US3843372A - Gelatino silver halide emulsion layer containing a halogen substituted heterocyclic nitrogen compound,as hardener and a cysteine,methionine or cysteine as latent image regression inhibiting agent - Google Patents
Gelatino silver halide emulsion layer containing a halogen substituted heterocyclic nitrogen compound,as hardener and a cysteine,methionine or cysteine as latent image regression inhibiting agent Download PDFInfo
- Publication number
- US3843372A US3843372A US00346948A US34694873A US3843372A US 3843372 A US3843372 A US 3843372A US 00346948 A US00346948 A US 00346948A US 34694873 A US34694873 A US 34694873A US 3843372 A US3843372 A US 3843372A
- Authority
- US
- United States
- Prior art keywords
- group
- silver halide
- emulsion
- cysteine
- latent image
- 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 abstract description 82
- -1 silver halide Chemical class 0.000 title claims abstract description 60
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 40
- 239000004332 silver Substances 0.000 title claims abstract description 40
- 239000004848 polyfunctional curative Substances 0.000 title claims abstract description 8
- 230000002401 inhibitory effect Effects 0.000 title abstract description 8
- 239000003795 chemical substances by application Substances 0.000 title description 13
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 title description 9
- 229930182817 methionine Natural products 0.000 title description 9
- 235000018417 cysteine Nutrition 0.000 title description 6
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 title description 6
- 229910052736 halogen Inorganic materials 0.000 title description 6
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 title description 5
- 125000005843 halogen group Chemical group 0.000 title description 5
- 229910017464 nitrogen compound Inorganic materials 0.000 title description 5
- 235000006109 methionine Nutrition 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 108010010803 Gelatin Proteins 0.000 claims abstract description 5
- 229920000159 gelatin Polymers 0.000 claims abstract description 5
- 239000008273 gelatin Substances 0.000 claims abstract description 5
- 235000019322 gelatine Nutrition 0.000 claims abstract description 5
- 235000011852 gelatine desserts Nutrition 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 abstract description 10
- 239000000460 chlorine Substances 0.000 abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 abstract description 5
- 239000005864 Sulphur Substances 0.000 abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
- 239000001301 oxygen Substances 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 150000004654 triazenes Chemical class 0.000 abstract description 2
- CVTFNNJUXOBPMI-UHFFFAOYSA-N (1,2-dichloro-2-diphenylphosphanylethyl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(Cl)C(Cl)P(C=1C=CC=CC=1)C1=CC=CC=C1 CVTFNNJUXOBPMI-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- MXOAEAUPQDYUQM-UHFFFAOYSA-N chlorphenesin Chemical group OCC(O)COC1=CC=C(Cl)C=C1 MXOAEAUPQDYUQM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 description 13
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 12
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 10
- 239000012670 alkaline solution Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 238000007792 addition Methods 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 6
- 239000000084 colloidal system Substances 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 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 5
- 229910021612 Silver iodide Inorganic materials 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229960003067 cystine Drugs 0.000 description 5
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 5
- 229940045105 silver iodide Drugs 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229960002433 cysteine Drugs 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- JKAPWXKZLYJQJJ-UHFFFAOYSA-N 2,4-dichloro-6-methoxy-1,3,5-triazine Chemical compound COC1=NC(Cl)=NC(Cl)=N1 JKAPWXKZLYJQJJ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004133 Sodium thiosulphate Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 description 1
- PTRQEEVKHMDMCF-ROUUACIJSA-N (2r)-3-[[(2r)-2-carboxy-2-(phenylmethoxycarbonylamino)ethyl]disulfanyl]-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound N([C@@H](CSSC[C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C(O)=O)C(=O)OCC1=CC=CC=C1 PTRQEEVKHMDMCF-ROUUACIJSA-N 0.000 description 1
- JDBGDMZILOWAHV-UHFFFAOYSA-N 4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NC1=NC(Cl)=NC(Cl)=N1 JDBGDMZILOWAHV-UHFFFAOYSA-N 0.000 description 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- 150000000644 6-membered heterocyclic compounds Chemical class 0.000 description 1
- 241001522296 Erithacus rubecula Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229960001305 cysteine hydrochloride Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- NXPHCVPFHOVZBC-UHFFFAOYSA-N hydroxylamine;sulfuric acid Chemical compound ON.OS(O)(=O)=O NXPHCVPFHOVZBC-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960004452 methionine Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- G03C1/30—Hardeners
-
- 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
- Photographic silver halide materials usually comprise a colloid binder for the silver halide and the most common of these colloid binders is gelatin. It is usual to add a hardening agent for the colloid to the aqueous silver halide emulsion coating mixture when emulsion is coated onto the base support. A great amount of time has been expended in searching for suitable colloid hardeners and a number of very useful compounds and classes of compounds have been discovered. However each of these hardeners and classes of hardeners suffer from certain inherent defects but nevertheless these compounds are used because it has been impossible to discover a hardening agent which has no deleterious side effects.
