US2915395A - Antifogging agents for light sensitive paper emulsions - Google Patents
Antifogging agents for light sensitive paper emulsions Download PDFInfo
- Publication number
- US2915395A US2915395A US640428A US64042857A US2915395A US 2915395 A US2915395 A US 2915395A US 640428 A US640428 A US 640428A US 64042857 A US64042857 A US 64042857A US 2915395 A US2915395 A US 2915395A
- Authority
- US
- United States
- Prior art keywords
- nitrobenzotriazole
- emulsion
- light sensitive
- emulsions
- sensitive paper
- 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
- 239000000839 emulsion Substances 0.000 title claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- AOCDQWRMYHJTMY-UHFFFAOYSA-N 5-nitro-2h-benzotriazole Chemical compound C1=C([N+](=O)[O-])C=CC2=NNN=C21 AOCDQWRMYHJTMY-UHFFFAOYSA-N 0.000 claims description 7
- -1 SILVER HALIDE Chemical class 0.000 claims description 5
- SDGOKYAKHWEFKN-UHFFFAOYSA-N [3-(carbamoylamino)-1h-1,2,4-triazol-5-yl]urea Chemical compound NC(=O)NC1=NNC(NC(N)=O)=N1 SDGOKYAKHWEFKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 239000004332 silver Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 10
- 230000018109 developmental process Effects 0.000 description 9
- 108010010803 Gelatin Proteins 0.000 description 8
- 229920000159 gelatin Polymers 0.000 description 8
- 239000008273 gelatin Substances 0.000 description 8
- 235000019322 gelatine Nutrition 0.000 description 8
- 235000011852 gelatine desserts Nutrition 0.000 description 8
- 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 7
- 229910001961 silver nitrate Inorganic materials 0.000 description 5
- 239000002344 surface layer Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
Images
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
Definitions
- the present invention relates to photographic paper emulsions and more particularly to such emulsions containing S-nitrobenzotriazole as a stabilizer therefor.
- a stabilizer having the ability to act as an antifogging agent for the emulsion.
- One type of such agent recommended for this purpose is a heterocyclic mercapto compound. It has been ascertained, however, that this type of compound, while it is capable of operating as an antifogging agent, has the unfortunate characteristic of causing the image produced in the paper to fade on aging and to assume a yellow tone. There is, therefore, a decided need for stabilizers which not only are antifoggants for paper emulsions but, at the same time reduce the tendency of the image produced in the emulsion to fade or change color on aging.
- S-nitrobenzotriazole which may be incorporated in the emulsion as a coating final.
- a further improvement in fog resistance is obtained when overcoating a paper emulsion containing the S-nitrobenzotriazole with a gelatin surface layer containing the silver salt of said S-nitrobenzotriazole.
- antifogging agents normally tend to restrict the rate of development of the emulsion in which they are located. This is equally true of the 5- nitrobenzotriazole which we find so satisfactory as an antifogging agent.
- a further and important discovery, the use of which is contemplated herein, involves the employment in the emulsion with the S-nitrobenzotriazole, of 3,5-diureido- 1,2,4-triazole to overcome the slow development rate im parted to the emulsion by the S-nitrobenzotriazole.
- Said diureido compound may be used as such or in the form of its disulfonate.
- Photographic paper emulsions containing S-nitrobenzotriazole as an antifogging agent such emulsions overcoated with a gelatin surface layer containing the silver salt of S-nitrobenzotriazole, and such emulsions containing the aforementioned diureido-triazoles as development accelerators, constitute the purposes and objects of our invention.
- the S-nitrobenzotriazole is generally employed in the emulsion in a quantity of 100 to 500 mgs. per 100 gms. of silver nitrate. This compound is added to the emulsion just prior to coating in a solution of methanol or ethanol or of water and an organic solvent miscible with water such as Cellosolve. Typically, we have employed alcoholic solutions of the stabilizer. The emulsion, following the addition of the S-nitrobenzotriazole, is coated and dried.
- R is an alkali metal such as sodium, potassium or the like.
- the aforesaid diureido compounds are added at the same time as the S-nitrobenzotriazole and in a concentration of about to 500 mgs. per 100 gms. of silver nitrate. Said compounds operate to improve the development rate over and above the acceptable rate with the S-nitrobenzotriazole alone.
- the S-nitrobenzotriazole in and of itself is an excellent antifogging agent. Nevertheless, a further improvement in fog resistance is realized if an emulsion containing said agent is overcoated with a gelatin surface layer containing the silver salt of 5-nitrobenzotriazole in a concentration ranging from 20 to 50 mgs. per kilogram of gelatin.
- Example I A chlor-bromide paper emulsion is prepared in the usual way and just prior to coating, there are added thereto 250 mgs. per 100 gms. of silver nitrate of 5- nitrobenzotriazole in alcohol. The emulsion is coated on a paper base and dried.
- the dried emulsion is then overcoated with a gelatin surface layer containing an alcoholic solution of the silver salt of S-nitrobenzotriazole in a concentration of 30 mgs. per kilogram of gelatin.
- the resulting light sensitive paper emulsion will be found to be fog free and to yield, upon exposure and development, a silver image which will not yellow or fade on aging.
