US2487569A - Antistain baths for color photographic materials - Google Patents
Antistain baths for color photographic materials Download PDFInfo
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- US2487569A US2487569A US40010A US4001048A US2487569A US 2487569 A US2487569 A US 2487569A US 40010 A US40010 A US 40010A US 4001048 A US4001048 A US 4001048A US 2487569 A US2487569 A US 2487569A
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- color
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- water
- baths
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- 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
- G03C7/3046—Processing baths not provided for elsewhere, e.g. final or intermediate washings
Definitions
- This inv n io relates to ph to a ic e sta n ba hs, to .antiestain 'ba hs mp oyed in mu ti lay r color p to raphy, a d esp c l y final rinse baths for the washing of multi-layer colo p oto aph c material .o in th fixin trea me t-s a to pr ent t iorma ion 0i stai I s vknown tha in he rocessing o mul color reversible an mum-colo re ersible White op qu the ex osed mm r exnosedr h te opaque, is first developed with a normal black and white developer to produce a negative image.
- the black and white negative material After development, the black and white negative material, without being fixed, is exposed to general illumination, followed by a second development with a color forming developer. Duringthe first and second development, the silver-halides in all the layers are reduced to metallic silver. After the s c nd develo n he m i is cleared in running'water, hardened in an aqueous solution consisting of either alum or potassium c om a um andt n as in unning water- Aiter the latter treatment, the silver present all the layers formed during the first and second d elo men is co v ted i a sa by and 9f the known silver-salt formers, as bleaching baths, and the silver-salt $11311 iormedis then removed by dissolvingitin a silver-.- salt solvent such as, for example, hypo. The material is then washed for .a long period of timeand then dried.
- a silver-.- salt solvent such as,
- a iii-1 K 53? obj ct at th in ent n is finalrinee bath which clears undesirable matter from a multi-color photographic material in a short time while avoiding staining.
- alkyl i. e., methyl, ethyl, propyl, isopropyl, butyl, etc.
- alkylene i. e., l-butenyl, etc aryl, i. e., phenyl, naphthyl, etc., and aralkyl, -i. e., benzyl, methylbenzyl, ethylbenzyl, etc.
- 'InFormula 2 Z represents hydrogen, amino, alkyl, 1. e., methyl, ethyl,'-butyl, etc., p'henyl, phenylenahydroxy, alkox-y, i.
- alkylthio alkyl-S-
- X is hydrogen or a primary amino and I hydrazino, "phenyl, hydroxy, alkoxy, i. e., butoxy, etc,, or an alkylthio (alkyl-S-i group, i. e., methylthio, ethylthio, propylthio, etc.
- the water-soluble addition products of formaldehyde and an azine characterized by Formula 1 are prepared according to the methods described in United States Patent 2,197,357.
- the water-soluble products while utilizing the azines of Formulae 2 and 3 are prepared according to the methods described in United States Patents, 2,211,? 10 and 2,211,709, respectively.
- the concentration of the addition products required may vary from as little as 0.5%, an amount which in general has been found to eliminate stain for the most part, to as much as 5%, an amount which is an assurance that stain formation will not ensue. Amounts higher than 5% give little improvement. Concentrations ranging from between 2 and 4% are most desirable from a commercial standpoint.
- the photographic multi-layer materials which may be processed with the anti-stain bath of the present invention, are color reversible film, color negative film, color reversible white printing material coated on an opaque base, and color positive printing material coated on paper, irrespective of whether the dyestuff images are produced with color formers present in the emulsion, or by a selective second exposure followed by development with developing solutions containing color formers and color developing agents.
- the color reversible film consists of an integral tripack emulsion coated on the usual clear cellulose acetate or nitrate film base. Each of the emulsion are sensitized to one of the primary colors of light, namely, blue, green, and red.
- the top layer is blue sensitive.
- a filter layer, yellow in color and blue absorbing, lies under the top layer. Below this filter layer, lies a green sensitive emulsion layer, and below this is a red sensitive emulsion layer.
