US2525503A - Production of phenazonium dyestuff images - Google Patents
Production of phenazonium dyestuff images Download PDFInfo
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- US2525503A US2525503A US793535A US79353547A US2525503A US 2525503 A US2525503 A US 2525503A US 793535 A US793535 A US 793535A US 79353547 A US79353547 A US 79353547A US 2525503 A US2525503 A US 2525503A
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- Prior art keywords
- naphthol
- phenazonium
- color
- images
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- Prior art date
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- 239000000975 dye Substances 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 6
- -1 SILVER HALIDE Chemical class 0.000 claims description 17
- 239000000839 emulsion Substances 0.000 claims description 13
- 229910052709 silver Inorganic materials 0.000 claims description 11
- 239000004332 silver Substances 0.000 claims description 11
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 8
- 238000011161 development Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229950011260 betanaphthol Drugs 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000004442 acylamino group Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IKBZDUVFMIFABY-UHFFFAOYSA-N 3-anilinonaphthalen-2-ol Chemical compound OC1=CC2=CC=CC=C2C=C1NC1=CC=CC=C1 IKBZDUVFMIFABY-UHFFFAOYSA-N 0.000 description 2
- WSUYONLKFXZZRV-UHFFFAOYSA-N 7-aminonaphthalen-2-ol Chemical compound C1=CC(O)=CC2=CC(N)=CC=C21 WSUYONLKFXZZRV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 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 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- JRJDQVYOBXLVHB-UHFFFAOYSA-N 7-(ethylamino)naphthalen-2-ol Chemical compound C(C)NC1=CC=C2C=CC(=CC2=C1)O JRJDQVYOBXLVHB-UHFFFAOYSA-N 0.000 description 1
- LEOIWDTYJPJLPS-UHFFFAOYSA-N 7-anilinonaphthalen-2-ol Chemical compound N(C1=CC=CC=C1)C1=CC=C2C=CC(=CC2=C1)O LEOIWDTYJPJLPS-UHFFFAOYSA-N 0.000 description 1
- AMSZDZSPUNARKZ-UHFFFAOYSA-N 8-amino-5-chloronaphthalen-2-ol Chemical compound ClC1=C2C=CC(=CC2=C(C=C1)N)O AMSZDZSPUNARKZ-UHFFFAOYSA-N 0.000 description 1
- 244000186140 Asperula odorata Species 0.000 description 1
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000070928 Calligonum comosum Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000008526 Galium odoratum Nutrition 0.000 description 1
- VYKVZMXVIKWGQV-UHFFFAOYSA-N N-(7-hydroxynaphthalen-2-yl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C2C=CC(=CC2=C1)O VYKVZMXVIKWGQV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- BWGYGWYDRUDOSS-UHFFFAOYSA-N n-(6-hydroxynaphthalen-1-yl)acetamide Chemical compound OC1=CC=C2C(NC(=O)C)=CC=CC2=C1 BWGYGWYDRUDOSS-UHFFFAOYSA-N 0.000 description 1
- CEJJPMISDMYGKE-UHFFFAOYSA-N n-(7-hydroxynaphthalen-2-yl)acetamide Chemical compound C1=CC(O)=CC2=CC(NC(=O)C)=CC=C21 CEJJPMISDMYGKE-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 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
- Patented Oct. 10, 1950 PRODUCTION OF PHENAZONIUM DYESTUFF IMAGES Vsevolod Tulagin, Phillipsburg, N. a, and Willy A. Schmidt, Easton, Pa, assignors to General Aniline & Film Corporation, New York, N. Y., a
- the present invention relates to the production of blue to reddish-blue phenazonium dyestuff images by color development of an exposed silver halide emulsion with an orthophenylenediamine type developer in the presence of a color former which is a B-naphthol derivative.
- magenta As a matter of fact, it may be said that these are the only shades Which areobtainable from phenols or naphthols when the coupling reaction takes place para to the phenolic hydroxyl group. This limitation on the shades of the dyestuffs produced according to the method of said application imposes a restriction on its use in three-color photography.
