US3082088A - Process for maintaining the clarity of photographic silver halide emulsions at relatively high developer temperatures - Google Patents
Process for maintaining the clarity of photographic silver halide emulsions at relatively high developer temperatures Download PDFInfo
- Publication number
- US3082088A US3082088A US81949A US8194961A US3082088A US 3082088 A US3082088 A US 3082088A US 81949 A US81949 A US 81949A US 8194961 A US8194961 A US 8194961A US 3082088 A US3082088 A US 3082088A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- relatively high
- clarity
- maintaining
- urea
- 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 25
- -1 silver halide Chemical class 0.000 title claims description 18
- 229910052709 silver Inorganic materials 0.000 title claims description 12
- 239000004332 silver Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title description 3
- 239000000463 material Substances 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 description 15
- 239000010410 layer Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- ZDWPBMJZDNXTPG-UHFFFAOYSA-N 2h-benzotriazol-4-amine Chemical class NC1=CC=CC2=C1NN=N2 ZDWPBMJZDNXTPG-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- NFYPOLVKXIHFAG-UHFFFAOYSA-N 1-(2h-benzotriazol-4-yl)-3-phenylurea Chemical compound C=1C=CC2=NNN=C2C=1NC(=O)NC1=CC=CC=C1 NFYPOLVKXIHFAG-UHFFFAOYSA-N 0.000 description 1
- POZVYOVYIZCFLB-UHFFFAOYSA-N 1-(2h-benzotriazol-5-yl)-3-phenylurea Chemical compound C1=CC2=NNN=C2C=C1NC(=O)NC1=CC=CC=C1 POZVYOVYIZCFLB-UHFFFAOYSA-N 0.000 description 1
- BDQNKCYCTYYMAA-UHFFFAOYSA-N 1-isocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1 BDQNKCYCTYYMAA-UHFFFAOYSA-N 0.000 description 1
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- XSFHICWNEBCMNN-UHFFFAOYSA-N 2h-benzotriazol-5-amine Chemical compound NC1=CC=C2NN=NC2=C1 XSFHICWNEBCMNN-UHFFFAOYSA-N 0.000 description 1
- CIJUXZAARBQNOH-UHFFFAOYSA-N 2h-benzotriazol-5-ylurea Chemical compound NC(=O)NC1=CC=C2NN=NC2=C1 CIJUXZAARBQNOH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- AHUJYJLGIDQWLB-UHFFFAOYSA-N n-(2h-benzotriazol-4-yl)benzamide Chemical compound C=1C=CC2=NNN=C2C=1NC(=O)C1=CC=CC=C1 AHUJYJLGIDQWLB-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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 invention is concerned with a process for improving the clarity of, photognaphic silver halide emulsions during development at relatively high temperatures.
- Photognaphiesilver halide emulsions have a tendency at relatively high developer temperatures to give a considerable degree of fogging which appreciably impairs the quality of the picture. Since relatively high developer temperatures frequentlycannot be avoided, because of unfiavorable climatic conditions, it has long been desired to prevent the formation of this development fog by adding suitable substances to thephotographic silver halide emulsion, to the photographic auxiliary layers, or to the processing baths.
- R represents an aliphatic radical with at least two carbon atoms, an aromatic or heterocyclic radical which in turn may be substituted
- X represents a simple chemical bond, an oxygen atom or an imino radical and in which the benzene nucleus may also carry other substituents.
- Suitable substances for this purpose that conform to the foregoing formula are acylated aminobenztriazoles, such as S-benzoylaniinobenztriazole, carbamic acid derivatives such as Scarbethoxyaminobenztriazole, S-carbophenoxyaminobenztriazole, 4-carbophenoxyaminobenztriazole, 4 carbophenoxyam-ino-6eaminobenztriazlole and urea derivatives of benztriazole, such as N-'ethyl-N-(5)- benztriazolyl urea, N-pheny1-N-(4)-benztriazolyl urea, N-phenyl-N-()-benztriazolyl urea, N-(4'-ethoxyphenyl) N-(5)-benztriazolyl urea, N-(3-ch1orphenyl)-N- (5 -benztriazolyl urea, N- 4'-chlorphenyl) N-(5
- the acylated aminobenztriazoles are obtained by reac- Sttes Ptent lice H G CH3 N S H 02
- the outstanding efficacy of the substances according to the invention is apparent from the following table, which reproduces the fog values of a silver bromide emulsion according to Bios Final Report No. 252, which emulsion had been cast with and without addition of aminobenztriazole derivatives, after development for 4 minutes at 30 C.
