US2163820A - Photographic developer - Google Patents
Photographic developer Download PDFInfo
- Publication number
- US2163820A US2163820A US131780A US13178037A US2163820A US 2163820 A US2163820 A US 2163820A US 131780 A US131780 A US 131780A US 13178037 A US13178037 A US 13178037A US 2163820 A US2163820 A US 2163820A
- Authority
- US
- United States
- Prior art keywords
- group
- amino
- developer
- sodium carbonate
- developing
- 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
- -1 silver halide Chemical class 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 238000000034 method Methods 0.000 description 10
- 229910052709 silver Inorganic materials 0.000 description 9
- 239000004332 silver Substances 0.000 description 9
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000001555 benzenes Chemical class 0.000 description 5
- HORKYAIEVBUXGM-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoxaline Chemical compound C1=CC=C2NCCNC2=C1 HORKYAIEVBUXGM-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229940001482 sodium sulfite Drugs 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- CNSBIJRLKLHUIQ-UHFFFAOYSA-N 2,3-dihydro-1h-indol-5-amine Chemical class NC1=CC=C2NCCC2=C1 CNSBIJRLKLHUIQ-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SSEWGJUYSOIDMK-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinolin-6-amine Chemical class N1CCCC2=CC(N)=CC=C21 SSEWGJUYSOIDMK-UHFFFAOYSA-N 0.000 description 1
- UJZYHMZRXGNDFB-UHFFFAOYSA-N 1,3-benzothiazol-5-amine Chemical compound NC1=CC=C2SC=NC2=C1 UJZYHMZRXGNDFB-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- JYSFDZGGGCGZGO-UHFFFAOYSA-N 1-methyl-2,3-dihydroindol-5-amine Chemical compound NC1=CC=C2N(C)CCC2=C1 JYSFDZGGGCGZGO-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- VDQCQTULYAZNNT-UHFFFAOYSA-N 4-phenyl-1,2-oxazol-3-one Chemical compound O=C1NOC=C1C1=CC=CC=C1 VDQCQTULYAZNNT-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 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
- 102100038239 Protein Churchill Human genes 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- said ring member forming a hydrogenized ring Patented June 27, 1939 UNITED STATES PATENT rno'roGEArmo DEVELOPER No Drawing.
- Our present invention relates to a process of ucts develop the latent silver image in presence developing photographic silver halide emulsions and more particularly to a process in which the developing agent used is a derivative of an organic diamine, one amino-group of said diamine carrying a ring member, such as for instance CHrCHrCHr, (EH-CHz-CHz, (III-CH2. CH;'S-
- Another object of our invention relates to developing colored pictures with the aid of said compounds.
- the invention is based on the observation that v such diamines oi the benzene series are valuable developing agents in which at least one aminogroup is a member of a hydrogenized nucleus and the second amino-group is. in such a position to the other that formation of quinonoid compounds becomes possible.
- v such diamines oi the benzene series are valuable developing agents in which at least one aminogroup is a member of a hydrogenized nucleus and the second amino-group is. in such a position to the other that formation of quinonoid compounds becomes possible.
- tetrahydroquinoxaline we may use for instance tetrahydroquinoxaline:
- Samimbe'nlothiamline and substitution products thereof These odof alkali with or without a sulfite more powerfully than the known para-phenylenediamine and produce a very fine grain.
- the substances may be I used in intermixture with each other or with a known developer.
- phenyl-m'e'thyl-pyrazolone In combination with substances suitable for color development such as for instance phenyl-m'e'thyl-pyrazolone, a-hY- droxy-naphthoic' acid, phenyl-isoxazolone and the chloranilide of benzoyl acetic ester, they are also useful particularly when the amino-group is in the para-position to the nuclear amino-group fortl'fe color development of single layer or multilayer photographic material.
- substances suitable for color development such as for instance phenyl-m'e'thyl-pyrazolone, a-hY- droxy-naphthoic' acid, phenyl-isoxazolone and the chloranilide of benzoyl acetic ester
- Example 1 A developer suitable for very fine grain work consists of the following solution: I
- the developer according to Example 3 produces in addition to'the silver image a dyestufi image 7 in blue-red, from which by means of a suitable ,Water cubic-centimeters 100 v Tetrahydroquinoxaline "grains" 1.5 Calcined sodium carbonate do 3 Anhydrous sodium sulfite do.. 3
- Example 3 ZWater cubic centimeters 100 6-amino-8-methoxy l,2,3,4-tetrahydroquinaldine gram 1 Calcined sodium carbonate gramsu 3 1-phenyl-3-methyl-5-pyrazolonegram; 0.5
- Example 4 Water cubic centimeters' 100 5-amino-dihydromethylindole gram 1 Calcined sodium carbonate grams 3 Anhydrous sodium sulfite do 3 H
- Example 5 I Water; cubic centimeters 100 Calcined sodium carbonate grams I 3 5-aminobenzothiazoline gram 1
- Our invention is not limited to the examples given, but we contemplate as included all such modifications and equivalents specification.
- a 3- color image can be produced by development either by the negative process or by the reversal process, the image being in complementary colors in the first case and in correct colors in the secondcase.
- the methylene group or groups concerned in the ring formation may carry substituents which may be of a character suitable for lending solubility to the developer, such as for instance the hydroxy group and hydroxy-ethyl group.
