US2695234A - Photographic development - Google Patents
Photographic development Download PDFInfo
- Publication number
- US2695234A US2695234A US267496A US26749652A US2695234A US 2695234 A US2695234 A US 2695234A US 267496 A US267496 A US 267496A US 26749652 A US26749652 A US 26749652A US 2695234 A US2695234 A US 2695234A
- Authority
- US
- United States
- Prior art keywords
- water
- developing
- formula
- image
- photographic
- 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 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 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 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 18
- 125000003277 amino group Chemical group 0.000 description 15
- 229910052709 silver Inorganic materials 0.000 description 15
- 239000004332 silver Substances 0.000 description 15
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- -1 mono-ethyl-p-phenylene Chemical group 0.000 description 11
- 239000004215 Carbon black (E152) Substances 0.000 description 10
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 10
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 4
- 229960003868 paraldehyde Drugs 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- CYXJEHCKVOQFOV-UHFFFAOYSA-N (4-amino-2-methylphenyl) hydrogen sulfate Chemical compound CC1=CC(N)=CC=C1OS(O)(=O)=O CYXJEHCKVOQFOV-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
- TVOSOIXYPHKEAR-UHFFFAOYSA-N 4-piperidin-1-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCCCC1 TVOSOIXYPHKEAR-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010028164 Multiple allergies Diseases 0.000 description 1
- LUTSRLYCMSCGCS-BWOMAWGNSA-N [(3s,8r,9s,10r,13s)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC=C3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 LUTSRLYCMSCGCS-BWOMAWGNSA-N 0.000 description 1
- MPLZNPZPPXERDA-UHFFFAOYSA-N [4-(diethylamino)-2-methylphenyl]azanium;chloride Chemical compound [Cl-].CC[NH+](CC)C1=CC=C(N)C(C)=C1 MPLZNPZPPXERDA-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- IOUVKUPGCMBWBT-QNDFHXLGSA-N phlorizin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 IOUVKUPGCMBWBT-QNDFHXLGSA-N 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000837 restrainer Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/407—Development processes or agents therefor
- G03C7/413—Developers
- G03C7/4136—Developers p-Phenylenediamine or derivatives thereof
Definitions
- This invention relates .to a photographic developing process and to photographic developers, especially for use in color photography.
- the p-phenylene diamines which are used as color developing agents "have a number of drawbacks. 'They are highly allergic to :the skin. Developing solutions which contain p-p'henylene diamines darken which is due to oxidation "by air, and at thesame'time the potency-of the solution is diminished.
- the developing agents according teaur invention produce on color development the same dyestuif as the developingagents of the formula Y-Ar-NHz since the group CZZSOsM is split oil. This fact facilitates considerably the replacement of compounds of the formula Y-Ar-NHz by corresponding compounds of Formula II.
- A is a divalent hydrocarbon nucleus
- X'Tis COOM or fiSOsM wherein M is hydrogen or a water-soluble salt-forming cation, preferably an alkali metal such as sodium or potassium
- Y is -OH, NH2, NHR or --NR2 in ortho- .,or para-position to the nitrogen atom (wherein R is a hydrocarbon radical).
- veloping agent a buffering agent as, for instance, di-
- the solution may be composed before use from two or more solutions, concentrated solutions, or powders.
- the developing agents may be added to the photographic materialas well. Inthis' case'pthe material may 'beydeveloped, after-exposure, in an alkaline solution;
- Example 1 To a solution :of 4.4 .g. acetaldehyde in 40 gram. water are added, while cooling in ice, 20 g. sodium bisulphite. After also adding 16.4 g. NzN-diethyl-p-phenylene diamine, the mixture is heated on the water bath for 13 minutes, while shaking. After cooling, the crystals formed are sucked off and purified bycrystallization from water. -Melting :po'int: 143-145 .C. The product .obtained corresponds :to the following probable formula:
- tggether may-eomplete a heterocyclig: 'nu'cleusyoptjonal'l y substituted, e. g.,-by-a hydroxyl-or a 'su'lpho group); and Z-and Z are hydrogen or alkyl' or substituted alkyl.
