US2732303A - Antifoggevg and hardening agents for - Google Patents
Antifoggevg and hardening agents for Download PDFInfo
- Publication number
- US2732303A US2732303A US2732303DA US2732303A US 2732303 A US2732303 A US 2732303A US 2732303D A US2732303D A US 2732303DA US 2732303 A US2732303 A US 2732303A
- Authority
- US
- United States
- Prior art keywords
- photographic
- emulsions
- silver halide
- fog
- compounds
- 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 claims description 51
- 150000001875 compounds Chemical group 0.000 claims description 28
- -1 SILVER HALIDE Chemical class 0.000 claims description 20
- 229910052709 silver Inorganic materials 0.000 claims description 20
- 239000004332 silver Substances 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000011534 incubation Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007767 bonding agent Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- NJXWZWXCHBNOOG-UHFFFAOYSA-N 3,3-diphenylpropyl(1-phenylethyl)azanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(C)[NH2+]CCC(C=1C=CC=CC=1)C1=CC=CC=C1 NJXWZWXCHBNOOG-UHFFFAOYSA-N 0.000 description 1
- BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- OTBGYEMEWAHAFW-UHFFFAOYSA-N Cl[Br]I Chemical compound Cl[Br]I OTBGYEMEWAHAFW-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
- 101100168115 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) con-6 gene Proteins 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- UDGLEEJNZQQJOJ-UHFFFAOYSA-N benzene-1,4-diol [4-(methylamino)phenyl] hydrogen sulfate Chemical compound S(=O)(=O)(O)OC1=CC=C(C=C1)NC.C1(O)=CC=C(O)C=C1 UDGLEEJNZQQJOJ-UHFFFAOYSA-N 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000013101 initial test Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 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 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 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
- G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
- G03C1/043—Polyalkylene oxides; Polyalkylene sulfides; Polyalkylene selenides; Polyalkylene tellurides
Definitions
- This invention relates to compounds useful as foginhibiting agents or hardening agents for photographic emulsions, and to photographic emulsions containing them.
- an object of our invention to provide a method for stabilizing photographic emulsions.
- Another object of our-invention is to maintain the sensitivity and fogof silver halide emulsions at or close to initial optimum values under keeping conditions of high temperature and humidity.
- a further object is to provide photographic silver halide emulsions containing antifoggants (or stabilizers) or hardening agents.
- the compounds selected from those represented by Formulas 1 and 2 above are, in general, known compounds.
- the compounds represented by Formula 1 above can advantageously be prepared by reacting a halogenated aliphatic carboxylic acid together with ethylene oxide in vary, in ⁇ ; amounts.
- ethylene oxide By varying the quantity of ethylene oxide, it is possible to produce monoesters wherein n has any desirable value. Accordingly, n can represent any positive integer, e. g., 1 to 200, or more.
- This method of making monoesters is well known and has been previously described in the prior art.
- the reaction is carried out in the presence of an acidic catalyst, such as boron trifluoride (generally in the form of a complex, such as with acetic acid, diethyl ether, etc.).
- the compounds embraced by Formula 2 above can advantageously be prepared by reacting together an acid halide (e; g. chloride, etc.) of a halogenated aliphatic carboxylic acid with asuitable glycol, such as ethylene glycol, diethylene glycol, triethylene glycol, the polyethylene glycols, etc.
- a suitable glycol such as ethylene glycol, diethylene glycol, triethylene glycol, the polyethylene glycols, etc.
- n can also represent any positive integer, e. g. l to 200 or more.
- the condensations can advantageously be carried out in the presence of an acid-bonding agent, such as pyridine, quinolinefetc although such acid-bonding agents need not be employed unless so desired.
- an inert solvent such as dioxane, diethyl ether, etc., can be employed.
- R represents a halogenoalkyl group
- the compounds of Formula 2- can be prepared by heating together, in the presence of an acid esterification catalyst, a glycol, such as those listed above, with a halogenated aliphatic carboxylic acid.
- Suitable esterification catalysts comprises sulphuric acid, p-toluenesul.- phonic acid, etc.
- the speed of the esterification can be increased through the use of water-entraining agent, such as benzene, toluene, etc., which can be azeotropically distilled ofi.