- One class of hardening agents which are commonly used are halogen substituted 6-membered heterocyclic rings which comprise, two or three nitrogen atoms in the ring system. Examples of such hardening agents are compounds of the formula I to III:
- X is a chlorine or bromine atom and R is a substituent group for example a methoxy group (preferably dichloro substituted triazines).
- the effect of such compounds is often increased by adding a base to the heterocyclic nitrogen compounds in the hardening mixture.
- a base for example 1,4-diaza-dicyclo-(2, 2,2)-octane (Dabco) is often used with the triazine of the above formula I, in order to increase its hardening action.
- Latent image regression manifests itself as an apparent decrease in the sensitivity of exposed material. Usually the longer the period over which exposed material is kept before development the greater the apparent decrease in sensitivity of the material. This apparent decrease in sensitivity is enhanced by storing the material at elevated temperatures. With colour photographic material containing several emulsion layers the consequences of latent image regression are more serious because they are more obvious since it generally arises that the regression is not uniform for the several emulsion layers and there is consequently a shift in the colour balance as well as an apparent loss of sensitivity. Nevertheless because of the very desirable hardening actions obtained with the above defined heterocyclic nitrogen compounds it is often required to use these hardening agents in spite of their inherent tendency to produce latent image regression in photographic materials.
- the colloid binder of a silver halide emulsion layer of the material is hardened by means of a hardening agent which is a halogen substituted 6-membered heterocyclic ring which comprises two or three ring nitrogen atoms
- a hardening agent which is a halogen substituted 6-membered heterocyclic ring which comprises two or three ring nitrogen atoms
- the step of adding to the silver halide emulsion an aqueous solution of a compound which, in its free amino acid state if it is an amino acid, corresponds to one of the formulae wherein R and -R',, independently from one another, represent a hydrogen atom, an alkyl group, a substituted alkyl group, an aralkyl group, a substituted aralkyl group, an allyl group, an alkyl-oxy-carbonyl group, an aralkyloxy-carbonyl group or an acyl group of the formula R -CO-- where R is an al
- the compounds of formulae (1) and (2) wherein p and/or q are 2 contain at least one amino group and at least one carboxylic acid group.
- Such amphoteric compounds are capable of forming salts with strong acids and with bases such as alkali metals. Therefore the compounds may be used for the present process in the form of salts, provided the salts are soluble in water.
- An example of a substituted alkyl group i hydroxymethyl.
- An example of a substituted alkyl group in the R position is trifluormethyl.
- An example of a substituted aralkyl group is hydroxymethyl benzyl.
- An example of a substituted aryl group is parachlorophenyl.
- the compounds in their free amino acid state correspond to the formula wherein R represents the radical Q-om-o-o cor preferably a hydrogen atom.
- Some of the compounds of formula (1) are advantageously added to the silver halide emulsion as a dilute aqueous alkaline solution.
- An example of such a compound is cystine. Cysteine or methionine are with advantage added as an aqueous solution of the hydrohalide or as an aqueous alkaline solution.
- the preferred amount of the compound of formula (1) or (2) to be added to the silver halide emulsion is from 0.01 to 2.5 millimoles per mole of silver halide present in the emulsion.
- the quantities of these compounds to be present is very small but they are very efiicacious in preventing latent image regression as illustrated in the Examples which follow.
- Example 1 A fast iodobromide emulsion was prepared, in gelatin solution, having 3.2 mole percent of silver iodide. This emulsion was digested at an elevated temperature to maximum sensitivity in the presence of sodium thiosulphate and a gold salt. The emulsion was then stabilised by the addition of a tetraazaindene compound and cooled. A wetting agent was then added to the emulsion which was reheated, brought to a pH of 6 and divided into portions. One portion was coated onto film strips without any further additions being made to it. This was the control emulsion.
- each test one strip of the control emulsion and the strips of the test emulsions were all exposed through a step-wedge and then incubated for 7 days at 60% RH. at 42 C. such conditions being chosen to accelerate latent image regression.
- the figures set out show the difference in speeds between the sets of strips exposed, stored 7 days, and then processed compared with the set of strips exposed just prior to processing.
- the greatest latent image regression is shown in the emulsion which contained the triazine+Dabco hardener combination but no N N-dicarbobenzoxy-l-cystine.
- the N,N-dicarbobenzoxy-l-cystine-l-cystine was also present, the latent image regression was considerably reduced.
