US2527379A - Silver halide developers for the production of azine dyestuff images - Google Patents
Silver halide developers for the production of azine dyestuff images Download PDFInfo
- Publication number
- US2527379A US2527379A US38948A US3894848A US2527379A US 2527379 A US2527379 A US 2527379A US 38948 A US38948 A US 38948A US 3894848 A US3894848 A US 3894848A US 2527379 A US2527379 A US 2527379A
- Authority
- US
- United States
- Prior art keywords
- developer
- color
- silver halide
- development
- azine
- 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
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- -1 Silver halide Chemical class 0.000 title claims description 73
- 229910052709 silver Inorganic materials 0.000 title claims description 35
- 239000004332 silver Substances 0.000 title claims description 35
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 33
- 239000000975 dye Substances 0.000 title description 31
- 238000004519 manufacturing process Methods 0.000 title description 10
- 238000011161 development Methods 0.000 claims description 27
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- 239000000839 emulsion Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 238000010186 staining Methods 0.000 claims description 3
- 230000018109 developmental process Effects 0.000 description 25
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 12
- 239000002253 acid Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 235000010265 sodium sulphite Nutrition 0.000 description 6
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 241001024304 Mino Species 0.000 description 2
- QMJDEXCUIQJLGO-UHFFFAOYSA-N [4-(methylamino)phenyl] hydrogen sulfate Chemical compound CNC1=CC=C(OS(O)(=O)=O)C=C1 QMJDEXCUIQJLGO-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000003287 bathing Methods 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 2
- 235000019801 trisodium phosphate Nutrition 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- KJMJXENEXMKOAA-UHFFFAOYSA-N 4-anilino-2,4-dioxobutane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(=O)CC(=O)NC1=CC=CC=C1 KJMJXENEXMKOAA-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 125000005026 carboxyaryl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001143 conditioned 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
- 150000004985 diamines Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- AXKVOSSFZLZIDC-UHFFFAOYSA-N n,n-diaminoaniline Chemical compound NN(N)C1=CC=CC=C1 AXKVOSSFZLZIDC-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940075581 sodium bromide Drugs 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- 125000005425 toluyl 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
- G03C7/32—Colour coupling substances
- G03C7/3244—Couplers forming azinic dyes; Specific developers therefor
Definitions
- the present invention relates to the production of azine dye images and more particularly to color developers designed to yield such images of good gradation and dye density and free from color fog.
- an aromatic primary amine is employed to reduce an exposed silver halide image to metallic silver,"the amine being thereb oxidized to a component which couples with a color former to produce a dyestuff image in situ with the metallic silver image.
- the developer an NN-dialkylated-pphenylene diamine.
- Such developers have been used for development of a latent image as well as for the development of a residual silver halide image in the reversal process.
- azine dye images can be obtained by developing an exposed silver halide emulsion with developers of the 2.4-diamino aniline type, and particularly those of the class of the N-substituted 4.6-diamino metanilic acids.
- the azine dye images which result from this method are much more stable to acids, alkalies and alkaline oxidation than are the azo halide which does not azine dye forming color developers.
- getic latent image developers contemplated herein are those generally referred to in color photography as silver developers or black and white ⁇ developers.
- the partial development effected by the energetic latent image developer may be realizedby bathing the exposed silver halide in such a developer for a short period of time and then de- ⁇ between the energetic latent image developer andthe color developer has not been ascertained. It was our original theor that the energetic. latent image developer operated as a catalyst on accelerator for the color developer in the devel opment of a latent image. This theory, however, would not explain the fact that the film can be washed for hour or longer after an extremely shorttreatment with the energetic developer and the latent image still be capable of being com: pletely developed by the color developer.
- diamino aniline developers of nitrogenous bases such as ethylenediamine, benzylamine, quinoline, and the like.
- azine dye images can be uniforml and energetically effected while obtaining improved color rendition'and substantiallyno color fog bycarry ing out the development in part with an energetic to improve the azine dye images obtained by c01 or development with an azine dye-forming color developer by adding to the developer an energetic latent image developer;
- a further object of the present invention is to produce azine dye images which have improved latent image developer ior the exposed silver color rendition and freedom from color fog by developing an exposed silver halide emulsion in the presence of a color formerwith a 4.6-diamino metanilic acid developer containing an en ergetic latent image developer.