- N-phenyl-N'-(4) -benztriazolyl urea 0.009 With N-phenyl-N'-(5)-benztriazolyl urea 0.015 With N (4-ethoxyphenyl)-N'-(5 )-benztriazolyl urea 0.015 With N-( 3-chlorphenyl -N-( 5 -benztriazolyl urea 0.017 With N-(4'-chlorpheny-l) -N'-(5 -benztriazolyl urea, 0.009 With S-benzoylaminobenztriazole (Example 1) 0.038 With S-carbophenoxyaminobenztriazole 0.017 With 4carbophenoxyaminobenztriazole 0.033 With 4 carbophenoxyarnino-flaminobenztriazole 0.027 With 4-benzoylaminobenztriazole 0.041 With 5-carboethoxyaminobenztriazole 0.037
- N-phenyl-N'-(5)-benztriaziolyl urea is added to a protective layer, the fog value after development for 4 minutes at 30 C. is 0.045, whereas the fog value without adding the stabilizer increases to 0.195.
- the emulsion used for this test was the same as mentioned above but this batch was very susceptible to fog formation.
- the substances according to the invention may be used in quantities from 5 to 250 mg. per liter of emulsion. 1 liter of emulsion contains approximately 30 g. of silver halide.
- 'Ihe substances according to the invention are suitable for reducing the fogging of silver chloride, silver bromochloride and silver bromide emulsions, and the maximum eiiect is produced with silver bnomide-ammonia emulsions.
- the emulsions may contain up to 5 percent silver iodide.
- Example 1 A silver bromide emulsion containing g. of AgBr to 3 liters has added thereto 8 cc. per liter of a 1% solution of the compound After adding the other conventional hardening agents, the emulsion is cast on to paper.
- the fog value with and without addition of stabilizer, after 4 minutes development at 30 C., are set out in the foregoing table. Development is carried out in a conventional metol-hydroquinone developer which is made alkaline with soda.
- Example 2 A silver bromochloride emulsion containing about 35 g. of AgBr and 70 g. of AgCl to three liters has added thereto, 3 cc. per liter of a 1 percent solution of the compound:
- the fog value after development for 4 minutes is 0.015 whereas it is 0.124 when no stabilizer has been added.
- Example 3 The stabilizer of the formula was prepared as follows:
- Example 4 The stabilizer of the formula velopment was accomplished as described in the foregoing example. After 4 minutes developing at 30 C. the fog value without addition of stabilizer was 0.113 while in the presence of the stabilizer of the above-mentioned formula the fog value was only 0.076.
- Example 5 The stabilizer of the formula H o d NH (3 NH 2 I N H2C ⁇ /CH2 s O: H
- Example 4 was prepared by reaction of cyclo-tetra-methylene sulfoneisocyanate with 5 amino-benztriazole. Development was carried out as described in Example 4. The fog value without addition of the stabilizer was 0.113. The fog value was reduced by this stabilizer to 0.06.
- stabilizers according to the invention may be substituted by various groups, for example the following compounds are suitable stabilizers:
- a photographic material which comprises a lightsensitive silver halide emulsion layer and a contiguous auxiliary layer, at least one of which layers contains a derivative of amino-'benztriazole selected from those having the following general formulae:
- R represents a radical selected from the class consisting of alkyl with at least 2 carbon atoms, substituted alkyl with at least 2 carbon atoms, aryl, substi tuted aryl, heterocyclics and substituted heterocyclics;
- a photographic material as defined in claim 1 the silver halide emulsion layer of which contains 4-(3-phen' ylureido) 1,2,3 -b enzotriazole.