- Z is an alkyl radical as above or halogen, i. e., chlorine, bromine, or the like, a sulfonic acid group, or hydrogen.
- the color formers may be employed either in the emulsion or in the developer. However, where they contain a group preventing diffusion, in which case they are preferably used in the emulsion. Examples of compounds falling within such category are those in which the nitrogen atom is substituted by an aliphatic radical containing at least locarbon atoms, i. e., stearyl, and the like i
- the color developers which are employed are, as stated, of the ortho-phenylenediamine type, anumber of examples of which are referred to in the aforesaid Schmidt and Tulagin application.. Suitable developers of this class are; 7
- the invention may be effectuated so as to use the color developing method for producing colored negatives, colored positives, or reverse images.
- These general methods are conventional in the art, being dependent for their efficacy upon the point at which color development takes place.
- Example 1 A photographic silver bromide emulsion is exposed and color developed in the following developer:
- Example 2 The developer is the same as in Example 1 excepting that there is used 'l-acetamido-2- naphthol in lieu of the 'l-amino-2-naphthol.
- Example 3 A silver halide emulsion is exposed, developed in a black and white M-Q developer, re-exposed, and developed in a developer of the following composition:
- Example 4 4-;6"-dianilino .metanilic' acid. grams Sodium sulfite do 60 Potassium carbonate do.. .40 Pyridine cubic centimeters 12 Water do 1000 The film is then washed, bleached and fixed the conventional manner to yield a blue phenazonium dyestuif image.
- R is a member selected from the class consisting of'hydrogen, alkyl and aromatic radicals
- R1 is selected from the class consisting of hydrogen and acylamino
- Z is a member selected from the class consisting of hydrogen, halogen, alkyl and sulfo groups Z being in the ring 'fused to that containing the phenolic hydroxyl group.
- R is a member selected from the class consisting of hydrogen, alkyl and aromatic radicals
- R1 is selected from the class'consisting of hydrogen and acylamino
- Z is a member selected from the class consisting of h'ydrogen, halogen, alkyl and sulfo groups .Z'Sblllgill the ring fused to that containing the phenolic hydroxyl group.
- a photographic developer containing an ortho-phenylenediamine compound and as a color former capable of yielding'bluish phenazonium dyestuif images a compound of the following formula 5 6 wherein R is a member selected from the class oped with an ortho-phenylenediamine type deconsisting of hydrogen, alkyl and aromatic radiveloper 7-stearoylamino-2-naphthol.
- R1 is selected from the class consisting of hydrogen and acylamino
- Z is a member selected from the class consisting of hydrogen, 5 halogen, alkyl and sulfo groups Z being in the ring fused to that containing the phenolic hy- REFERENCES CITED .droxyl gr up, S Compound being e from The following references are of record in the groups rendering said compound non-diffusing in m f this patent; photographic emulsions. 10
- a photographic developer capable of yield- UNITED STATES PATENTS ing bluish phenazonium dyestuff images compris- Number Name Date ing 4.6-dianilino metanilic acid and 'I-amino-Z- 2,356,475 Schinzel Aug. 22, 1944 naphthol. 2,394,527 Woodward Feb. 5, 1945 7.
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Patented Oct. 10, 1950 PRODUCTION OF PHENAZONIUM DYESTUFF IMAGES Vsevolod Tulagin, Phillipsburg, N. a, and Willy A. Schmidt, Easton, Pa, assignors to General Aniline & Film Corporation, New York, N. Y., a
corporation of Delaware No Drawing. Application December 23, 1947, Serial No. 793,535
8 Claims.
The present invention relates to the production of blue to reddish-blue phenazonium dyestuff images by color development of an exposed silver halide emulsion with an orthophenylenediamine type developer in the presence of a color former which is a B-naphthol derivative.