- N--- I H--C H-S 03H C2115 CHz-CHr-S OaNB
- Example 4 Example 5 11.5 g. dry sodium bisulphite and 3.5 g. croton aldehyde are dissolved in 40 com. water by heating. After cooling, the solution is shaken with 9.9 g. N:N-diethylp-phenylene diamine for 4 hours and next concentrated in vacuo. The precipitate formed is sucked off and washed with acetone. Melting point: above 330 C. The product obtained corresponds to the following probable formula:
- Example 6 15.9 g. dry sodium bisulphite and 11 g. iso-butyric aldehyde are dissolved in 40 com. water by heating on the water bath. To this solution is added a solution of 32 g. NzN-diethyl-p-phenylene diamine sulphate in 100 com. water, and the whole is heated for 2 hours on the water bath. Crystals form which after cooling are sucked off and recrystallized from water. Melting point: 136-139" C. The product obtained corresponds to the following probable formula:
- Example 8 2.2 g. paraldehyde are dissolved in a solution of 5.2 g. dry sodium bisulphite in 30 com. water. After heating for 2 hours on the water bath with 11.5 g. N-ethyl- N-beta-hydroxy ethyl-p-phenylene diamine sulphate, and after cooling, the precipitate formed is sucked oif, washed with acetone and recrystallized from water.
- Example 9 5.2 g. dry sodium bisulphite and 2.2 g. paraldehyde are dissolved in 30 com. water and heated for 2 hours on the water bath with 10.7 g. 2-amino5-diethylaminotoluene hydrochloride. After cooling, the precipitate formed is sucked off and washed with acetone. Melting point: 135-l38 C.
- the product obtained corresponds to the following probable formula:
- Example 11 2.8 g. dry sodium bisulphite dissolved in 10 ccm. water and 2.5 ccm. of an aqueous solution of formaldehyde 36% are heated for 15 minutes at 40-50 C. with 3.5 g. sodium bicarbonate and 5.4 g. N-methyl-6'aminotetra-hydroquincline-oxalate in com. water. The precipitate formed is sucked off and recrystallized from diluted alcohol. Melting point: 149l50 C. The product obtained corresponds to the following probable orrnu a:
- Example I 2 0.5 g. paraldehyde and 1.25 g. dry sodium bisulphite are dissolved in 10 com. water and heated for 2 hours on the water bath with 2.1 g. N-(p-aminophenyl)- piperidine. After cooling, the precipitate formed is sucked off and recrystallized from water. Melting point: 139 C.
- the product obtained corresponds to the following probable formula:
- a developing substance according to Examples 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 Metol (methyl-para-aminophenol-sulphate) 2 Sodium sulphite (cryst.) Trisodium phosphate 3.5 Potassium bromide 1.
- gelatine also collodion, a water-permeable cellulose ester, or another water-permeable synthetic resin may be used as a binding agent for the silver halide.
- Example 14 A silver halide gelatine emulsion layer, after exposure, is developed in a bath of the following composition:
- Example I5 A multi-layer material comprising;
- a color developing substance according to Examples 1, 2, 3, 4,5,6, 8, 9, 10, 11 or 12 Sodium sulphite (cryst.) 5 Potassium carbonate 75 Potassium bromide 2.5
- Example 16 A photographic multi-layer material as described in Example 15, containing sensitizers and color couplers fast to difiusion, may after exposure be directly developed in the above mentioned color developing bath and further treated as in Example 15. The negative color image obtained may be copied upon similar multi-layer material, and by treatment in a like manner as to obtain the negative, a positive copy image is obtained.
- Process for developing a reducible silver salt image in a photographic silver halide emulsion layer, WhlCh comprises treating such layer with a developer containing a compound according to the formula:
- M is a member selected from the group consisting of hydrogen and a water-soluble salt-forming cation
- Ar is p-phenylene
- Y is a substituent of Ar 1n para-position to the nitrogen atom, selected from the group consisting of an amino group substituted by a hydrocarbon radical, an amino group subst tuted by two hydrocarbon radicals, an amino group substituted by two substituents completing together a heterocyclic radical, and an amino group substituted by a substituent linked to the carbon atom in ortho-position to Y
- Z and Z' are members selected from the group consisting of hydrogen and alkyl.