Description
arr-mime The invention is concerned with a process for improving the clarity of, photognaphic silver halide emulsions during development at relatively high temperatures. Photognaphiesilver halide emulsions have a tendency at relatively high developer temperatures to give a considerable degree of fogging which appreciably impairs the quality of the picture. Since relatively high developer temperatures frequentlycannot be avoided, because of unfiavorable climatic conditions, it has long been desired to prevent the formation of this development fog by adding suitable substances to thephotographic silver halide emulsion, to the photographic auxiliary layers, or to the processing baths.
A number of substances have also been described which have the effect of keeping the unexposed silver halide clear, but these influence disadvantageously other photographic properties in one way or another. The most important of these substances include benztriazole, which substantially prevents fog formation, but simultaneously shifts the tone of the image undesinably towards blue-black. The use of urea and its substitution products as fog inhibitors is described in U.S. Patent No. 1,763 ,990. However, these tog inhibitors are not able to prevent the development of fog. which occurs at relatively high developer temperatures.
It has now been found that the flog formation at relatively high developer temperatures can largely be prevented if, to the photographic silver halide emulsion or photographic auxiliary layers, such as protective or intermediate layers or the like, are added, prior to the casting, substituted 4(5)-aminobenztriazoles of the following general formula:
in which R represents an aliphatic radical with at least two carbon atoms, an aromatic or heterocyclic radical which in turn may be substituted, and X represents a simple chemical bond, an oxygen atom or an imino radical and in which the benzene nucleus may also carry other substituents.
Suitable substances for this purpose that conform to the foregoing formula are acylated aminobenztriazoles, such as S-benzoylaniinobenztriazole, carbamic acid derivatives such as Scarbethoxyaminobenztriazole, S-carbophenoxyaminobenztriazole, 4-carbophenoxyaminobenztriazole, 4 carbophenoxyam-ino-6eaminobenztriazlole and urea derivatives of benztriazole, such as N-'ethyl-N-(5)- benztriazolyl urea, N-pheny1-N-(4)-benztriazolyl urea, N-phenyl-N-()-benztriazolyl urea, N-(4'-ethoxyphenyl) N-(5)-benztriazolyl urea, N-(3-ch1orphenyl)-N- (5 -benztriazolyl urea, N- 4'-chlorphenyl) N-(5 -benztr-iazolyl urea.
The preparation of these compounds may be 'eifected by known methods.
, The acylated aminobenztriazoles are obtained by reac- Sttes Ptent lice H G CH3 N S H 02 The outstanding efficacy of the substances according to the invention is apparent from the following table, which reproduces the fog values of a silver bromide emulsion according to Bios Final Report No. 252, which emulsion had been cast with and without addition of aminobenztriazole derivatives, after development for 4 minutes at 30 C.
- Fog density after develop- Silver bromide emulsion: ment at 30 C.
Without additive 0.052. With N-ethyl-N-(5)-benztriazo1yl urea (Example 2) 0.031
With N-phenyl-N'-(4) -benztriazolyl urea 0.009 With N-phenyl-N'-(5)-benztriazolyl urea 0.015 With N (4-ethoxyphenyl)-N'-(5 )-benztriazolyl urea 0.015 With N-( 3-chlorphenyl -N-( 5 -benztriazolyl urea 0.017 With N-(4'-chlorpheny-l) -N'-(5 -benztriazolyl urea, 0.009 With S-benzoylaminobenztriazole (Example 1) 0.038 With S-carbophenoxyaminobenztriazole 0.017 With 4carbophenoxyaminobenztriazole 0.033 With 4 carbophenoxyarnino-flaminobenztriazole 0.027 With 4-benzoylaminobenztriazole 0.041 With 5-carboethoxyaminobenztriazole 0.037
1 This compound is also referred to as i ('3-phenyl-ureido)- 1,2,3-henzotriazole. I
If N-phenyl-N'-(5)-benztriaziolyl urea is added to a protective layer, the fog value after development for 4 minutes at 30 C. is 0.045, whereas the fog value without adding the stabilizer increases to 0.195. The emulsion used for this test was the same as mentioned above but this batch was very susceptible to fog formation.
