US1763989A - Photoctbaphic light-sensitive matebiax and pbocesb pob itakxng pat - Google Patents
Photoctbaphic light-sensitive matebiax and pbocesb pob itakxng pat Download PDFInfo
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- US1763989A US1763989A US1763989DA US1763989A US 1763989 A US1763989 A US 1763989A US 1763989D A US1763989D A US 1763989DA US 1763989 A US1763989 A US 1763989A
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- United States
- Prior art keywords
- light
- compound
- sensitive
- emulsion
- photoctbaphic
- Prior art date
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- 150000001875 compounds Chemical class 0.000 description 60
- 239000000839 emulsion Substances 0.000 description 58
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 50
- 229910052757 nitrogen Inorganic materials 0.000 description 32
- 239000000084 colloidal system Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 230000000087 stabilizing Effects 0.000 description 18
- 229920000159 gelatin Polymers 0.000 description 16
- 235000019322 gelatine Nutrition 0.000 description 16
- 239000000463 material Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 108010010803 Gelatin Proteins 0.000 description 12
- 239000008273 gelatin Substances 0.000 description 12
- 235000011852 gelatine desserts Nutrition 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 229910052709 silver Inorganic materials 0.000 description 12
- 239000004332 silver Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000003213 activating Effects 0.000 description 10
- 230000002401 inhibitory effect Effects 0.000 description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 150000003378 silver Chemical class 0.000 description 8
- -1 silver halides Chemical class 0.000 description 8
- GGCZERPQGJTIQP-UHFFFAOYSA-M Sodium 2-anthraquinonesulfonate Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-M 0.000 description 6
- 230000000875 corresponding Effects 0.000 description 6
- 150000003949 imides Chemical class 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 230000001235 sensitizing Effects 0.000 description 6
- 231100000202 sensitizing Toxicity 0.000 description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 6
- 239000001828 Gelatine Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 230000000630 rising Effects 0.000 description 4
- 231100000489 sensitizer Toxicity 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1,2,3-triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 102000009027 Albumins Human genes 0.000 description 2
- 108010088751 Albumins Proteins 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 240000006600 Humulus lupulus Species 0.000 description 2
- 235000008694 Humulus lupulus Nutrition 0.000 description 2
- 101710044258 MARCHF2 Proteins 0.000 description 2
- 206010034960 Photophobia Diseases 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N Phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N Saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 229940081974 Saccharin Drugs 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M Silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- XUARKZBEFFVFRG-UHFFFAOYSA-N Silver sulfide Chemical compound [S-2].[Ag+].[Ag+] XUARKZBEFFVFRG-UHFFFAOYSA-N 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N Succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 238000009666 routine test Methods 0.000 description 2
- 235000019204 saccharin Nutrition 0.000 description 2
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
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 colloidal material used contains minute quantities of biochemical ori that have a sulfiding or sulfiding Y and re ucing' action on the silver halides. These materials havevbeen described in the United States Patent,1No. 1,600,736, Punnett, September 21, 1926, and a process istherein given for separating these bodies from the colloidal materiaL' Compounds arelikewise added to photographicfiemulsions to extend the spectrum. 1
- gelatino silver halide developing-out emulsions it is generally advantageous to add from .01 to 10 gramsof therestraining substance per 1,000 grams of, gelatine. 'Where gelatine is used in more than one operation,
- these fgelatins may be differentially treated with the restrainin bodies as will be understood by those skille in the art; 7 5o
- Our present fog-inhibiting compounds are I effective in all kinds of emulsions ordin in the colloids for the emulsions in the same way asth ose-set forth in UnitcdStates Pat-v exit-No. 1,574,944, March2, 1926.
- pane meaeae emulsion in gelatin may prepared as set forth in said-patent,.page 3; After the emulsion is prepared, it may be melted and the 1 roper amount of stabilizing compound thoroughly mixed into it. This mixing is convemently efiectedby dissolving the sta-.-
- tographic emulsion and known equiv ents may be used therefor without in any way departing'from our invention or sacrificing any of the advantages derived therefrom;
- saidcompound bemg of the type in which R 'nitrogen free organic radical and X and are'selected from activatin being solu le ina water miscible solvent.
- v and and Y are selected fromthe group comprising the activating electin -negative electro-negjative radicals,v said compoun in which R is anitrogen free organic radical radicals containing sulfur, carbon, and imide nitrogen.