- a mixture of esters When employing higher molecular weight glycols in the methods outlined above, a mixture of esters generally results. For example, when a large amount of ethylene oxideis employed with respect to the quantity of halogenated aliphatic carboxylic acid, the reaction mixture contains a mixture of esters wherein the value of n in Formula 1 varies. Likewise, when a polyglycol is reacted with a halogenated aliphatic carboxylic acid or carboxylic halide, a mixture of diesters wherein the value of n,varies, results. While it is sometimespossible to separatethese mixtures into the -cpmponent esters,- i t is not necessary, to do so. Accordingly, in the table given-below, in some cases only the average value of n is set forth. Mixtures of esters, or pure esters, can be'employed to advantage in practicing our invention. Mixtures of monoesters with diesters are also effective.
- Triethylene glycol (30 gms. 0.2 mol.) was cooled to 0 C. in an ice-bath and redistilled chloracetyl chloride (54 gms. 0.48 mol.) added slowly with stirring. The temperature was kept below 20 C. during the addition, which was complete in about 20 inins. The solution was stirred for a further 30 minutes and the excess acid chloride removed by heating on the steam-bathat waterpump pressure. The viscous oil "ensued? 'B.-'-P. 22 8 230 C. /20 m m., yield 55 gms.. (91% theoretical).
- Example 2 Trie thyleneglycol-bis (p-chloropropionate) GhIOracetic acid (-19 gins. 0.2 inol.) was dissolved in sea: he (100 1111.) and boront'rifiuorideadd'e'd asth'e ether complex (-1 cc). Pure ethylene okide was passed into tlie-solnfidn ats 'e'h a 'ra't'ethat the temperature 'did not exee d 40 C. The new "of ethylene oxide was stopped "when an increase irrweight of 26 gms. was observed his.
- the fog inhibitors which we propose to use areadded to the emulsion during the process of manufacture, to avoidlossof sensitivity 'andto inhibit the growth of fog with passage of time under'nonideal conditions of "storage.
- a solution of the "compounds of the invention when added in suitable concentration, before coating, to ims ensi tize d, chemically “sensitized, or optically sensitized photographic emulsions does not appreciably affect the 'sensitome'tric values for sensi'tivity'and fog when measuremerits are "madesoon after coating.
- sensit om etric "measurements are made at "appreciable intervals 'of time
- the emulsions can b e unse nsitiz ed, or sensitized 'withch'emical sensitizers or -optical "sensitizeg l sulfur-sanitizers such as mose'ana sea in Sheppard U. S.;Patent 1,74,9 t4ean advantageously b eadded to t'he'iemulsioris in the"c61'1v'entional nia nner. "Alsofvarioiis"gold sfisitizers canbeem- '4 ployed in the photographic emulsions stabilized according to our invention.
- the antifoggant or stabilizing activity of a number of compounds coming within the scope of general Formulas l and 2 was determined by incubation of a photographic emulsion at a temperature of 120 F. for three days at a relative humidity of 94% as shown in the table below.
- the efliciency of the various antifoggants was then evaluated by measuring the speed and fog of the incubated emulsions containing an antifoggant and comparing these measurements with those of the same batch of emulsion before incubation. Also, similar measurements were made on aphotographic emulsion containing no antifoggant, both before and after incubation. The tests were made using a high speed silver bromiodide emulsion exposed on an Eastman type Ib 'sen'sitor'neter with an exposure of second and then developed for five minutes in a developer of the following composition:
- D .Tnethyleneglycol-mono (chloracetate)
- E Ethyleneglycol-bls (chloracetnte)
- F Tr1ethyleneglyc0l-bis (trichloracetate) .
- G Triethylencglycol-rnono (bromacetate).
- H Polyethyleneglycol-mono (bromacetate) (71 avg. 60).
- J Polyethyleneglycol-mono (lodoaeetate) (n avg. 50).
- Suitable dispersing agents for the silver halide emulsions'stabilized according "to our invention comprisegelatin, -or other colloids, -such as collodion, albumen, cellulose organic “derivatives, synthetic resins, etc.
- the optimum amount of fog-inhibitingagent can be determined by making the customary tests employed-in emulsion making.
- the optimum amount for a given emulsion will vary depending on the presence-of emulsion addenda, such as chemical sensitizers, optical sensitizers, etc. In general, we have found that from I 1.0. g. to 15 .O g. of fog inhibiting agent per mole of silver halide is sufficientfor the purpose of our' invention.
- certain of the antifogging compounds employed in our invention also have the property of hardening photographic emulsions.