- Each of the three silver-halide emulsion layers contain dye-forming compounds which unite during the development of a silver image in an aromatic amine developing agent to form a dye with the oxidation product of the developing agent, or may be free from color formers in which case the film is processed with the color formers in the color developers by the selective second exposure and color development method as described in United States Patents 1,897,866, 1,900,870, 1,928,709 and 1,980,941.
- a yellow dye is formed in the blue sensitive emulsion; a magenta dye is formed in the green sensitive emulsion; and a cyan dye is formed in the red sensitive emulsion. Combinations of these 4 three printing primaries will produce all of the other colors in the finished film or print.
- the color negative film is made up in the same: manner as the color reversible film with the ex-- ception that it may contain a layer of clear" gelatin between the red sensitive layer and the green sensitive layer.
- the color reversible white opaque material is prepared in the same manner as color reversible film and the color negative film with the exception that the base consists of an opaque white film.
- the color paper is also constructed in the same manner as the color reversible film and the color negative film, with the exception that the emulsion is coated on a baryta coated paper base. Suitable methods for the preparation of photographic multi--layer materials have been described in the literature relating to color photography and are, therefore, not described here.
- Example I A 4" x 5" full color transparency sheet of color.” film was printed by contact on two 4" x 5" sheets of color reversible white opaque film.
- the film was washed for two minutes in running water 68 F. and re-exposed to white light.
- the re-exposed film was color developed for fifteen minutes at 68 F. in a developer of the following composition:
- Example II Example III Example I was repeated with the exception that the colored material employed was a color transparency sheet and the final rinse bath consisted of 97 parts by weight of water and 3 parts by weight of a water-soluble addition product of formaldehyde and melamine, trimethylolmelamine, prepared according to Example VI of United States Patent 2,197,357. After fixing and washing, the color print washed in water showed objectionable stains, while the color print treated with the aqueous solution containing the addition product was clear and unstained.
- the colored material employed was a color transparency sheet and the final rinse bath consisted of 97 parts by weight of water and 3 parts by weight of a water-soluble addition product of formaldehyde and melamine, trimethylolmelamine, prepared according to Example VI of United States Patent 2,197,357.
- Example IV Example IV was repeated with the exception that the final rinse consisted of 98 parts by weight of water and 2 parts by weight of trimethylolmelamine available commercially under the brand name of "I a-rial: MR1! and having the fol-lowing formula:
- the treated and untreated prints of Examples 11 to IV inclusive were stored for several months.
- the untreated prints showed marked staining during storage and the color balance after storage was completely ruined by yellow stains, whereas no stains were evident on the treated prints and the color balance was unafiected.
- water-soluble addition products of formaldehyde and an azine in aqueous solutions as a final rinse bath, they may be incorporated into gelatin solutions in a concentration ranging from 25% and such gelatin solutions utilized as a surface coating for the processed multi-layer photographic material.
- At least one Y is an amino group having at least one reactive hydrogen atom, the remaining Ys being a radical selected from the group consisting of hydrogen, hydroxyl, halogen, alkyl, alkylene, aryl and aralkyl
- Z represents a member selected from the group consisting of hydrogen amino, hydroxy, alkyl, alkoxy, phenyl, phenylene, mercapto, alkylthio and hydrazino, at least two Zs being a member selected from the class consisting of amino and hydrazino group
- X represents a member selected from the groupconsisting of hydrogen and a primary amino group
- R represents a member of the group consisting of halogen, hydroxy, hydrazino, alkoxy, phenyl, and alkylthio groups.
Description
Patented Nov. 8, 1949 UNITED STAT ES.