- J6 'QJTroeess'for forming a colored image by developing a reducible silver salt image in a photographic silver halide emulsion layer which comprises treating such layer with a developer containing arcompound according wherein .M :Jis auznentlber :selected from the :group :consisting of hydrogen and a water-soluble salt forming cation;
- Ar is p-phenylene;
- Y is a substituent of Ar in para-position to the nitrogen atom, selected from the group consisting ofan' amino groupsfibstituted by a hydrocarbon radical, an amino group substituted by two hydrocarbon radicals, an amino group substituted by two substituents completing together a heterocyclic radical, and an amino group substituted by a substituent linked to the carbon atom in ortho-position to Y;
- Z and Z are members selected from the-group consisting of hydrogen and alkyl.
- Process for forming a colored image by developing a reducible silver salt image in a photographic silver halide emulsion layer which comprises treating such layer with a developer containing a compound according to the formula:
- Process for forming a colored image by developing a reducible silver salt image in a photographic silver halide emulsion layer which comprises treating such layer with a developer containing a compound according to the formula:
- M is a member selected from the group consisting of hydrogen and a water-soluble salt-forming cation
- Ar is p-phenylene
- Y is a substituent of Ar in para-position to the nitrogen atom, selected from the group consisting of an amino group substituted by a hydrocarbon radical, an amino group substituted by two hydrocarbon radicals, an amino group substituted by two substituents completing together a heterocyclic radical, and an amino group substituted by a substituent linked to the carbon atom in ortho-position to Y
- Z and Z are members selected from the group consisting of hydrogen and alkyl.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2093/51A GB691815A (en) | 1951-01-26 | 1951-01-26 | Improvements in or relating to photographic development |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2695234A true US2695234A (en) | 1954-11-23 |
Family
ID=9733470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US267496A Expired - Lifetime US2695234A (en) | 1951-01-26 | 1952-01-21 | Photographic development |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2695234A (fr) |
| BE (1) | BE508676A (fr) |
| CH (1) | CH298157A (fr) |
| DE (1) | DE926713C (fr) |
| FR (1) | FR1049864A (fr) |
| GB (1) | GB691815A (fr) |
| NL (1) | NL83481C (fr) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2879160A (en) * | 1954-09-09 | 1959-03-24 | Antioch College Of Yellow Spri | Composition for developing surface disturbances on a photographic film |
| US3342599A (en) * | 1965-06-07 | 1967-09-19 | Eastman Kodak Co | Schiff base developing agent precursors |
| US3647462A (en) * | 1969-02-19 | 1972-03-07 | Eastman Kodak Co | Methods and materials for replenishment of developers for color photographic films (b) |
| US3647461A (en) * | 1969-02-19 | 1972-03-07 | Eastman Kodak Co | Methods and materials for replenishment of developers for color photographic films |
| EP0143570A2 (fr) | 1983-11-02 | 1985-06-05 | Konica Corporation | Matériau photographique couleur à l'halogénure d'argent |
| US6057090A (en) * | 1995-09-21 | 2000-05-02 | Fuji Photo Film Co., Ltd. | Silver halide photographic material and hydroxamic acid-based compound used therefor |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2163166A (en) * | 1936-05-27 | 1939-06-20 | Agfa Ansco Corp | Photographic developer |
| US2570116A (en) * | 1946-01-10 | 1951-10-02 | Gen Aniline & Film Corp | Color developers for the production of azine dye images |
| US2575027A (en) * | 1949-10-29 | 1951-11-13 | Gen Aniline & Film Corp | N-substituted 4, 6-diamino metanilic acids |
| US2578292A (en) * | 1950-02-17 | 1951-12-11 | Eastman Kodak Co | Disodium-n, n'-dimethyl-p-phenylene-diaminomethane sulfonate and process for preparation |
-
0
- NL NL83481D patent/NL83481C/xx active