- I colloid, precede 'depends said compound being ofthe type RY NH in which R is a nitrogen free organic radical and X and Y are selected from the group comprising the activating electro negative radicals containing sulfur, carbon, and imide nitrogen, said compound being soluble in a water miyible solvent.
- a photographic emulsion comprising a colloid, particles of photographic silver salts suspended therein, and an added compound therein which stabilizes the emulsion and on which at least part of the light sensitiveness depends, said compound being of the type R-Y in which R is a nitrogen free organic radical and X and Y are selected from the group of carbonyl, sulfuryl and imid nitrogen, sald compound being soluble in a water misc ble solvent.
- a photographic emulsion comprising a colloid, particles of photographic silver salts suspended therein, and anadded compound therein which stabilizes the emulsion andon which at least part of the light sensitiveness depends, said compound being of the type R-Y in which R is a-nitrogen free organic radical and X and Y' compriseactivatin electronegative radicals, sald compound orminga closed ring and soluble in a water miscible solvent V l 7, In the process of preparing a develop-.
- ing-out colloid sensitive silver salt emulsion 1 stabilizing the light sensitiveness thereofby" incorporating a stabilizing compound therein' in an amount corresponding to .001 to 1% by weight, of the gelatin present, said compound being of the type in which Risa nitrogen free organic radical and X and Y comprise activating electro negative radicals.
- veloping-out ⁇ colloi'd sensitive silver salt emulsign stabilizing the light sensitiveness thereof by incorporating a stabilizing compound thereinin an amount corresponding to .001 to 1% by weight, of the gelatin ,eso -3 present, said compound being of the type NH R-Y in which R is a nitrogen free organic radical and X and Y com rise activating electro-- negative radicals, said compound being soluble in a water miscible solvent.
Description
Patented June '17, 1930 I sAMUEL E. snmrnnn AND EUGENE r. ren-rm,
smnonsmo Eurmnxonn: 'rrorz 'OI'INEW Yonxcountr or aocnnsrnn,
or nocnEsrEa, YORK, ns-
nnw roar, A coarom- ,rno"roenarnic imm m mmm m rnoc ssr-on 111mm no Drawing. Application filed February This invention relates to photographic light-sensitivematerials. and to processes of making such materials.
In the manufacture of photographic emul- 3 sions it is known that the colloidal material used contains minute quantities of biochemical ori that have a sulfiding or sulfiding Y and re ucing' action on the silver halides. These materials havevbeen described in the United States Patent,1No. 1,600,736, Punnett, September 21, 1926, and a process istherein given for separating these bodies from the colloidal materiaL' Compounds arelikewise added to photographicfiemulsions to extend the spectrum. 1
' Photographic emulsions, if prepared with added, and often when they contaln only the native sensitizing bodies, have a tendency to fog the light-sensitive materials contained therein. The more powerful the sensitizer, the greater is the tendency to fog. -While such f0 ging action is associated with the \speed 0 the inception of: the latent image, 26 nevertheless, apparent fog must be avoided with its attendant loss in the commercial value of the product.
The object of the present invention is to provide a series of compounds for the purpose of stabilizing light-sensitive materials and thereby correcting the hereinabovedescribed tendencies without markedly retard= 1n rifls} Other objects will hereinafter appear;
We have now found a class of anti-sensitizing or fog-inhibiting compounds which are effective in the production of light sensitive emulsions and in the reparation of col- I loidal intermediates Ifort e manufacture of 40 such emulsions. This new class of substances may be indicated :by the following formula:
' (:CR),or imidnitrogen (:NR).
15 the light-sensitivity far into the red end of the sensitivity of the light-sensitivemate- The photographic sensitivity of silver hal- I thioanalides a class of bodiesof the general formula:
f sensitivity I restraint and fog inhibition is not essential-t0 the ,practical application of ourydiscovery, it exhibits the reasoning by which we were led to it.
Proceeding from these conceptions, we have sought for substances which could com-' bine with the silver halide and particularly at-the boundary of a. growing silver sulphide or other sensitizing speck.