Our copending application Serial Number 640,382, filed January 10, 1946, now Patent No. 2,486,440, of which the present application is a continuation in part describes the production of phenazonium dyestufi images by color developing an exposed silver halide emulsion with a color developer comprising an ortho-phenylenediamine type developer in the presence of various color formers. Among the color formers mentioned are those containing a phenolic hydroxyl group which couples in para. position to such group. It has been observed that with such color formers, the most common color of the dyestuff images obtained is either red or that shade of red known in the photographic artas.
magenta. As a matter of fact, it may be said that these are the only shades Which areobtainable from phenols or naphthols when the coupling reaction takes place para to the phenolic hydroxyl group. This limitation on the shades of the dyestuffs produced according to the method of said application imposes a restriction on its use in three-color photography.
It has now been discovered that phenazonium dyestufi images having a bluish shade, i. e., a
shade ranging from blue to reddish-blue are obtained by color developing an exposed silver halide emulsion with an ortho-phenylenediamine type developer in the presence of a fl-naphthol containing an amino Qrsubstituted amino group. 2 i The production of phenazonium dyestuif images by the utilization of such color formers and silver halide emulsions and color developers containing such color formers constitutes the purposes and objects of the present invention.
The ,B-naphthol compounds contemplated for employment herein may be represented by the following structural formula:
sulfonyl, and the like, and Z is an alkyl radical as above or halogen, i. e., chlorine, bromine, or the like, a sulfonic acid group, or hydrogen.
Examples of compounds embraced by this formula and which we have found to be eminently suitable in yielding the desirable blue images by color development with an orthophenylenediamine type developer are the following:
. 7-amino-2-naphthol.
. 7 -acetamido-2-naphthol.
. 7-benzoylamido-2-naphthol.
. 7-benzene sulfonylamido-2-naphthol. 7-methanesulfonylamino-2-naphthol. 7-anilino-2-naphthol.
. 7 -anisidino-2-naphthol.
. S-amino-Z-naphthol.
. B-acetamido-Z-naphthol.
10. 8-N-benzyl-benzoylamido-2-naphthol. ll. 5-acetamido-2-naphthol.
12. 3-anilino-2-naphthol.
13. 7-ethylamino-2-naphthol.
S-stearoyl sulfonylamido-2-naphthol. 8-amino-2-naphthol5sulfonic acid. 5-amino-2-naphthol-7-sulfonic acid. .17. 5-chloro-8amino-2-naphthol.
'18. 7-stearoylamido-2-naphthol.
These compounds are, for'the most part, known in the literature, and in any casecan be made by simple and well known chemical reactions, such as amidation, alkylation, halogenation, and the like. A description of the method of preparing the compounds is accordingly deemed to be unnecessary.
The color formers may be employed either in the emulsion or in the developer. However, where they contain a group preventing diffusion, in which case they are preferably used in the emulsion. Examples of compounds falling within such category are those in which the nitrogen atom is substituted by an aliphatic radical containing at least locarbon atoms, i. e., stearyl, and the like i The color developers which are employed are, as stated, of the ortho-phenylenediamine type, anumber of examples of which are referred to in the aforesaid Schmidt and Tulagin application.. Suitable developers of this class are; 7
4i-6-dia1iilino metanilic acid 4.6 bis (p methoxy phenylamino) met anilic acid 4 (o methoxy phenylamino) 6 (pmethoxy-phenylamino) metanilic acid I 4.6-bis-(o-methoxy phenylamino) metanilic acid 4 (p sulfo phenylamino) 6 dimethylamino metanilic acid, and the like.
The invention may be effectuated so as to use the color developing method for producing colored negatives, colored positives, or reverse images. These general methods are conventional in the art, being dependent for their efficacy upon the point at which color development takes place.
The invention is further illustrated by the following examples, but it is to be understood that the invention is not restricted thereto.
Example 1 A photographic silver bromide emulsion is exposed and color developed in the following developer:
4.6-dianilino metanilic acid grams 1.5 Sodium sulfite (anhydrous) do 60 Potassium carbonate (anhydrous) do 40 Pyridine cubic centimeters 12 7-amino-2-naphthol grams 1 Water cubic centimeters 1000 After development the film is washed for 15 minutes, the silver removed by the conventional ferricyanide bleach, and then fixed and washed. There is thus obtained a brilliant blue phenazonium dyestuff image.
