening agents. A 0.1 percent solution of N-acetyl DL-homocysteine thiolactone prepared as described above was added in varying amounts to samples of the emulsion as an antifoggant and stabilizer. Each emulsion sample contained about 0.6 mol of silver halide. The so prepared emulsion samples were coated on a suitable cellulose ester base and dried. Samples of these film coatings were then exposed in a Type IIB Sensitometer and developed in a developer of the following composition:
- Example II The procedure followed was identical to Example I except that in place of N-acetyl DL-homocysteine thiolactone the compound used was N-propionyl DL-homocysteine thioiactone prepared in an analogous manner except that propionic anhydride was used in place of acetic anhydride.
- Example III The procedure followed was identical to Example I but in place of used the compound N-butyryl DL-homocysteine thiolac tone which had been prepared by using butyric anhydride in place of acetic anhydride.
- Example IV Several examples of a conventional film were exposed in a Type IIB Sensitometer and then divided into two groups. One group of samples was developed for twelve minutes at 68 F. in a standard metol hydroquinone developer as described in Example I. The second group of samples was developed for the same length of time and at the same temperature as the first group in a metol hydroquinone developer which had been prepared by adding to the developer described in Example I 10 mgs. of N-acetyl DL-homocysteine thiolactone per liter of developer. It was found that both sets of samples had the same relative speed of 100. However, the samples developed in the control developer showed a fog of .30 whereas the strips which had been developed in the presence of the antifoggant showed a fog of 0.20.
- N-acetyl DL-homocysteine thiolactone was 4 Example V
- One kilo of a silver halide emulsion in gelatin contain ing 4 percent silver iodide and 96 percent silver bromide was coated on film base in a manner known to the art. After the coating was performed, an aqueous gelatin solution containing 20 grams of gelatin per liter and 1.2 grams of the N-acetyl DL-homocysteine thiolactone of Example I was coated thereon as an antiabrasion layer. After drying, film samples were exposed and processed as described in Example I.
- the samples described exhibited a relative speed of 100 with a fog of .12 as compared with a type coating of the same emulsion having an antiabrasion layer similar to that described above but lacking the antifogging additive and having a speed of 100 and a fog of .20.
- R is a lower alkyl group of from 1 to 3 carbon.
- a light-sensitive silver halide emulsion as recited in claim 1 containing a sensitizing dye.
- a light-sensitive silver halide emulsion as recited in claim 1 containing the reaction product of a long chain alcohol and an ethylene oxide as an accelerator.
- a light-sensitive photographic element comprising a base and a coating of gelatino silver halide emulsion; thereon said emulsion containing as an antifogging andstabilizing agent a compound having the following general formula:
- R is a member selected from the group consisting of methyl, ethyl and propyl.
- a process according to claim 12 wherein said corn i pound is N-aectyl DL-homocysteine thiolactone.
- a process of forming a photographic emulsion having a reduced tendency to fog which comprises forming the emulsion, ripening the emulsion and during said ripening adding thereto a compound having the following general formula:
- R is an alkyl group of from 1 to 3 carbon atoms.
- a process according to claim 14 wherein said compound is N-acetyl DL-homocysteine thiolactone.
- R represents a member selected from the group consisting of methyl, ethyl and propyl radicals.
- a process according to claim 16 wherein said antijoggant is N-acetyl DL-homocysteine thiolactone.
- a process according to claim 16 wherein said anti foggant is N-propionyl DL-homocysteine thiolactone.