- Compounds which may be used as the color developer in producing the azine dye images are of the 2.4-diaminoaniline type and are more particularly those having the formula:
- R is hydrogen or alkyl, i. e., methyl, ethyl, propyl, butyl, amyl or the like
- R1' is an aliphatic radical such as alkyl .as-above, carboxy alkyl such as carboxy methyl, carboxy ethyl and the like, hydroxy alkyl such as hydroxyethyl, hydroxy propyl and the like, sulfo alkyl such as sulfomethyl, sulfopropyl, sulfobutyl and the like, or an aromatic radical such as aryl, i.
- hydroxy alkoxy aryl such as hydroxy methoxy phenyl, hydroxy ethoxy phenyl and the like
- R2 is an aromatic or aliphatic radical as illustrated above
- X and Y are hydrogen, alkyl as above, sulfo or carboxy, or together represent the atoms necessary to complete a six-membered isocyclic ring system such as benzo and the like.
- thecompounds which are utilized are the N- substituted 4.6-diamino metanilic acids, in which case Y is hydrogen, and X is sulfo.
- Examples of such mixtures are:-.4-(;3- hydroxyethylamino) 6 phenylamino-metanilic acid with 4-methylamino-6sphenylamino-metanilic acid, 4.6-bis-(phenylamino) -metanilic acid with 4.6-bis-(methylamino) -metanil ic' acid.
- the developer components listed above may be prepared by the method described in the a'fore- -:i
- aforementioned color developers in order toeif e'c't' the desired"'mo're energetic development are p-amino phenol, p-(N-methylamino) -phen ol or a mixture thereofwith hydro'duinone, 2.4-diamino phenol and ca'techoL-g I I
- the development time with the former will depend on the characteristics of the developer chosen, but should not exceed one-half the'time' which is necessary to develop the silver image to maximum contrast.
- the exposed silver halide is so conditioned that it'becomes readily amenable to the production of azine dye images with the aforesaid color developers irrespective of the energy of said developers as measured by their effect on a latent silver halide image.
- the quantity of the former used will in no case exceed the quantity by weight of the active color developer ingredient and will dependfirst upon the particular energetic or black and white developer employed, and, second, upon th type of processing involved, 1. e., whether negative or positive. Generally speaking, the more vigorous the developing substance the smaller th amount required to produce the desired effect. Similarly where the processing is by the reversal method, a smaller quantity is usedthan where the processing involves negative development. In any case'good resultsare obtained when the concentration of energetic or black and white developer rangesfrom- .5 to 4 grams per liter of developer. Within the aforestated range an amount of .5 to 1.5.
- azine dyesythe quantity of the energetic or black and white developer employed generally ranges from 2 to 4 grams per liter.
- the process utilizing the developer :composi-- tions contemplated herein may be effected in various ways.
- the color-forming component may be located in the developer.
- the color former in non-diffusing form may be located in the emulsion.
- 'Multilayer film, each layer containing a non-difiusing color former, may be used and the film developed to the desired subtractive azine dye images in a single color forming development step while :utilizing such developer compositions.
- the developers in addition to the components previously mentioned, also contain an alkali such as sodium carbonate, sodium'hydroxide, and the like.
- the developers will also contain the usual adjuncts such as an alkali metal bromide, i.-e., potassium bromide, sodiumbromide and the like, and an alkali metal sulfite such'as sodium sulfite and the like.
- an alkali metal bromide i.-e., potassium bromide, sodiumbromide and the like
- an alkali metal sulfite such'as sodium sulfite and the like.
- a coupling aid in the form of an organic base such as pyridine, quinoline, ethylenediamine and the like.
- Example I 4-methylamino -;'6 ⁇ phenylamino-metanilic acid grams 6 2.4-diamino phenol d 1 Sodium sulfite do 60 Ethylenediamine r cc 30 Water cc "1000 The film after development is bleached'with'a ferricyanide bleach and. fixed in an acid-hardening hypo solution. There is thus obtained- .a magenta azine :dye-image of good gradationin which the whites are perfectly clear.
- Example II The procedure is the same as that of Example I excepting that the 2.4-diaminophenol is replaced by 1.5 grams of p-amino phenol per liter. of developer.