Example 2 The developer is the same as in Example 1 excepting that there is used 'l-acetamido-2- naphthol in lieu of the 'l-amino-2-naphthol.
By processing the exposed silver halide emulsion as in Example 1 a blue phenazonium dyestufif image is obtained.
Example 3 A silver halide emulsion is exposed, developed in a black and white M-Q developer, re-exposed, and developed in a developer of the following composition:
4.6-dianilino metanilic acid grams Sodium sulfite (anhydrous) do 60 Potassium carbonate (anhydrous) do 40 Pyridine cubic centimeters 12 'l benzoylamido-2-naphthol grams 1 Water cubic centimeterse- 1000 The film is washed for 15 minutes, the silver bleached with a'ferricyanide bleach, fixed and washed. A blue phenazonium dyestufl image is thereby produced.
Example 4 4-;6"-dianilino .metanilic' acid. grams Sodium sulfite do 60 Potassium carbonate do.. .40 Pyridine cubic centimeters 12 Water do 1000 The film is then washed, bleached and fixed the conventional manner to yield a blue phenazonium dyestuif image.
The following table lists the color of the phenazonium dyestufi' images obtained when employing the developer of Example 4 with other color forming components of the fi-naphthol class here involved:
Table .1
Color of Formed Coupler Dye 7-benzenesulionylamido-2-napthol Bluish violet. 7-auilino-2-naphthol B 7-anisidino-2-naphth0l Do. S-amino-Z-naphthol. Do. S-acetamido-Z-naphthol. Do. S-N-benzyl-benzoylamido-2-napl1tho Do. S-acetamido-Z-napht Do. 3-anilino-2-naphthol Do.
Various modifications of the invention will occur to persons skilled in the art, and we therefore do not intend to be limited in the patent granted except as necessitated by the prior art wherein R is a member selected from the class consisting of'hydrogen, alkyl and aromatic radicals, R1 is selected from the class consisting of hydrogen and acylamino, and Z is a member selected from the class consisting of hydrogen, halogen, alkyl and sulfo groups Z being in the ring 'fused to that containing the phenolic hydroxyl group.
2 The process as defined in claim 1 wherein the color former is 'l-amino-Z-naphthol.
3. The process as defined in claim 1 wherein the color former is 'l-benzoylamido-Z-naphthol.
4. A photographic silver halide emulsion containing as a color former capable of yielding bluish phenazonium dyestuff images when color developed with an ortho-phenylenediamine type developer a compound of .the followin formula:
wherein R is a member selected from the class consisting of hydrogen, alkyl and aromatic radicals, R1 is selected from the class'consisting of hydrogen and acylamino, and Z is a member selected from the class consisting of h'ydrogen, halogen, alkyl and sulfo groups .Z'Sblllgill the ring fused to that containing the phenolic hydroxyl group.