- This effect for a number of compounds is summarized in the following table wherein the softening temperature of the emulsion containing no antifoggant is compared with a similar batch of emulsion containing an antifoggant, the determinations being made before incubation, after three days incubation at 120 F. and a relative humidity of 94%, and after seven days incubation at 120 F. and a relative humidity of 42%.
- the results are summarized in the following table.
- K Polyethyleneglycol-bis (chloracetate) (n avg.
- R represents a halogenated alkyl group containing from 1 to 2 carbon atoms and n represents a positive integer.
- R represents a halogenated alkyl group containing from 1 to 2 carbon atoms and n represents a positive integer of from 1 to 200.
- R represents a halogenated alkyl group containing from 1 to 2 carbon atoms
- n represents a positive integer of from 1 to 200.
- R represents a halogenated alkyl group containing from 1 to 2 carbon atoms and n represents a a positive integer of from 1 to 200.
- R represents a chlorinated alkyl group containing from 1 to 2 carbon atoms and n represents a positive integer of from 1 to 200.
- R represents a halogenated alkyl group containing from 1 to 2 carbon atoms and n represents a positive integerof from 1 to 200.
- n has an average value of 9.
- R represents a halogenated alkyl group containingfrom l to 2 carbon atoms and n represents a'positive integer.
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)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US751580XA | 1953-09-16 | 1953-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2732303A true US2732303A (en) | 1956-01-24 |
Family
ID=22123939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2732303D Expired - Lifetime US2732303A (en) | 1953-09-16 | Antifoggevg and hardening agents for |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2732303A (en)) |
| BE (1) | BE531823A (en)) |
| FR (1) | FR1116147A (en)) |
| GB (1) | GB751580A (en)) |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2821546A (en) * | 1956-07-02 | 1958-01-28 | Dow Chemical Co | Polyhydric alcohol esters of 2, 2, 3-trichloropropionic acid |
| US2821545A (en) * | 1956-07-02 | 1958-01-28 | Dow Chemical Co | Polyhydric alcohol esters of 2, 2-dichlorobutyric acid |
| DE1113807B (de) * | 1959-03-07 | 1961-09-14 | Wolfen Filmfab Veb | Verfahren zum Haerten von insbesondere photographischen Gelatineschichten |
| US3006760A (en) * | 1958-10-23 | 1961-10-31 | Gen Aniline & Film Corp | Photographic materials |
| US3033680A (en) * | 1958-01-13 | 1962-05-08 | Eastman Kodak Co | Plasticized gelating compositions |
| DE1211070B (de) * | 1962-07-25 | 1966-02-17 | Eastman Kodak Co | Lichtempfindliche, photographische Silberhalogenidemulsion, die einen Haerter enthaelt |
| US3241972A (en) * | 1963-05-28 | 1966-03-22 | Eastman Kodak Co | Gelatin compositions |
| US3257208A (en) * | 1961-03-24 | 1966-06-21 | Gevaert Photo Prod Nv | Proteinaceous materials |
| US3397144A (en) * | 1967-03-21 | 1968-08-13 | Nalco Chemical Co | Control of micro-organisms in industrial process waters |
| DE1547728B1 (de) * | 1965-08-27 | 1970-12-10 | Eastman Kodak Co | Farbphotographisches Aufzeichnungsmaterial |
| US4402755A (en) * | 1979-08-14 | 1983-09-06 | Konishiroku Photo Industry Co., Ltd. | Gelatin hardening method and agents therefor |
| EP0124795A2 (en) | 1983-04-11 | 1984-11-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion |
| US4948912A (en) * | 1986-09-08 | 1990-08-14 | Southwest Research Institute | Alkylating agents and method of use thereof |
| WO2008038764A1 (fr) | 2006-09-28 | 2008-04-03 | Fujifilm Corporation | Écran à émission spontanée, procédé de fabrication d'un écran à émission spontanée, film conducteur transparent, dispositif électroluminescent, électrode transparente de cellule solaire et électrode transparente de papier électronique |
| EP2385425A1 (en) | 2010-05-07 | 2011-11-09 | Fujifilm Corporation | Silver halide photographic light-sensitive material for movie |