,ANTISTAIN BATHS Eon copoa .PHQIOGBABHIO MATERIALS S udderMe key, B cn '& Film Corporation,
to General Aniline N. Y., assignor NewYork,
N. "Y., a -eorporation of Delaware No Drawing. Applicationluly 21, 1948, SeriaL .0; 0
4 Claims. 1
This inv n io relates to ph to a ic e sta n ba hs, to .antiestain 'ba hs mp oyed in mu ti lay r color p to raphy, a d esp c l y final rinse baths for the washing of multi-layer colo p oto aph c material .o in th fixin trea me t-s a to pr ent t iorma ion 0i stai I s vknown tha in he rocessing o mul color reversible an mum-colo re ersible White op qu the ex osed mm r exnosedr h te opaque, is first developed with a normal black and white developer to produce a negative image. After development, the black and white negative material, without being fixed, is exposed to general illumination, followed by a second development with a color forming developer. Duringthe first and second development, the silver-halides in all the layers are reduced to metallic silver. After the s c nd develo n he m i is cleared in running'water, hardened in an aqueous solution consisting of either alum or potassium c om a um andt n as in unning water- Aiter the latter treatment, the silver present all the layers formed during the first and second d elo men is co v ted i a sa by and 9f the known silver-salt formers, as bleaching baths, and the silver-salt $11311 iormedis then removed by dissolvingitin a silver-.- salt solvent such as, for example, hypo. The material is then washed for .a long period of timeand then dried.
common y lsnown triazines contemplated for reaction with the formaldehyde have'the following formulae:
In'Formula l at least one Y is an amino group having at least one reactive hydrogen atom, the
remaining 'Ys being a radical such as hydrogen,
' amino, hydroxy, halogen, i. e., chlorine, bromine,
During the final washing operation 'itis essential that the residual second or :oolor developer and bleach solutions be removed, otherwise stains will be formed during the drying operation, which are particularly noticeable in the white area. In
order to prevent this staining, an extended final washing time in running water of irom fifteen minutes to two hours has been proposed. Even if this proposal be adopted, stains arenevertheless. formed during and after the drying operation. It is believed that the staining results from the oxidation of'traces ofthe color developer retained in the layers of the material following color-forming eve o ment, w ich hen. rea t w th he amused colo imme An b e t of th present inve t on s t eii ni nate excessive washing time of color developed inulti eetlorp otographic ma r a whi e p eve ngthe intimatio i tain.
. A iii-1 K 53? obj ct at th in ent n is finalrinee bath which clears undesirable matter from a multi-color photographic material in a short time while avoiding staining.
Other objects and features of the invention ,Will become apparent as the description proceeds. I I have discovered that the above .pb'iects are accomplished lay-employing as a final rinsebat-h -an aqueous solution containing a small quantity of a water-soluble addition product :of formalde' h de a diazine riaz ne. The an T1. represents halogen,
methoxy, ethoxy, propoxy, I
etc., alkyl, i. e., methyl, ethyl, propyl, isopropyl, butyl, etc., alkylene, i. e., l-butenyl, etc aryl, i. e., phenyl, naphthyl, etc., and aralkyl, -i. e., benzyl, methylbenzyl, ethylbenzyl, etc. 'InFormula 2 Z represents hydrogen, amino, alkyl, 1. e., methyl, ethyl,'-butyl, etc., p'henyl, phenylenahydroxy, alkox-y, i. e., methoxy, ethoxy, propoxy, etc., mereapto, alkylthio (alkyl-S-), i. e., methylthio, ethylthio, propylthio, etc., and hydrazino, at least two Zs being primary amino or hydrazino. In Formula 3 X is hydrogen or a primary amino and I hydrazino, "phenyl, hydroxy, alkoxy, i. e., butoxy, etc,, or an alkylthio (alkyl-S-i group, i. e., methylthio, ethylthio, propylthio, etc.
The water-soluble addition products of formaldehyde and an azine characterized by Formula 1 are prepared according to the methods described in United States Patent 2,197,357. The water-soluble products while utilizing the azines of Formulae 2 and 3 are prepared according to the methods described in United States Patents, 2,211,? 10 and 2,211,709, respectively.
'By utilizing this final rinse bath, in lieu of extended washi in wate the washin time a e "fixing is considerably reduced, and stain formation prevented, The exact operation of the water-soluble addition products of formaldehyde and an azine in the final rinse bath is unknown and to date has been unascertainable. it is known that the tendency to stain formation encountered in the processing of color film by the co lggprforming development method is attributable 3 in the main to the retention in the layers of the multi-layer material of small amount of the color developer. This becomes progressively oxidized by atmospheric conditions, the oxidized products reacting with unused and unremoved color former.