- Example II The procedure is the same as in Example I excepting that 3,S-diureido-1,2,4-triazole is added to the emulsion with the S-nitrobenzotriazole, the diureido compound being added in a concentration of 300 mgs. per 100 gms. of silver nitrate.
- dialkali metal sulfonates of the latter compound may be obtained by reacting the free 3,5-diureido-l,2,4- triazole with chlor-sulfonic acid in the presence of an acid binding agent such as pyridine, trimethylamine and the like.
- a light sensitive photographic paper comprising a base coated with a silver halide emulsion containing 5- nitrobenzotriazole as an antifogging agent and a compound selected from the class consisting of 3,5-diureido- 1,2,4-triazole and its diallcali metal su l fonate as a development accelerator;
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- 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)
Description
De 1, 19 s. P. POPECK ETAL 2,915,395
ANTIFOGGING AGENTS FOR LIGHT SENSITIVE PAPER EMULSIONS Filed Feb. 15, 1957 OVERCOATING OF GELATIN CONTAINING SILVER SALT OF 5-NITROBENZOTRIAZOLE SILVER HALIDE EMULSION CONTAINING 5-N|TROBENZOTRIAZOLE AND 3,5-DIUREIDO-I,2,4-TRIAZOLE PAPER BASE STANLEY P. POPECK JOSEPH RSOTTYSIAK mmvrons United States Patent ANTIFOGGIN G AGENTS FOR LIGHT SENSITIVE PAPER EMULSIONS Stanley P. Popeck and Joseph R. Sottysiak, Binghamton,
ll.Y., assignors to General Aniline & Film Corporation, New York, N.Y., a corporation of Delaware Application February 15, 1957, Serial No. 640,428
5 Claims. (CI. 96-85) The present invention relates to photographic paper emulsions and more particularly to such emulsions containing S-nitrobenzotriazole as a stabilizer therefor.
It is customary practice to incorporate in photographic paper emulsions, such as those from silver chloride, silver bromide, silver chlorbromide and the like, a stabilizer having the ability to act as an antifogging agent for the emulsion. One type of such agent recommended for this purpose is a heterocyclic mercapto compound. It has been ascertained, however, that this type of compound, while it is capable of operating as an antifogging agent, has the unfortunate characteristic of causing the image produced in the paper to fade on aging and to assume a yellow tone. There is, therefore, a decided need for stabilizers which not only are antifoggants for paper emulsions but, at the same time reduce the tendency of the image produced in the emulsion to fade or change color on aging.
We have discovered that an agent meeting these characteristics is S-nitrobenzotriazole which may be incorporated in the emulsion as a coating final. We have also discovered that a further improvement in fog resistance is obtained when overcoating a paper emulsion containing the S-nitrobenzotriazole with a gelatin surface layer containing the silver salt of said S-nitrobenzotriazole.
It is recognized that antifogging agents normally tend to restrict the rate of development of the emulsion in which they are located. This is equally true of the 5- nitrobenzotriazole which we find so satisfactory as an antifogging agent.
A further and important discovery, the use of which is contemplated herein, involves the employment in the emulsion with the S-nitrobenzotriazole, of 3,5-diureido- 1,2,4-triazole to overcome the slow development rate im parted to the emulsion by the S-nitrobenzotriazole. Said diureido compound may be used as such or in the form of its disulfonate.
Photographic paper emulsions containing S-nitrobenzotriazole as an antifogging agent, such emulsions overcoated with a gelatin surface layer containing the silver salt of S-nitrobenzotriazole, and such emulsions containing the aforementioned diureido-triazoles as development accelerators, constitute the purposes and objects of our invention.
The S-nitrobenzotriazole is generally employed in the emulsion in a quantity of 100 to 500 mgs. per 100 gms. of silver nitrate. This compound is added to the emulsion just prior to coating in a solution of methanol or ethanol or of water and an organic solvent miscible with water such as Cellosolve. Typically, we have employed alcoholic solutions of the stabilizer. The emulsion, following the addition of the S-nitrobenzotriazole, is coated and dried.
To improve the rate of development of the emulsions so coated, it is recommended that there also be added to the emulsion, either 3,5-diureido-1,2,4-triazole or a water soluble disulfonate thereof. These compounds have the following structural formulae:
2,915,395 Patented Dec. 1, 1959 and H 0 H N- H 0 H ROME-(Lil (labial-Boa. N H
wherein R is an alkali metal such as sodium, potassium or the like.
The aforesaid diureido compounds are added at the same time as the S-nitrobenzotriazole and in a concentration of about to 500 mgs. per 100 gms. of silver nitrate. Said compounds operate to improve the development rate over and above the acceptable rate with the S-nitrobenzotriazole alone.
The S-nitrobenzotriazole in and of itself is an excellent antifogging agent. Nevertheless, a further improvement in fog resistance is realized if an emulsion containing said agent is overcoated with a gelatin surface layer containing the silver salt of 5-nitrobenzotriazole in a concentration ranging from 20 to 50 mgs. per kilogram of gelatin.
The invention is further illustrated by the accompanying, self-explanatory drawing and examples in which the parts are by weight.