| WO2012035314A1 (en) | 2010-09-17 | 2012-03-22 | Fujifilm Manufacturing Europe Bv | Photographic paper |
| WO2021213762A1 (en) | 2020-04-24 | 2021-10-28 | Fujifilm Manufacturing Europe Bv | Photographic paper |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2240475A (en) * | 1940-03-02 | 1941-04-29 | Eastman Kodak Co | Photographic gelatin layer containing a polyglycerol monoester |
| US2356486A (en) * | 1943-04-15 | 1944-08-22 | Eastman Kodak Co | Stain prevention in color photography |
| US2378203A (en) * | 1944-01-13 | 1945-06-12 | Eastman Kodak Co | Ethyl trichloroacetate antifoggant |
| US2441389A (en) * | 1946-12-12 | 1948-05-11 | Du Pont | Silver halide emulsions sensitized by mixtures of high polyalkylene glycols and low polyhydric alcohols |
-
0
- US US2732303D patent/US2732303A/en not_active Expired - Lifetime
- BE BE531823D patent/BE531823A/xx unknown
-
1954
- 1954-09-14 FR FR1116147D patent/FR1116147A/fr not_active Expired
- 1954-09-16 GB GB26845/54A patent/GB751580A/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2240475A (en) * | 1940-03-02 | 1941-04-29 | Eastman Kodak Co | Photographic gelatin layer containing a polyglycerol monoester |
| US2356486A (en) * | 1943-04-15 | 1944-08-22 | Eastman Kodak Co | Stain prevention in color photography |
| US2378203A (en) * | 1944-01-13 | 1945-06-12 | Eastman Kodak Co | Ethyl trichloroacetate antifoggant |
| US2441389A (en) * | 1946-12-12 | 1948-05-11 | Du Pont | Silver halide emulsions sensitized by mixtures of high polyalkylene glycols and low polyhydric alcohols |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2821545A (en) * | 1956-07-02 | 1958-01-28 | Dow Chemical Co | Polyhydric alcohol esters of 2, 2-dichlorobutyric acid |
| US2821546A (en) * | 1956-07-02 | 1958-01-28 | Dow Chemical Co | Polyhydric alcohol esters of 2, 2, 3-trichloropropionic acid |
| US3033680A (en) * | 1958-01-13 | 1962-05-08 | Eastman Kodak Co | Plasticized gelating compositions |
| US3006760A (en) * | 1958-10-23 | 1961-10-31 | Gen Aniline & Film Corp | Photographic materials |
| DE1113807B (de) * | 1959-03-07 | 1961-09-14 | Wolfen Filmfab Veb | Verfahren zum Haerten von insbesondere photographischen Gelatineschichten |
| US3257208A (en) * | 1961-03-24 | 1966-06-21 | Gevaert Photo Prod Nv | Proteinaceous materials |
| DE1211070B (de) * | 1962-07-25 | 1966-02-17 | Eastman Kodak Co | Lichtempfindliche, photographische Silberhalogenidemulsion, die einen Haerter enthaelt |
| US3241972A (en) * | 1963-05-28 | 1966-03-22 | Eastman Kodak Co | Gelatin compositions |
| DE1547728B1 (de) * | 1965-08-27 | 1970-12-10 | Eastman Kodak Co | Farbphotographisches Aufzeichnungsmaterial |
| US3397144A (en) * | 1967-03-21 | 1968-08-13 | Nalco Chemical Co | Control of micro-organisms in industrial process waters |
| US4402755A (en) * | 1979-08-14 | 1983-09-06 | Konishiroku Photo Industry Co., Ltd. | Gelatin hardening method and agents therefor |
| EP0124795A2 (en) | 1983-04-11 | 1984-11-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion |
| US4948912A (en) * | 1986-09-08 | 1990-08-14 | Southwest Research Institute | Alkylating agents and method of use thereof |
| WO2008038764A1 (fr) | 2006-09-28 | 2008-04-03 | Fujifilm Corporation | Écran à émission spontanée, procédé de fabrication d'un écran à émission spontanée, film conducteur transparent, dispositif électroluminescent, électrode transparente de cellule solaire et électrode transparente de papier électronique |
| EP2385425A1 (en) | 2010-05-07 | 2011-11-09 | Fujifilm Corporation | Silver halide photographic light-sensitive material for movie |
| WO2012035314A1 (en) | 2010-09-17 | 2012-03-22 | Fujifilm Manufacturing Europe Bv | Photographic paper |
| WO2021213762A1 (en) | 2020-04-24 | 2021-10-28 | Fujifilm Manufacturing Europe Bv | Photographic paper |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1116147A (fr) | 1956-05-04 |
| GB751580A (en) | 1956-06-27 |
| BE531823A (en)) |
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