5. A photographic developer containing an ortho-phenylenediamine compound and as a color former capable of yielding'bluish phenazonium dyestuif images a compound of the following formula 5 6 wherein R is a member selected from the class oped with an ortho-phenylenediamine type deconsisting of hydrogen, alkyl and aromatic radiveloper 7-stearoylamino-2-naphthol. cals, R1 is selected from the class consisting of hydrogen and acylamino, and Z isa member selected from the class consisting of hydrogen, 5 halogen, alkyl and sulfo groups Z being in the ring fused to that containing the phenolic hy- REFERENCES CITED .droxyl gr up, S Compound being e from The following references are of record in the groups rendering said compound non-diffusing in m f this patent; photographic emulsions. 10
6. A photographic developer capable of yield- UNITED STATES PATENTS ing bluish phenazonium dyestuff images compris- Number Name Date ing 4.6-dianilino metanilic acid and 'I-amino-Z- 2,356,475 Schinzel Aug. 22, 1944 naphthol. 2,394,527 Woodward Feb. 5, 1945 7. A photographic developer capable of yielding 15 2,441,491 Kendall et a1. May 11, 1948 bluish phenazonium dyestufl images comprising 2,445,252 Tulagin July 13, 1948 4.6-dianilino metanilic acid and 7-benzoylamido- 2 naphtho1 FOREIGN PATENTS 8. A photographic silver halide emulsion con- Number Country Date taining as a, color former capable of yielding bluish 531,312 Great Britain Jan. 1, 1941 phenazonium dyestutf images when color devel- 536,939 Great Britain June 3, 1941
Claims (1)
1. THE PROCESS OF PRODUCING BLUISH PHENAZONIUM DYESTUFF IMAGES BY COLOR FORMING DEVELOPMENT WHICH COMPRISES EXPOSING A SILVER HALIDE EMULSION AND DEVELOPING THE SAME WITH AN ORTHOPHENYLENEDIAMINE TYPE DEVELOPER IN THE PRESENCE OF A COLOR FORMER HAVING THE FOLLOWING FORMULA:
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US640382A US2486440A (en) | 1946-01-10 | 1946-01-10 | Production of phenazonium dyestuff images |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2525503A true US2525503A (en) | 1950-10-10 |
Family
ID=41210569
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US640382A Expired - Lifetime US2486440A (en) | 1946-01-10 | 1946-01-10 | Production of phenazonium dyestuff images |
| US793534A Expired - Lifetime US2525502A (en) | 1946-01-10 | 1947-12-23 | Production of phenazonium dyestuff images |
| US793533A Expired - Lifetime US2524741A (en) | 1946-01-10 | 1947-12-23 | Magenta phenazonium dyestuff images from 6-substituted-8-hydroxyquinoline couplers |
| US793536A Expired - Lifetime US2524725A (en) | 1946-01-10 | 1947-12-23 | Magenta phenazonium dyestuff images from 8-hydroxyquinoline couplers |
| US793535A Expired - Lifetime US2525503A (en) | 1946-01-10 | 1947-12-23 | Production of phenazonium dyestuff images |
| US101913A Expired - Lifetime US2570116A (en) | 1946-01-10 | 1949-06-28 | Color developers for the production of azine dye images |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US640382A Expired - Lifetime US2486440A (en) | 1946-01-10 | 1946-01-10 | Production of phenazonium dyestuff images |
| US793534A Expired - Lifetime US2525502A (en) | 1946-01-10 | 1947-12-23 | Production of phenazonium dyestuff images |
| US793533A Expired - Lifetime US2524741A (en) | 1946-01-10 | 1947-12-23 | Magenta phenazonium dyestuff images from 6-substituted-8-hydroxyquinoline couplers |
| US793536A Expired - Lifetime US2524725A (en) | 1946-01-10 | 1947-12-23 | Magenta phenazonium dyestuff images from 8-hydroxyquinoline couplers |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US101913A Expired - Lifetime US2570116A (en) | 1946-01-10 | 1949-06-28 | Color developers for the production of azine dye images |