It is likewise known that this tendency to stain formation can be obviated by the utilization of reducing agents such as alkali sulfite, hydrazines, hydroxylamines and the like which operate to destroy the retained color developer. Rather peculiarly, it has been found that the addition products referred to hereinabove are analogous to the reducing agents to the extent that both overcome the tendency to stain formation. Despite the factv that the addition products would not appear to be constituted in a fashion to permit them to act as reducin agents, it would, nevertheless, appear that they may have this property because of the results they achieve. In any case, the conclusion is inescapable that the addition products either function as reducing agents to destroy the color developer, or react With the color developer or the oxidation products thereof in a manner to prevent subsequent reaction of the color developer with retained color former.
The concentration of the addition products required may vary from as little as 0.5%, an amount which in general has been found to eliminate stain for the most part, to as much as 5%, an amount which is an assurance that stain formation will not ensue. Amounts higher than 5% give little improvement. Concentrations ranging from between 2 and 4% are most desirable from a commercial standpoint.
The photographic multi-layer materials, which may be processed with the anti-stain bath of the present invention, are color reversible film, color negative film, color reversible white printing material coated on an opaque base, and color positive printing material coated on paper, irrespective of whether the dyestuff images are produced with color formers present in the emulsion, or by a selective second exposure followed by development with developing solutions containing color formers and color developing agents.
The color reversible film consists of an integral tripack emulsion coated on the usual clear cellulose acetate or nitrate film base. Each of the emulsion are sensitized to one of the primary colors of light, namely, blue, green, and red. The top layer is blue sensitive. A filter layer, yellow in color and blue absorbing, lies under the top layer. Below this filter layer, lies a green sensitive emulsion layer, and below this is a red sensitive emulsion layer. Each of the three silver-halide emulsion layers contain dye-forming compounds which unite during the development of a silver image in an aromatic amine developing agent to form a dye with the oxidation product of the developing agent, or may be free from color formers in which case the film is processed with the color formers in the color developers by the selective second exposure and color development method as described in United States Patents 1,897,866, 1,900,870, 1,928,709 and 1,980,941.
As silver is formed during development, it must be removed after color development by treatment in a bleach, followed by treatment in a bath of sodium thiosulfate, according to usual practice. A yellow dye is formed in the blue sensitive emulsion; a magenta dye is formed in the green sensitive emulsion; and a cyan dye is formed in the red sensitive emulsion. Combinations of these 4 three printing primaries will produce all of the other colors in the finished film or print.
The color negative film is made up in the same: manner as the color reversible film with the ex-- ception that it may contain a layer of clear" gelatin between the red sensitive layer and the green sensitive layer. The color reversible white opaque material is prepared in the same manner as color reversible film and the color negative film with the exception that the base consists of an opaque white film. The color paper is also constructed in the same manner as the color reversible film and the color negative film, with the exception that the emulsion is coated on a baryta coated paper base. Suitable methods for the preparation of photographic multi--layer materials have been described in the literature relating to color photography and are, therefore, not described here.
The following examples describe in detail. methods for accomplishing the above objects, but it is to be understood that. they are inserted merely for purposes of illustration and are not to be construed as limiting the scope of the invention.
Example I A 4" x 5" full color transparency sheet of color." film was printed by contact on two 4" x 5" sheets of color reversible white opaque film.
The two sheets of 4" x 5" color reversible white opaque film were first developed for twelve minutes at 68 F. in a developer of the following composition:
p-Monomethylaminephenol sulfate grams 3 Sodium sulfite do 50 Hydroquinone do 6 Sodium carbonate (monohydrate) do 40 Sodium thiocyanate do 2 Potassium bromide do 2 Water to make liter 1 The developed film was short stopped for three minutes at 68 F. in a 5% aqueous solution of sodium bisulfite.
The film was washed for two minutes in running water 68 F. and re-exposed to white light.