The substances according to the invention may be used in quantities from 5 to 250 mg. per liter of emulsion. 1 liter of emulsion contains approximately 30 g. of silver halide.
'Ihe substances according to the invention are suitable for reducing the fogging of silver chloride, silver bromochloride and silver bromide emulsions, and the maximum eiiect is produced with silver bnomide-ammonia emulsions. The emulsions may contain up to 5 percent silver iodide.
Example 1 A silver bromide emulsion containing g. of AgBr to 3 liters has added thereto 8 cc. per liter of a 1% solution of the compound After adding the other conventional hardening agents, the emulsion is cast on to paper.
The fog value with and without addition of stabilizer, after 4 minutes development at 30 C., are set out in the foregoing table. Development is carried out in a conventional metol-hydroquinone developer which is made alkaline with soda.
Example 2 A silver bromochloride emulsion containing about 35 g. of AgBr and 70 g. of AgCl to three liters has added thereto, 3 cc. per liter of a 1 percent solution of the compound:
and the emulsion is cast after addition of other hardening agents.
When the stabilizer is added the fog value after development for 4 minutes is 0.015 whereas it is 0.124 when no stabilizer has been added.
Example 3 The stabilizer of the formula was prepared as follows:
4 grams of S-aminobenztriazole and 5.2 grams of the hydrochloride of isonicotinic acid chloride are refluxed for 3 hours in 50 cm. of pyridine. The reaction mixture was precipitated by addition of water, filtered and recrystallized from dimethylformamide. The product melts at 3 3 8 C. under decomposition.
50 mg. of the above-mentioned compound were added to 1 liter of a silver bromide emulsion according to Bios Final Report No. 252. The development is achieved in the conventional metal-hydroquinone developer which is made alkaline with soda. After 4 minutes developing at 30 C. the fog value without addition of stabilizer was 0.141 while in the presence of the above-mentioned stabilizer the fog value was only 0.117. The batch of the above-mentioned silver bromide emulsion was very susceptible to fog formation.
Example 4 The stabilizer of the formula velopment was accomplished as described in the foregoing example. After 4 minutes developing at 30 C. the fog value without addition of stabilizer was 0.113 while in the presence of the stabilizer of the above-mentioned formula the fog value was only 0.076.
Example 5 The stabilizer of the formula H o d NH (3 NH 2 I N H2C\ /CH2 s O: H
was prepared by reaction of cyclo-tetra-methylene sulfoneisocyanate with 5 amino-benztriazole. Development was carried out as described in Example 4. The fog value without addition of the stabilizer was 0.113. The fog value was reduced by this stabilizer to 0.06.
It is to be understood that the stabilizers according to the invention may be substituted by various groups, for example the following compounds are suitable stabilizers:
prepared by reaction of butyrolactone with 5-amino-benztriazole;
prepared by reaction of a chloro-substituted fatty acid ester with S-amino-benztriazole;
0 o N mo-ii-oHr-d-NH- prepared by reaction of acetoacetic ester with S-arninobenztriazole;
prepared by reaction of a chloro-substituted alkylene isocyanate with S-amino-benztriazole;
prepared by reaction of alphanaphthyl isocyanate with S-amino-benztriazole.
What is claimed is:
1. A photographic material which comprises a lightsensitive silver halide emulsion layer and a contiguous auxiliary layer, at least one of which layers contains a derivative of amino-'benztriazole selected from those having the following general formulae:
in which R represents a radical selected from the class consisting of alkyl with at least 2 carbon atoms, substituted alkyl with at least 2 carbon atoms, aryl, substi tuted aryl, heterocyclics and substituted heterocyclics; X
6 being a member selected from the group consisting ot a simple chemical bond, an oxygen atom, and an iminc radical, in an amount sufificient to inhibit the formatior of fog in the subsequent development of the silver halide emulsion layer of the said photographic material at 2 relatively high development temperature.