Forexamyop if X and are substituted by H; groupin'gs, there results a compound which is only weakly active in its fog inhibiting or sta 'bi lizing action. .Thesubstitution'of oxygen for H attached to one of the carbon atoms, or, in other words, the substitution of 00 for X and CH tor Y, somewhat increases the eii'ectiveness 'ofthe substance. A more powerful body results when the carbonyl v group issubstitutedafoi" both X and Y. "An
-example,of this type of substance is diacet 1e, in the structure iven above amide, phthalimide, the pyrrol and pyrrol j derivatives suchas succinimide. A: powerv ful to inhibitor or stabilizer is also obtained if car onyl be substituted fornX and a sulfuryl be substituted for Y. In this. case we have'sulfo-ainides and their derivatives, such .for'example as saccharin. I
'There,areother'configurations of the mud group which are also active in respect ottlns inhibitoryaotion on the. fogging of s lver halides. :Itimid' nitrogen replaces the X while .CH,. 'imid-nitrogen, or carbonyl, 'relaces the Y in our above configuration, we have aserie's of compounds which show this activit -The t e pyraz odone ring, an the osotriazo e ring arefexamples of this class'of substances. 1 fIn orde'r'to .thoroughlyand uniformly in- 5 corporate the v non-fogging agent into the I :emulsion'it is usually necessary to dissolve the .material' in asuit'able' solvent such as water or alcohol, or acetone. .Other solvents y or mixturesofthem, of course, may be used 20 that are com atible with the emulsion but we have-found e: above-solvents to be most desirable: I I Theproportionsinwhichthesecompounds are incor orated'in the emulsions, or in the co1loids ibrflthe,v emulsions, are important.
pyrazolone rin pyrazole 6 Too much-of them will often desensltize the emulsion. :Th'e' mairimum proportions which can be used practically vary slightliwith the particularsensitizing compound w ich is selected, with the ratio 'ofgelatin to silver halide in the emulsion, with the t pe of emulsion as regards grain sizean alkalinity, with, the amount of natural sensitizer' also present. in the latin when the latter is man- 'ufactured, wit the particular silver or halides employed, or with the fog standards which are set bythe emulsion manufacture. The optimum proportion is readily obtained by routine test. s
With gelatino silver halide developing-out emulsions, it is generally advantageous to add from .01 to 10 gramsof therestraining substance per 1,000 grams of, gelatine. 'Where gelatine is used in more than one operation,
. as for example in small amounts for precipitation, or in larger amounts at later melt- -ings, these fgelatins -may be differentially treated with the restrainin bodies as will be understood by those skille in the art; 7 5o Our present fog-inhibiting compounds are I effective in all kinds of emulsions ordin in the colloids for the emulsions in the same way asth ose-set forth in UnitcdStates Pat-v exit-No. 1,574,944, March2, 1926. For example, a; mixedjsilver bromide and iodide ly. met with, such as orthochromatic, pane meaeae emulsion in gelatin may prepared as set forth in said-patent,.page 3; After the emulsion is prepared, it may be melted and the 1 roper amount of stabilizing compound thoroughly mixed into it. This mixing is convemently efiectedby dissolving the sta-.-
bilizin substance in a suitable solvent or mixture 0 them, and then stirring such solution into the emulsionu Q 7 7 While our novel sensitizing compounds are preferably used with gelatin, they, never-.
'theless,'have utility with emulsions made in other colloids or agar 1! 'ar, albumins, gums like gum arabic and ce ulose derivatives. Our compounds likewise have utility in emulsions in which different kinds .of silver salts are present suchas silver bromide. I
, tographic emulsion and known equiv ents may be used therefor without in any way departing'from our invention or sacrificing any of the advantages derived therefrom;
Having thus described our invention, what 1 we claim as new and desire to secure by Letters Patent is:
1. A photographic emulsion com rising a colloid, particles of photogra hie a ver salts suspended therein, and an a dad compound in which R is a nitrogen free organic radical and X and Y are selected from activating electro-negative radicals. v
2. A photographic emulsion com rising a colloid, partic es of photogra hic silver salts suspendedtherein, and an a ded compound therein which stabilizes the emulsion and-.on"
, which at least part of the li ht sensitiveness depends, saidcompound bemg of the type in which R 'nitrogen free organic radical and X and are'selected from activatin being solu le ina water miscible solvent.
v and and Y are selected fromthe group comprising the activating electin -negative electro-negjative radicals,v said compoun in which R is anitrogen free organic radical radicals containing sulfur, carbon, and imide nitrogen.
I colloid, partie 'depends, said compound being ofthe type RY NH in which R is a nitrogen free organic radical and X and Y are selected from the group comprising the activating electro negative radicals containing sulfur, carbon, and imide nitrogen, said compound being soluble in a water miyible solvent.