The re-exposed film was color developed for fifteen minutes at 68 F. in a developer of the following composition:
p-Aminodiethylaniline HCl grams 4 Sodium sulfite do 20 Hydroxylamine HCl do 2, Sodium carbonate do Potassium bromiden do 1 Water to make liter 1 Di-potassium mono-sodium ferricyanide grams Potassium bromide do 15 Disodium phosphate do 40 Sodium bisulfate do 25 Formalin (40%)s cubic centimeters" 20 Water to make liter 1 'The bleached film was washed for five minaromas utes at 68 F., and then fixed forfive minutes in a solution of the following composition:
Hypo grams 200 Borax do Water to make l-iter 1 water-soluble addition product of "formaldehyde methylol-cyanurtrihyand cyanurtrihydrazide, drazide, prepared according to Example I of United States Patent 2,211,709, and then allowed to dry. At this point, the prints appeared identical. After normal drying, the print'rinsed in the solution containing the addition product of formaldehyde and cyanurtrihydrazide showed brighter colors and more brilliant highlights. The print given only a water washing for five to twenty minutes showed a slight highlight stain.
When the drying was carried out under conditions of high humidity so that the drying time was extended for several hours, the water-rinsed print showed even greater highlight stains While the print rinsed in the aqueous solution containing the addition product did not change.
After storing both prints, 1. e., treated and untreated for several months, it was observed that the color balance of the treated print was unaffected, whereas the color balance of the untreated print was completely ruined by yellow stain appearing overall, while at the same time the densities of the original yellow image were lowered.
Example II Example III Example I was repeated with the exception that the colored material employed was a color transparency sheet and the final rinse bath consisted of 97 parts by weight of water and 3 parts by weight of a water-soluble addition product of formaldehyde and melamine, trimethylolmelamine, prepared according to Example VI of United States Patent 2,197,357. After fixing and washing, the color print washed in water showed objectionable stains, while the color print treated with the aqueous solution containing the addition product was clear and unstained.
Example IV Example I was repeated with the exception that the final rinse consisted of 98 parts by weight of water and 2 parts by weight of trimethylolmelamine available commercially under the brand name of "I a-rial: MR1! and having the fol-lowing formula:
omen The color print washed inwater showed objectionable stains after drying, while the print treated with the solution containing the-trimethylolmelamine was clear and unstained.
Similar results were obtained as in the preceding examples when the addition products of Examples .2,- 4, and "5 of United States Patent 2,211,709, Examples 3, 4, and 16 of United States Patent 2,211,710, and Examples 4, 7, and 15 of United States Patent 2,197,357 were employed.
The treated and untreated prints of Examples 11 to IV inclusive were stored for several months. The untreated prints showed marked staining during storage and the color balance after storage was completely ruined by yellow stains, whereas no stains were evident on the treated prints and the color balance was unafiected.
Instead of employing the water-soluble addition products of formaldehyde and an azine in aqueous solutions as a final rinse bath, they may be incorporated into gelatin solutions in a concentration ranging from 25% and such gelatin solutions utilized as a surface coating for the processed multi-layer photographic material.
The above specific examples are to be regarded as being merely illustrative of the invention and not in any sense restrictive. It will be obvious to those skilled in the art that many modifications, such as substituting equivalent materials and varying the proportions of the materials used,
may be made. The scope of the invention is to be limited solely by the appended claims.
I claim:
1. In a process of producing color photographic images in a silver-halide emulsion by exposing the emulsion, color-forming developing the same, bleaching, fixing, and washing, the improvement which comprises avoiding the formation of stain, after the bleaching and washing operation, by rinsing the said silver-halide emulsion with an aqueous solution containing a water-soluble addition product of formaldehyde and an azine selected from the class consisting of those having the following formulae:
wherein at least one Y is an amino group having at least one reactive hydrogen atom, the remaining Ys being a radical selected from the group consisting of hydrogen, hydroxyl, halogen, alkyl, alkylene, aryl and aralkyl, Z represents a member selected from the group consisting of hydrogen amino, hydroxy, alkyl, alkoxy, phenyl, phenylene, mercapto, alkylthio and hydrazino, at least two Zs being a member selected from the class consisting of amino and hydrazino group,
X represents a member selected from the groupconsisting of hydrogen and a primary amino group, R represents a member of the group consisting of halogen, hydroxy, hydrazino, alkoxy, phenyl, and alkylthio groups.