- Example 3 A medium speed iodo-bromide emulsion containing 6.4 mole percent of silver iodide was prepared and digested in a manner similar to that of Example 1. To this emulsion was then added wetting agents and an alkaline solution of the colour former 3-p-methoxybenzoylacetylamino 4 (N-methyl-N-octadecylamino) benzoic acid (105 g. per 1 /2 moles of silver halide). The pH was adjusted to 9.7 and the emulsions divided into portions. One portion was coated onto film strips without further addition. This was the control emulsion.
- 3-p-methoxybenzoylacetylamino 4 N-methyl-N-octadecylamino
- X represents a chlorine or bromine atom and a latent image regression inhibiting compound of the formula wherein R and R' independently from one another, represent a hydrogen atom, an alkyl group, a hydroxymethyl group, an aralkyl, a hydroxymethyl benzyl group, an allyl group, an alkyl-oxy-carbonyl group, an aralkyloxy-carbonyl group or an acyl group of the formula R CO where R is an alkyl or trifluoromethyl group, an aralkyl or hydroxymethyl benzyl group or an aryl or p-chlorophenyl group, B and B represent an oxygen or sulphur atom and p, q and k each is 1 or 2, or a watersoluble salt of a sulphur compound of formula (1) or (2) the sulphur compound being present in an amount ranging from 0.01 to 2.5 millimoles per mole of silver hal
- a silver halide emulsion layer according to claim 1 which comprises as the latent image regression inhibiting compound:
- R represents a hydrogen atom or the radical or a water-soluble salt thereof.
- a silver halide emulsion layer according to claim 1 which comprises as the latent image regression inhibiting compound:
- a silver halide emulsion layer according to claim 1 which comprises as the latent image regression inhibiting compound:
- a silver halide emulsion layer according to claim 1 which comprises as the latent image regression inhibiting compound:
- a silver halide emulsion layer according to claim 1 which comprises as the latent image regression inhibiting compound:
- a silver halide emulsion layer according to claim 1 which comprises employing as the hardening agent 4-(2,4- dichloro-1,3,5-triazinylamino)-benzene sulphonic acid or 2,4dichloro-6-methoxy-1,3,5-triazine.
- a silver halide emulsion layer according to claim 1 which comprises employing the hardening agent together with 1,4-diaza-dicyclo-(2,2,2)-octane.
Landscapes
- 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)
- Photosensitive Polymer And Photoresist Processing (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1561572A GB1394372A (en) | 1972-04-05 | 1972-04-05 | Photographic emulsions |
| GB1561672A GB1390237A (en) | 1972-04-05 | 1972-04-05 | Photographic emulsions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3843372A true US3843372A (en) | 1974-10-22 |
Family
ID=26251432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00346948A Expired - Lifetime US3843372A (en) | 1972-04-05 | 1973-03-29 | Gelatino silver halide emulsion layer containing a halogen substituted heterocyclic nitrogen compound,as hardener and a cysteine,methionine or cysteine as latent image regression inhibiting agent |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3843372A (zh) |
| JP (1) | JPS4917720A (zh) |
| CH (1) | CH569305A5 (zh) |
| FR (1) | FR2179136B1 (zh) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4057429A (en) * | 1975-04-09 | 1977-11-08 | Agfa-Gevaert, N. V. | Preparation of photographic silver halide emulsions |
| 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 |
| US4281059A (en) * | 1978-12-12 | 1981-07-28 | Konishiroku Photo Industry Co., Ltd. | Photographic material |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2438716A (en) * | 1944-10-06 | 1948-03-30 | Gen Aniline & Film Corp | Stabilized silver halide emulsions |
| BE594454A (zh) * | 1959-09-04 |
-
1973
- 1973-03-22 CH CH416873A patent/CH569305A5/xx not_active IP Right Cessation
- 1973-03-29 US US00346948A patent/US3843372A/en not_active Expired - Lifetime
- 1973-04-04 FR FR7312202A patent/FR2179136B1/fr not_active Expired
- 1973-04-05 JP JP48038348A patent/JPS4917720A/ja active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4057429A (en) * | 1975-04-09 | 1977-11-08 | Agfa-Gevaert, N. V. | Preparation of photographic silver halide emulsions |
| US4230796A (en) * | 1978-01-18 | 1980-10-28 | E. I. Du Pont De Nemours And Company | High speed lithographic film element |
| US4281059A (en) * | 1978-12-12 | 1981-07-28 | Konishiroku Photo Industry Co., Ltd. | Photographic material |
| 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 |
|---|---|
| JPS4917720A (zh) | 1974-02-16 |
| FR2179136B1 (zh) | 1977-02-04 |
| CH569305A5 (zh) | 1975-11-14 |
| FR2179136A1 (zh) | 1973-11-16 |
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| JPS63172265A (ja) | ハロゲン化銀写真乳剤 | |
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