Country Status (6)
| Country | Link |
|---|---|
| US (6) | US2486440A (en) |
| BE (6) | BE470459A (en) |
| CH (5) | CH280516A (en) |
| DE (6) | DE851163C (en) |
| FR (6) | FR939497A (en) |
| GB (5) | GB644863A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1041356B (en) * | 1955-11-18 | 1958-10-16 | Gen Aniline & Film Corp | Photographic silver halide emulsion for color development |
| US2921851A (en) * | 1958-04-03 | 1960-01-19 | Gen Aniline & Film Corp | Production of yellow dye images by color development |
| US3174862A (en) * | 1959-09-11 | 1965-03-23 | Agfa Ag | Process for improving the color reproduction in color photographic material |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2611785A (en) * | 1952-09-23 | N-substituted x | ||
| CH277023A (en) * | 1949-05-03 | 1951-08-15 | Ciba Geigy | Process for the production of an intermediate product. |
| US2575027A (en) * | 1949-10-29 | 1951-11-13 | Gen Aniline & Film Corp | N-substituted 4, 6-diamino metanilic acids |
| US2596926A (en) * | 1949-12-16 | 1952-05-13 | Gen Aniline & Film Corp | Preparation of azine dye images |
| US2594917A (en) * | 1949-12-16 | 1952-04-29 | Gen Aniline & Film Corp | Suppression of proximity development with azine color developers |
| US2623823A (en) * | 1950-03-21 | 1952-12-30 | Gen Aniline & Film Corp | Energizers for aromatic triamino developing agents and suppression of proximity development in azine color developers |
| US2618559A (en) * | 1950-03-21 | 1952-11-18 | Gen Aniline & Film Corp | Stain preventing shortstop bath for photographic azine dye images |
| US2687431A (en) * | 1950-12-20 | 1954-08-24 | Gen Aniline & Film Corp | Process of preparing nitro phenylenediamines |
| BE508676A (en) * | 1951-01-26 | |||
| US2691588A (en) * | 1952-03-14 | 1954-10-12 | Eastman Kodak Co | Photographic developers containing 8-hydroxyquinolines |
| US2701766A (en) * | 1952-06-14 | 1955-02-08 | Gen Aniline & Film Corp | Developers for and method of producing phenazonium dyestuff images with p-dialkylaminoaniline developing agents |
| BE526742A (en) * | 1953-02-24 | |||
| US2945761A (en) * | 1957-07-29 | 1960-07-19 | Eastman Kodak Co | Reactivity of couplers incorporated in photographic emulsions |
| US3099559A (en) * | 1959-08-31 | 1963-07-30 | Gen Aniline & Film Corp | Silver-free color reproduction process and composition therefor |
| US3050394A (en) * | 1959-09-30 | 1962-08-21 | Gen Aniline & Film Corp | Method of incorporating color couplers in hydrophlic colloids |
| US3077403A (en) * | 1960-05-31 | 1963-02-12 | Gen Aniline & Film Corp | Color former containing bis coupling functions |
| US4511569A (en) * | 1982-08-26 | 1985-04-16 | Schering Corporation | Tricyclic lactams and derivatives useful in increasing cardiac contractility |
| JPS59177554A (en) * | 1983-03-28 | 1984-10-08 | Fuji Photo Film Co Ltd | Silver halide color photosensitive material |
| SE8302361D0 (en) * | 1983-04-27 | 1983-04-27 | Astra Laekemedel Ab | NEW TRICYCLIC AMINES |
| US4680299A (en) * | 1984-04-30 | 1987-07-14 | E.I. Du Pont De Nemours And Company | 2-phenyl-4-quinolinecarboxylic acids and pharmaceutical compositions thereof |
| US4847381A (en) * | 1987-08-31 | 1989-07-11 | American Cyanamid Company | 2-Phenyl-4-quinoline carboxylic acids |
| US5260177A (en) * | 1988-03-16 | 1993-11-09 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| US5223386A (en) * | 1989-03-04 | 1993-06-29 | Konica Corporation | Cyan coupler |
| EP0386931A1 (en) * | 1989-03-04 | 1990-09-12 | Konica Corporation | A novel cyan coupler |