2. A photographic material as defined in claim 1, the light-sensitive silver halide emulsion layer of which con tains an aminobenztriazole derivative as defined it claim 1.
3. The photographic material as defined in claim 1 the contiguous photographic auxiliary layer of which contains the amino-b'enztriazole derivative as defined i1 claim 1.
4. A photographic material as defined in claim 1, the silver halide emulsion layer of which contains 4-(3-phen' ylureido) 1,2,3 -b enzotriazole.
References Cited in the file of this patent FOREIGN PATENTS 350,996 Great Britain June 19, 1931
Claims (1)
1. A PHOTOGRAPHIC MATERIAL WHICH COMPRISES A LIGHTSENSITIVE SILVER HALIDE EMULSION LAYER AND A CONTIGUOUS AUXILIARY LAYER, AT LEAST ONE OF WHICH LAYERS CONTAINS A DERIVATIVE OF AMINO-BENTRIAZOLE SELECTED FROM THOSE HAVING THE FOLLOWING GENERAL FORMULAE:
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA33717A DE1130282B (en) | 1960-01-16 | 1960-01-16 | Process for keeping photographic silver halide emulsions clear at higher developer temperatures |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3082088A true US3082088A (en) | 1963-03-19 |
Family
ID=6928277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US81949A Expired - Lifetime US3082088A (en) | 1960-01-16 | 1961-01-11 | Process for maintaining the clarity of photographic silver halide emulsions at relatively high developer temperatures |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3082088A (en) |
| BE (1) | BE599080A (en) |
| CH (1) | CH393912A (en) |
| DE (1) | DE1130282B (en) |
| GB (1) | GB919061A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0185243A2 (en) | 1984-12-17 | 1986-06-25 | Minnesota Mining And Manufacturing Company | Photosensitive silver halide material for obtaining half-tone black-and-white images and method for half-tone high-contrast reproduction |
| US5192647A (en) * | 1986-10-24 | 1993-03-09 | Fuji Photo Film Co., Ltd. | Method for development processing of silver halide photographic |
| US6376065B1 (en) * | 1998-01-27 | 2002-04-23 | 3M Innovative Properties Company | Fluorochemical benzotriazoles |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5990844A (en) * | 1982-11-16 | 1984-05-25 | Fuji Photo Film Co Ltd | Silver halide photosensitive material |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB350996A (en) * | 1900-01-01 |
-
1960
- 1960-01-16 DE DEA33717A patent/DE1130282B/en active Pending
-
1961
- 1961-01-11 US US81949A patent/US3082088A/en not_active Expired - Lifetime
- 1961-01-13 GB GB1612/61A patent/GB919061A/en not_active Expired
- 1961-01-13 BE BE599080A patent/BE599080A/en unknown
- 1961-01-16 CH CH48161A patent/CH393912A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB350996A (en) * | 1900-01-01 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0185243A2 (en) | 1984-12-17 | 1986-06-25 | Minnesota Mining And Manufacturing Company | Photosensitive silver halide material for obtaining half-tone black-and-white images and method for half-tone high-contrast reproduction |
| US4659647A (en) * | 1984-12-17 | 1987-04-21 | Minnesota Mining And Manufacturing Company | Photosensitive silver halide material for obtaining half-tone black-and-white images and method for half-tone high-contrast reproduction |
| US5192647A (en) * | 1986-10-24 | 1993-03-09 | Fuji Photo Film Co., Ltd. | Method for development processing of silver halide photographic |
| US6376065B1 (en) * | 1998-01-27 | 2002-04-23 | 3M Innovative Properties Company | Fluorochemical benzotriazoles |
Also Published As
| Publication number | Publication date |
|---|---|
| BE599080A (en) | 1961-07-13 |
| GB919061A (en) | 1963-02-20 |
| CH393912A (en) | 1965-06-15 |
| DE1130282B (en) | 1962-05-24 |
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