- Example III A bi-pack having ared sensitive'silver bromide emulsion containing asthe cyan colorformer a compound of the followingconstitution:
- Example IV A photographic silver bromide emulsion is exposed'and the latent image developed to a negative silverimage. The residual silver halide is re-exposed and developed in a developer of the following composition:
- Example V The -bi-pack referred to in Example .111 is exposed and developed for 15 minutes in a solution of the followingcomposition:
- Example VI A photographic silver halide emulsion layer containing an azine color former in non-diffusing form as given in Example III is exposed. It is given a short development (30 to 90 seconds) in a conventional metol-hydroquinone developer. Thereafter it is thoroughly washed for 15 minutes and the development is continued in an azine color forming developer of the following composition:
- R is selected from the class consisting of hydrogen and alkyl
- R1 is selected from the class consisting of aliphatic and aromatic radicals
- R2 is selected from the class consisting of aromatic radicals, a ring carbon atom of which is directly linked to the nitrogen atom, and aliphatic radicals a carbon atom of which is directly linked to the nitrogen atom, said carbon atom being substituted by at least two hydrogen atoms
- X and Y are selected from the 10 class consisting of hydrogen, alkyl, sulfo and carboxy
- Q represents the atoms necessary to complete a six-membered isocyclic ring system.
- a photographic developer for the production of azine dye images having high color rendition and free from color fog comprising an aqueous alkaline solution of a non-staining silver image developer and as the color forming developer a compound selected from the class consisting of those of the following formulae:
- R is selected from the class consisting of hydrogen and alkyl
- R1 is selected from the class consisting of hydrogen, aliphatic and aromatic radicals
- R2 is selected from the class consisting of aromatic radicals, a ring carbon atom of which is directly linked to the nitrogen atom, and aliphatic radicals a carbon atom of which is directly linked to the nitrogen atom, said carbon atom being substituted by at least two hydrogen atoms
- X and Y are selected from the class consisting of hydrogen, sulfo and carboxy
- Q represents the atoms necessary to complete a six-membered isocyclic ring system.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE490161D BE490161A (en)) | 1948-07-15 | ||
| US38948A US2527379A (en) | 1948-07-15 | 1948-07-15 | Silver halide developers for the production of azine dyestuff images |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38948A US2527379A (en) | 1948-07-15 | 1948-07-15 | Silver halide developers for the production of azine dyestuff images |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2527379A true US2527379A (en) | 1950-10-24 |
Family
ID=21902839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US38948A Expired - Lifetime US2527379A (en) | 1948-07-15 | 1948-07-15 | Silver halide developers for the production of azine dyestuff images |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2527379A (en)) |
| BE (1) | BE490161A (en)) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2656272A (en) * | 1950-11-30 | 1953-10-20 | Gen Aniline & Film Corp | Stabilized azine photographic developers containing sodium metaborate as the sole alkali |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1954335A (en) * | 1931-10-29 | 1934-04-10 | Eastman Kodak Co | Control of contrast with color developers |
| US2301387A (en) * | 1939-12-09 | 1942-11-10 | Eastman Kodak Co | Reducing aerial oxidation of photographic developers |
| US2414491A (en) * | 1945-01-27 | 1947-01-21 | Gen Aniline & Film Corp | Photographic developer |
| US2417514A (en) * | 1940-09-23 | 1947-03-18 | Spectrum Products Company Inc | Method and means for producing colored photographic images |
| US2449919A (en) * | 1947-07-05 | 1948-09-21 | Eastman Kodak Co | 3-methylsulfonamido-4-amino dimethyl aniline photographic developer |
-
0
- BE BE490161D patent/BE490161A/xx unknown
-
1948
- 1948-07-15 US US38948A patent/US2527379A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1954335A (en) * | 1931-10-29 | 1934-04-10 | Eastman Kodak Co | Control of contrast with color developers |
| US2301387A (en) * | 1939-12-09 | 1942-11-10 | Eastman Kodak Co | Reducing aerial oxidation of photographic developers |
| US2417514A (en) * | 1940-09-23 | 1947-03-18 | Spectrum Products Company Inc | Method and means for producing colored photographic images |
| US2414491A (en) * | 1945-01-27 | 1947-01-21 | Gen Aniline & Film Corp | Photographic developer |
| US2449919A (en) * | 1947-07-05 | 1948-09-21 | Eastman Kodak Co | 3-methylsulfonamido-4-amino dimethyl aniline photographic developer |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2656272A (en) * | 1950-11-30 | 1953-10-20 | Gen Aniline & Film Corp | Stabilized azine photographic developers containing sodium metaborate as the sole alkali |
Also Published As
| Publication number | Publication date |
|---|---|
| BE490161A (en)) |
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