| US4990436A (en) * | 1990-01-23 | 1991-02-05 | Eastman Kodak Company | Cyan dye-forming couplers and photographic recording materials containing same |
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| GB531312A (en) * | 1939-03-31 | 1941-01-01 | Eastman Kodak Co | Improvements in and relating to colour forming developers and processes of colour development |
| GB536939A (en) * | 1939-08-24 | 1941-06-03 | Eastman Kodak Co | Improvements in and relating to photographic colour development |
| US2356475A (en) * | 1936-07-07 | 1944-08-22 | Eastman Kodak Co | Phenolic and naphtholic couplers containing sulphonamide groups |
| US2394527A (en) * | 1942-11-04 | 1946-02-05 | Du Pont | Color photography |
| US2441491A (en) * | 1944-05-12 | 1948-05-11 | Ilford Ltd | Cyanacetylamino phenol color formers for color photography |
| US2445252A (en) * | 1947-04-10 | 1948-07-13 | Gen Aniline & Film Corp | Photographic elements containing urethanes of nu-substituted j acids as color formers |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB178986A (en) * | 1921-02-11 | 1922-05-04 | John Augustus Ward | Improvements in and relating to advertising apparatus |
| US1782356A (en) * | 1927-11-14 | 1930-11-18 | Firm J R Geigy S A | Manufacture of acid dyestuffs of the phenonaphthosafranine series |
| US1886809A (en) * | 1929-09-04 | 1932-11-08 | Gen Aniline Works Inc | Arylated safranines and process of preparing them |
| BE369421A (en) * | 1929-09-09 | |||
| GB458664A (en) * | 1935-03-21 | 1936-12-21 | Eastman Kodak Co | Improvements in and relating to colour forming developers and processes of colour development |
| DE767652C (en) * | 1936-05-27 | 1953-03-02 | Ig Farbenindustrie Ag | Process for the color development of halogen silver emulsions |
| US2306410A (en) * | 1936-07-07 | 1942-12-29 | Eastman Kodak Co | Color development |
| US2196739A (en) * | 1938-09-23 | 1940-04-09 | Eastman Kodak Co | Photographic developer for color photography |
| US2193015A (en) * | 1939-05-24 | 1940-03-12 | Eastman Kodak Co | Developer containing sulphonamide groups |
| BE442586A (en) * | 1940-07-31 | |||
| FR956696A (en) * | 1941-08-08 | 1950-02-02 | ||
| FR956698A (en) * | 1941-09-11 | 1950-02-02 | ||
| GB553064A (en) * | 1941-09-25 | 1943-05-06 | Eastman Kodak Co | Improvements in photographic developers |
| US2364350A (en) * | 1941-11-06 | 1944-12-05 | Eastman Kodak Co | Photographic developer |
| US2400872A (en) * | 1942-09-01 | 1946-05-28 | Eastman Kodak Co | Diamino-nu-alkyl phenazinium salts |
| BE465025A (en) * | 1945-01-27 | |||
| US2489440A (en) * | 1945-05-03 | 1949-11-29 | Naylor Brothers Ltd | Conveyer |
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1946
- 1946-01-10 US US640382A patent/US2486440A/en not_active Expired - Lifetime
- 1946-12-11 GB GB36617/46A patent/GB644863A/en not_active Expired
-
1947
- 1947-01-03 FR FR939497D patent/FR939497A/en not_active Expired
- 1947-01-10 BE BE470459D patent/BE470459A/xx unknown
- 1947-12-23 US US793534A patent/US2525502A/en not_active Expired - Lifetime
- 1947-12-23 US US793533A patent/US2524741A/en not_active Expired - Lifetime
- 1947-12-23 US US793536A patent/US2524725A/en not_active Expired - Lifetime
- 1947-12-23 US US793535A patent/US2525503A/en not_active Expired - Lifetime
-
1948
- 1948-12-10 FR FR61005D patent/FR61005E/en not_active Expired
- 1948-12-10 FR FR61007D patent/FR61007E/en not_active Expired
- 1948-12-10 FR FR61004D patent/FR61004E/en not_active Expired
- 1948-12-10 FR FR61006D patent/FR61006E/en not_active Expired
- 1948-12-10 FR FR58855D patent/FR58855E/en not_active Expired
- 1948-12-14 GB GB32321/48A patent/GB647638A/en not_active Expired
- 1948-12-14 DE DEP24686D patent/DE851163C/en not_active Expired