Example I A chlor-bromide paper emulsion is prepared in the usual way and just prior to coating, there are added thereto 250 mgs. per 100 gms. of silver nitrate of 5- nitrobenzotriazole in alcohol. The emulsion is coated on a paper base and dried.
The dried emulsion is then overcoated with a gelatin surface layer containing an alcoholic solution of the silver salt of S-nitrobenzotriazole in a concentration of 30 mgs. per kilogram of gelatin.
The resulting light sensitive paper emulsion will be found to be fog free and to yield, upon exposure and development, a silver image which will not yellow or fade on aging.
Example II The procedure is the same as in Example I excepting that 3,S-diureido-1,2,4-triazole is added to the emulsion with the S-nitrobenzotriazole, the diureido compound being added in a concentration of 300 mgs. per 100 gms. of silver nitrate.
An emulsion is thus obtained which not only has the characteristics of those of Example I but, in addition, has a development rate over and above the acceptable rate with 5-nitrobenzotriazole alone.
S-nitrobenzotriazole which has the following constitu' tion N No,- N%
and 3,5-diureido-1,2,4-triazole are known compounds.
The dialkali metal sulfonates of the latter compound may be obtained by reacting the free 3,5-diureido-l,2,4- triazole with chlor-sulfonic acid in the presence of an acid binding agent such as pyridine, trimethylamine and the like.
Modifications of the invention will occur to persons skilled in the art and we, therefore, do not intend to be limited in the patent granted except as necessitated by the appended claims.
We claim:
- 1. A light sensitive photographic paper comprising a base coated with a silver halide emulsion containing 5- nitrobenzotriazole as an antifogging agent and a compound selected from the class consisting of 3,5-diureido- 1,2,4-triazole and its diallcali metal su l fonate as a development accelerator;
2. The article as defined in claim 1 wherein the anti fogging agent and the development accelerator are present in a concentration of from 100 to 500 mgs. per 100 gms. of silver nitrate.
3. The article as defined in claim 1 wherein the silver halide emulsion is overcoated with a gelatin surface layer containing the silver salt of 5 -nitrobenzotriazole.
51. The article as defined in claim 3 wherein the silver salt of the S-nitrobenzotriazole is present in a concentra- References Cited in the file of this patent UNITED STATES PATENTS 2,656,271 Neugebauer et al Oct. 20, 19 53 FOREIGN PATENTS 142,505 Australia Mar. 17, 1949 OTHER REFERENCES Beilstein: Handbuch de Organischen Chemie, pages 43-44, volume 26, Edwards Brothers Inc., Lithoprinters, Ann Arbor, Mich., 1944. (Copy in Sci. Libr.)
Claims (1)
1. A LIGHT SENSITIVE PHOTAGRAPHIC PAPER COMPRISING A BASE COATED WITH SILVER HALIDE EMULSION CONTAINING 5NITROBENZOTRIAZOLE AS AN ANTIFOGGING AGENT AND A COMPOUND SELECTED FROM THE CLASS CONSISTING OF 3,5-DIUREIDO1,2,4-TRIAZOLE AND ITS DIALKALI METAL SULFONATE AS A DEVELOPMENT ACCELERATOR.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US640428A US2915395A (en) | 1957-02-15 | 1957-02-15 | Antifogging agents for light sensitive paper emulsions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US640428A US2915395A (en) | 1957-02-15 | 1957-02-15 | Antifogging agents for light sensitive paper emulsions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2915395A true US2915395A (en) | 1959-12-01 |
Family
ID=24568196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US640428A Expired - Lifetime US2915395A (en) | 1957-02-15 | 1957-02-15 | Antifogging agents for light sensitive paper emulsions |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2915395A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3042521A (en) * | 1957-12-26 | 1962-07-03 | Gen Aniline & Film Corp | Antifoggants and stabilizers for photographic silver halide emulsion |
| US4093462A (en) * | 1976-11-11 | 1978-06-06 | Eastman Kodak Company | 2,5-Bis(secondary amino) oxa- and thiadiazole photographic developing agents |
| US4163669A (en) * | 1977-04-27 | 1979-08-07 | Mitsubishi Paper Mills, Ltd. | Multilayer silver halide color photographic material |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2656271A (en) * | 1949-10-24 | 1953-10-20 | Keuffel & Esser Co | Method of developing aged photosensitive material containing silver halide and a chromate |
-
1957
- 1957-02-15 US US640428A patent/US2915395A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2656271A (en) * | 1949-10-24 | 1953-10-20 | Keuffel & Esser Co | Method of developing aged photosensitive material containing silver halide and a chromate |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3042521A (en) * | 1957-12-26 | 1962-07-03 | Gen Aniline & Film Corp | Antifoggants and stabilizers for photographic silver halide emulsion |
| US4093462A (en) * | 1976-11-11 | 1978-06-06 | Eastman Kodak Company | 2,5-Bis(secondary amino) oxa- and thiadiazole photographic developing agents |
| US4163669A (en) * | 1977-04-27 | 1979-08-07 | Mitsubishi Paper Mills, Ltd. | Multilayer silver halide color photographic material |
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