- BE BE508676D patent/BE508676A/xx unknown
-
1951
- 1951-01-26 GB GB2093/51A patent/GB691815A/en not_active Expired
-
1952
- 1952-01-19 CH CH298157D patent/CH298157A/fr unknown
- 1952-01-21 US US267496A patent/US2695234A/en not_active Expired - Lifetime
- 1952-01-25 FR FR1049864D patent/FR1049864A/fr not_active Expired
- 1952-01-26 DE DEG8015A patent/DE926713C/de not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2163166A (en) * | 1936-05-27 | 1939-06-20 | Agfa Ansco Corp | Photographic developer |
| US2570116A (en) * | 1946-01-10 | 1951-10-02 | Gen Aniline & Film Corp | Color developers for the production of azine dye images |
| US2575027A (en) * | 1949-10-29 | 1951-11-13 | Gen Aniline & Film Corp | N-substituted 4, 6-diamino metanilic acids |
| US2578292A (en) * | 1950-02-17 | 1951-12-11 | Eastman Kodak Co | Disodium-n, n'-dimethyl-p-phenylene-diaminomethane sulfonate and process for preparation |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2879160A (en) * | 1954-09-09 | 1959-03-24 | Antioch College Of Yellow Spri | Composition for developing surface disturbances on a photographic film |
| US3342599A (en) * | 1965-06-07 | 1967-09-19 | Eastman Kodak Co | Schiff base developing agent precursors |
| US3647462A (en) * | 1969-02-19 | 1972-03-07 | Eastman Kodak Co | Methods and materials for replenishment of developers for color photographic films (b) |
| US3647461A (en) * | 1969-02-19 | 1972-03-07 | Eastman Kodak Co | Methods and materials for replenishment of developers for color photographic films |
| EP0143570A2 (fr) | 1983-11-02 | 1985-06-05 | Konica Corporation | Matériau photographique couleur à l'halogénure d'argent |
| US6057090A (en) * | 1995-09-21 | 2000-05-02 | Fuji Photo Film Co., Ltd. | Silver halide photographic material and hydroxamic acid-based compound used therefor |
| US6433223B1 (en) | 1995-09-21 | 2002-08-13 | Fuji Photo Film Co., Ltd. | Silver halide photographic material and hydroxamic acid-based compounds used therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| NL83481C (fr) | |
| CH298157A (fr) | 1954-04-30 |
| DE926713C (de) | 1955-04-21 |
| GB691815A (en) | 1953-05-20 |
| BE508676A (fr) | |
| FR1049864A (fr) | 1954-01-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2592364A (en) | p-phenylenediamine developer containing alkylacylamidoethyl or alkylacylamidoethoxyring substituents | |
| US4126461A (en) | Black-and-white photographic elements and processes | |
| DE2362752C2 (de) | Einen photographischen Entwicklungsinhibitor abspaltende Verbindung und ihre Verwendung | |
| US3226232A (en) | Fog reduction in silver halide emulsions with a diphenyldisulfide dicarboxylic acid | |
| US3221023A (en) | (2-hydroxymethyl-3-pyrazolidones) | |
| US2695234A (en) | Photographic development | |
| US2412700A (en) | Thioglycolic amides | |
| US3013879A (en) | Production of color photographic images | |
| US3932480A (en) | Benzylthiosulfuric acid salts | |
| US2453661A (en) | Colored couplers | |
| US2455170A (en) | Colored couplers | |
| US3245788A (en) | Production of color photographic images | |
| US4012258A (en) | Process for forming color photographic images | |
| US3222176A (en) | Photographic colour images from amino substituted phenols | |
| US3677764A (en) | Silver halide emulsion containing purple coupler for color photography and process of making the same | |
| US2673801A (en) | Production of color photographic images | |
| DE1146751B (de) | Verfahren zur Herstellung von direktpositiven Farbstoffbildern | |
| US2668112A (en) | Manufacture of photographic color images | |
| US2551134A (en) | Process of color developing with 2-thiohydantoin derivatives | |
| US2979405A (en) | Light-sensitive photographic element containing a 1-hydroxy-2-naphthoic acid anilidecolor coupler | |
| US2680730A (en) | Acetals of polyhydric alcohols | |
| US2448939A (en) | Thioglycolic amide couplers | |
| US3265499A (en) | Photographic developing compositions | |
| US2897079A (en) | Production of colored photographic images with oxodiazole couplers | |
| US3471295A (en) | Production of colored direct-positive images |