- 1948-12-14 DE DEP24684D patent/DE854889C/en not_active Expired
- 1948-12-14 GB GB32322/48A patent/GB646490A/en not_active Expired
- 1948-12-14 DE DEP24685D patent/DE817554C/en not_active Expired
- 1948-12-14 GB GB32257/48A patent/GB646348A/en not_active Expired
- 1948-12-14 GB GB32258/48A patent/GB649811A/en not_active Expired
- 1948-12-14 DE DEP24683A patent/DE850385C/en not_active Expired
- 1948-12-14 DE DEP24682A patent/DE837959C/en not_active Expired
- 1948-12-20 CH CH280516D patent/CH280516A/en unknown
- 1948-12-21 BE BE486430D patent/BE486430A/xx unknown
- 1948-12-21 BE BE486433D patent/BE486433A/xx unknown
- 1948-12-21 BE BE486434D patent/BE486434A/xx unknown
- 1948-12-22 CH CH280517D patent/CH280517A/en unknown
- 1948-12-22 CH CH283788D patent/CH283788A/en unknown
- 1948-12-22 CH CH280518D patent/CH280518A/en unknown
- 1948-12-22 CH CH283787D patent/CH283787A/en unknown
-
1949
- 1949-01-01 DE DEP29268A patent/DE848155C/en not_active Expired
- 1949-01-15 BE BE486432D patent/BE486432A/xx unknown
- 1949-01-15 BE BE486431D patent/BE486431A/xx unknown
- 1949-06-28 US US101913A patent/US2570116A/en not_active Expired - Lifetime
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| US2356475A (en) * | 1936-07-07 | 1944-08-22 | Eastman Kodak Co | Phenolic and naphtholic couplers containing sulphonamide groups |
| GB531312A (en) * | 1939-03-31 | 1941-01-01 | Eastman Kodak Co | Improvements in and relating to colour forming developers and processes of colour development |
| GB536939A (en) * | 1939-08-24 | 1941-06-03 | Eastman Kodak Co | Improvements in and relating to photographic colour development |
| US2394527A (en) * | 1942-11-04 | 1946-02-05 | Du Pont | Color photography |
| US2441491A (en) * | 1944-05-12 | 1948-05-11 | Ilford Ltd | Cyanacetylamino phenol color formers for color photography |
| US2445252A (en) * | 1947-04-10 | 1948-07-13 | Gen Aniline & Film Corp | Photographic elements containing urethanes of nu-substituted j acids as color formers |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1041356B (en) * | 1955-11-18 | 1958-10-16 | Gen Aniline & Film Corp | Photographic silver halide emulsion for color development |
| US2921851A (en) * | 1958-04-03 | 1960-01-19 | Gen Aniline & Film Corp | Production of yellow dye images by color development |
| US3174862A (en) * | 1959-09-11 | 1965-03-23 | Agfa Ag | Process for improving the color reproduction in color photographic material |
Also Published As
| Publication number | Publication date |
|---|---|
| US2486440A (en) | 1949-11-01 |
| BE486432A (en) | 1949-01-15 |
| US2524741A (en) | 1950-10-03 |
| CH280518A (en) | 1952-01-31 |
| CH280517A (en) | 1952-01-31 |
| CH283787A (en) | 1952-06-30 |
| US2524725A (en) | 1950-10-03 |
| GB646490A (en) | 1950-11-22 |
| BE486434A (en) | 1949-01-15 |
| FR58855E (en) | 1954-04-06 |
| DE851163C (en) | 1952-10-02 |
| DE817554C (en) | 1951-10-18 |
| DE850385C (en) | 1952-09-25 |
| CH283788A (en) | 1952-06-30 |
| DE854889C (en) | 1952-11-06 |
| US2525502A (en) | 1950-10-10 |
| CH280516A (en) | 1952-01-31 |
| GB644863A (en) | 1950-10-18 |
| FR61005E (en) | 1955-03-23 |
| FR939497A (en) | 1948-11-16 |
| GB646348A (en) | 1950-11-22 |
| BE486431A (en) | 1948-12-21 |
| GB649811A (en) | 1951-01-31 |
| BE486433A (en) | 1949-01-15 |
| GB647638A (en) | 1950-12-20 |
| DE848155C (en) | 1952-11-04 |
| BE486430A (en) | 1949-01-16 |
| FR61007E (en) | 1955-03-23 |
| DE837959C (en) | 1952-05-05 |
| BE470459A (en) | 1947-02-28 |
| FR61006E (en) | 1955-03-23 |
| US2570116A (en) | 1951-10-02 |
| FR61004E (en) | 1955-03-23 |
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