5. A photographic emulsion comprising a colloid, particles of photographic silver salts suspended therein, and an added compound therein which stabilizes the emulsion and on which at least part of the light sensitiveness depends, said compound being of the type R-Y in which R is a nitrogen free organic radical and X and Y are selected from the group of carbonyl, sulfuryl and imid nitrogen, sald compound being soluble in a water misc ble solvent.
6. A photographic emulsion comprising a colloid, particles of photographic silver salts suspended therein, and anadded compound therein which stabilizes the emulsion andon which at least part of the light sensitiveness depends, said compound being of the type R-Y in which R is a-nitrogen free organic radical and X and Y' compriseactivatin electronegative radicals, sald compound orminga closed ring and soluble in a water miscible solvent V l 7, In the process of preparing a develop-. ing-out colloid sensitive silver salt emulsion, 1 stabilizing the light sensitiveness thereofby" incorporating a stabilizing compound therein' in an amount corresponding to .001 to 1% by weight, of the gelatin present, said compound being of the type in which Risa nitrogen free organic radical and X and Y comprise activating electro negative radicals.
8. In 'the process of preparing a. de-
veloping-out \colloi'd sensitive silver salt emulsign, stabilizing the light sensitiveness thereof by incorporating a stabilizing compound thereinin an amount corresponding to .001 to 1% by weight, of the gelatin ,eso -3 present, said compound being of the type NH R-Y in which R is a nitrogen free organic radical and X and Y com rise activating electro-- negative radicals, said compound being soluble in a water miscible solvent.
9. In the process of preparing a develop ng-out colloid sensltive silver salt emulsion, stabilizing the light sensitiveness thereof by incorporating a stabilizing compound therein in an amount corresponding to .001 to 1% by weight, of the gelatin present, said compound being of the type Nn R-Y in which R is a nitrogen free organic radical and X and Y are selected from the group of electro-negative radicals comprising carbonyl, sulfuryl and imide nitrogen.
10. The process of making an inter-. mediate for use in the preparation of photographic emulsions which comprises incorporating in the gelatin .001 to 1% by weight thereof of a stabilizing come pound, said compound being of the type in which Risa nitrogen free organic radical r compound being selected from the group of heterocyclic compounds containing nitrogen in the r1ng and consisting of those compounds containing a -pyrazolone ring,'a pyrazole ring, a pyrazolo'done'ring or an osotriazole.
rmsg. k igned at Rochester, New York this 19th day of February, 1929. SAMUEL E. SHEPPARD. EUGENE P. WIGHTMAN.
Publications (1)
Publication Number | Publication Date |
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US1763989A true US1763989A (en) | 1930-06-17 |
Family
ID=3420069
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Application Number | Title | Priority Date | Filing Date |
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US1763989D Expired - Lifetime US1763989A (en) | Photoctbaphic light-sensitive matebiax and pbocesb pob itakxng pat |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2588538A (en) * | 1948-08-06 | 1952-03-11 | Ilford Ltd | Stabilizers in photographic emulsions and developers |
US2668113A (en) * | 1951-01-26 | 1954-02-02 | Du Pont | Photographic antibronzing agents |
US2710256A (en) * | 1951-04-25 | 1955-06-07 | Gen Aniline & Film Corp | Photographic print-out process |
US3106467A (en) * | 1960-10-19 | 1963-10-08 | Eastman Kodak Co | Bis-pyrazoles as antifoggants for photographic silver halide emulsions |
US4349623A (en) * | 1979-06-15 | 1982-09-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic materials |
-
0
- US US1763989D patent/US1763989A/en not_active Expired - Lifetime
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2588538A (en) * | 1948-08-06 | 1952-03-11 | Ilford Ltd | Stabilizers in photographic emulsions and developers |
US2668113A (en) * | 1951-01-26 | 1954-02-02 | Du Pont | Photographic antibronzing agents |
US2710256A (en) * | 1951-04-25 | 1955-06-07 | Gen Aniline & Film Corp | Photographic print-out process |
US3106467A (en) * | 1960-10-19 | 1963-10-08 | Eastman Kodak Co | Bis-pyrazoles as antifoggants for photographic silver halide emulsions |
US4349623A (en) * | 1979-06-15 | 1982-09-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic materials |
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