- a process of developing photographic silver halide emulsions which comprises treating the said material in an aqueous solution of tetrahydroquinoxaline sodium carbonate and sodium sufite.
- a process of developing photographic silver halide emulsions which comprises treating the said material in an aqueous solution of B-amino- 8 methoxy 1,2,3,4-tetrahydroquinoline, sodium carbonate and sodium sulfite.
- a process of developing photographic silver halide emulsions which comprises treating the said material in an aqueous solution of 6-amino-8 methoxy 1,2,3,4 tetrahydroquinaldine, sodium carbonate and l-phenyl-3-methyl-pyrazolone.
- composition of matter a photographic developer containing tetrahydroquinoxaline sodium carbonate and sodium sulfite.
- composition of matter a photographic developer containing 6-amino-8-methoxy-1,2,13,4- tetrahydroquinoline sodium carbonate and sodium sulfite.
- composition of matter a photographic developer containing 6-amino-8-methoxy-1,23,4- tetrahydroquinaldine sodium carbonate and 1- phenyI-B-methyl-pyrazolone.
- a process of developing photographic silver halide emulsions which comprises treating said emulsions in a bath containing a heterocyclic diamine of the benzene series hydrogenized in the heterocyclic nucleus selected from the group consisting of 5-aminodihydroindoles, G-aminotetrahydroquinolines, '5-aminobenzothiazolines, tetrahydroquinoxalines, and alkyland oxalkyl substitution products thereof.
- composition of matter a photographic developer containing an alkali metal sulfite, an alkali metal carbonate and a heterocyclic diamine of the benzene series hydrogenized in the heterocyclic nucleus, said diamine being selected from the group consisting of 5-aminodihydroindoles, 6- aminotetrahydroquinolines, fi-aminobenzothiazolines, tetrahydroquinoxalines, and alkyland oxalkyl substitution products thereof.
- composition of matter a photographic developer for color forming development containing an alkali metal sulfite, an alkali metal carbonwherein Y is selected from the group consisting of -CH2CH2, -CH2, S;
- Z is a member of the group consisting of H
- ,R1 is a member of the group consisting of -CHs
- said developer being capable of forming a dyestuff with a dyestuff component for color forming development.
- a process of developing silver halide emulsions which comprises treating said material in a bath containing a diamine of the benzene series corresponding to the following general formula wherein Y is a member of the group consisting of CH2- CH2, CH2, S;
- Z is a member of the group consisting of H
- R1 is a member of the group consisting of CH3,
- a process of developing silver halide emulsions which comprises treating said material in a bath containing a diamine of the benzene series corresponding to the following general formula Y Haw-W wherein said diamine being used in combination with a dyestufi component for color forming development.
- composition of matter a photographic developer comprising an alkali metal sulfite, an alkali metal carbonate and a compound cor- .
- Y is a member of the group consisting of CH2- CH2, CH2, S;
- Z is a member of the group consisting of H
- R1 is a member of the group consisting of CH3.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI0054850 | 1936-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2163820A true US2163820A (en) | 1939-06-27 |
Family
ID=7193989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US131780A Expired - Lifetime US2163820A (en) | 1936-04-23 | 1937-03-19 | Photographic developer |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2163820A (xx) |
| BE (1) | BE421135A (xx) |
| FR (1) | FR820865A (xx) |
| GB (1) | GB478345A (xx) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2566259A (en) * | 1948-09-25 | 1951-08-28 | Eastman Kodak Co | 8-alkyl sulfonamidoethyl-n-substituted saturated heterocyclic developers |
| US2596978A (en) * | 1947-09-17 | 1952-05-20 | Searle & Co | 8-hydroxy-1, 2, 3, 4-tetrahydroquinoline as a silver halide developer |
| US3970454A (en) * | 1974-01-10 | 1976-07-20 | Eastman Kodak Company | Photographic developing agents |
| US4845019A (en) * | 1986-06-06 | 1989-07-04 | Visicon Laboratories, Inc. | Method for exposing and developing photosensitive materials |
-
0
- BE BE421135D patent/BE421135A/xx unknown
-
1936
- 1936-05-11 GB GB13279/36A patent/GB478345A/en not_active Expired
-
1937
- 1937-03-19 US US131780A patent/US2163820A/en not_active Expired - Lifetime
- 1937-04-20 FR FR820865D patent/FR820865A/fr not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2596978A (en) * | 1947-09-17 | 1952-05-20 | Searle & Co | 8-hydroxy-1, 2, 3, 4-tetrahydroquinoline as a silver halide developer |
| US2566259A (en) * | 1948-09-25 | 1951-08-28 | Eastman Kodak Co | 8-alkyl sulfonamidoethyl-n-substituted saturated heterocyclic developers |
| US3970454A (en) * | 1974-01-10 | 1976-07-20 | Eastman Kodak Company | Photographic developing agents |
| US4845019A (en) * | 1986-06-06 | 1989-07-04 | Visicon Laboratories, Inc. | Method for exposing and developing photosensitive materials |
Also Published As
| Publication number | Publication date |
|---|---|
| BE421135A (xx) | |
| FR820865A (fr) | 1937-11-20 |
| GB478345A (en) | 1938-01-11 |
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