- a photographic developer solution comprising an organic developing agent, an alkali, an alkali metal sulfite, an alkali metal bromide and as an antifoggant, in an antifogging amount, a compound having the following general formula:
Landscapes
- 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)
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE610270D BE610270A (de) | 1960-11-14 | ||
US68653A US3068100A (en) | 1960-11-14 | 1960-11-14 | N-acylhomocysteine thiolactone stabilizers for photographic silver halide emulsions |
GB39492/61A GB925115A (en) | 1960-11-14 | 1961-11-03 | Stabilization of photographic silver halide emulsions |
FR878773A FR1315070A (fr) | 1960-11-14 | 1961-11-13 | émulsions photographiques stabilisées d'halogénure d'argent et leur procédé de préparation |
DEG33571A DE1177001B (de) | 1960-11-14 | 1961-11-14 | Verfahren zur Verhuetung der Schleier-bildung bei photographischen Materialien und photographisches Material hierfuer |
CH1323161A CH435972A (de) | 1960-11-14 | 1961-11-14 | Verwendung einer chemischen Verbindung als Antischleiermittel |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US68653A US3068100A (en) | 1960-11-14 | 1960-11-14 | N-acylhomocysteine thiolactone stabilizers for photographic silver halide emulsions |
Publications (1)
Publication Number | Publication Date |
---|---|
US3068100A true US3068100A (en) | 1962-12-11 |
Family
ID=22083898
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US68653A Expired - Lifetime US3068100A (en) | 1960-11-14 | 1960-11-14 | N-acylhomocysteine thiolactone stabilizers for photographic silver halide emulsions |
Country Status (6)
Country | Link |
---|---|
US (1) | US3068100A (de) |
BE (1) | BE610270A (de) |
CH (1) | CH435972A (de) |
DE (1) | DE1177001B (de) |
FR (1) | FR1315070A (de) |
GB (1) | GB925115A (de) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3201243A (en) * | 1962-10-18 | 1965-08-17 | Eastman Kodak Co | Method of inhibiting discoloration of color photographic layers containing dye images and resulting photographic products |
US4142895A (en) * | 1977-01-12 | 1979-03-06 | Agfa Gevaert Aktiengesellschaft | Photographic color developer composition |
US4155764A (en) * | 1976-05-21 | 1979-05-22 | Agfa-Gevaert, A.G. | Photographic color developer composition |
US4230796A (en) * | 1978-01-18 | 1980-10-28 | E. I. Du Pont De Nemours And Company | High speed lithographic film element |
US4243748A (en) * | 1979-05-29 | 1981-01-06 | E. I. Du Pont De Nemours And Company | Light-sensitive silver halide reproduction material |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2502153A1 (fr) * | 1981-03-19 | 1982-09-24 | Rech Pharmaceutiq Medicale | Acides (2-oxo-3-tetrahydrothienylcarbamoyl)-alkylthio) acetiques, leurs sels et leurs esters, leur procede de preparation et les compositions pharmaceutiques en contenant |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2824001A (en) * | 1956-01-16 | 1958-02-18 | Eastman Kodak Co | Stabilized photographic silver halide emulsions |
US2870015A (en) * | 1957-03-08 | 1959-01-20 | Eastman Kodak Co | Stabilized photographic silver halide emulsions |
US2939789A (en) * | 1958-06-06 | 1960-06-07 | Gen Aniline & Film Corp | Fog reduction in photographic silver halide emulsions |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE957183C (de) * | 1953-07-01 | 1957-01-31 | Eastman Kodak Co | Stabilisiertes photographisches Material |
-
0
- BE BE610270D patent/BE610270A/xx unknown
-
1960
- 1960-11-14 US US68653A patent/US3068100A/en not_active Expired - Lifetime
-
1961
- 1961-11-03 GB GB39492/61A patent/GB925115A/en not_active Expired
- 1961-11-13 FR FR878773A patent/FR1315070A/fr not_active Expired
- 1961-11-14 CH CH1323161A patent/CH435972A/de unknown
- 1961-11-14 DE DEG33571A patent/DE1177001B/de active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2824001A (en) * | 1956-01-16 | 1958-02-18 | Eastman Kodak Co | Stabilized photographic silver halide emulsions |
US2870015A (en) * | 1957-03-08 | 1959-01-20 | Eastman Kodak Co | Stabilized photographic silver halide emulsions |
US2939789A (en) * | 1958-06-06 | 1960-06-07 | Gen Aniline & Film Corp | Fog reduction in photographic silver halide emulsions |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3201243A (en) * | 1962-10-18 | 1965-08-17 | Eastman Kodak Co | Method of inhibiting discoloration of color photographic layers containing dye images and resulting photographic products |
US4155764A (en) * | 1976-05-21 | 1979-05-22 | Agfa-Gevaert, A.G. | Photographic color developer composition |
US4142895A (en) * | 1977-01-12 | 1979-03-06 | Agfa Gevaert Aktiengesellschaft | Photographic color developer composition |
US4230796A (en) * | 1978-01-18 | 1980-10-28 | E. I. Du Pont De Nemours And Company | High speed lithographic film element |
US4243748A (en) * | 1979-05-29 | 1981-01-06 | E. I. Du Pont De Nemours And Company | Light-sensitive silver halide reproduction material |
Also Published As
Publication number | Publication date |
---|---|
DE1177001B (de) | 1964-08-27 |
CH435972A (de) | 1967-05-15 |
BE610270A (de) | |
FR1315070A (fr) | 1963-01-18 |
GB925115A (en) | 1963-05-01 |
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