2. In a process of producing color photographic images in a silver-halide emulsion by exposing the emulsion, color-forming developing the same, bleaching, fixing, and washing, the improvement which comprises avoiding the formation of stain, after the bleaching and washing operation, by rinsing the said silver-halide emulsion with an aqueous solution containing methylolcyanurtrihydrazide.
3. In a process of producing color photographic images in a silver-halide emulsion by exposing the emulsion, color-forming developing the same,
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,384,658 Vittum Sept. 11, 1945 2.440.954 Jennings May 4, 1948
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE490235D BE490235A (en) | 1948-07-21 | ||
| US40010A US2487569A (en) | 1948-07-21 | 1948-07-21 | Antistain baths for color photographic materials |
| GB14278/49A GB659362A (en) | 1948-07-21 | 1949-05-27 | Anti-stain baths for color photographic materials |
| FR990966D FR990966A (en) | 1948-07-21 | 1949-07-19 | Improvements in the production of color photographic images |
| CH291226D CH291226A (en) | 1948-07-21 | 1949-07-21 | A method of preventing the formation of spots in color photography. |
| DEP49482A DE857738C (en) | 1948-07-21 | 1949-07-21 | Process for preventing staining on color images |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40010A US2487569A (en) | 1948-07-21 | 1948-07-21 | Antistain baths for color photographic materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2487569A true US2487569A (en) | 1949-11-08 |
Family
ID=21908578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US40010A Expired - Lifetime US2487569A (en) | 1948-07-21 | 1948-07-21 | Antistain baths for color photographic materials |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2487569A (en) |
| BE (1) | BE490235A (en) |
| CH (1) | CH291226A (en) |
| DE (1) | DE857738C (en) |
| FR (1) | FR990966A (en) |
| GB (1) | GB659362A (en) |
Cited By (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2629660A (en) * | 1950-12-01 | 1953-02-24 | Gen Aniline & Film Corp | Antifading baths for photographic black-and-white prints |
| US2647057A (en) * | 1950-10-31 | 1953-07-28 | Pavelle Color Inc | Protecting color pictures exposed to high humidities against fading and staining |
| DE960517C (en) * | 1950-07-12 | 1957-03-21 | Agfa Ag Fuer Photogabrikation | Process for producing durable subtractive color photographic images |
| US2976207A (en) * | 1959-02-27 | 1961-03-21 | Standard Oil Co | Dihydroxy-aminotriazine insecticides |
| US2980678A (en) * | 1958-01-06 | 1961-04-18 | Ici Ltd | Pyrimidines |
| US2983611A (en) * | 1957-09-16 | 1961-05-09 | Eastman Kodak Co | Gelatin compositions containing hardeners |
| US2994637A (en) * | 1957-11-13 | 1961-08-01 | Diamond Alkali Co | Aminopyrimidines as fungicides |
| US3053656A (en) * | 1954-07-01 | 1962-09-11 | Polaroid Corp | Photographic silver halide developers containing triazine rings |
| US3083097A (en) * | 1957-04-26 | 1963-03-26 | Agfa Ag | Bleaching silver images in the formation of printing plates |
| US3249603A (en) * | 1960-08-09 | 1966-05-03 | Hoffmann La Roche | Novel pyrimidine sulfanilamides and processes for their preparation |
| US3325287A (en) * | 1963-11-26 | 1967-06-13 | Fuji Photo Film Co Ltd | Photographic gelatin hardening composition |
| US3391019A (en) * | 1964-02-21 | 1968-07-02 | Ici Ltd | Process for coating shaped hydrophobic polymeric materials with reaction product of halogenotriazine and polymer containing hydroxyl, amino or mercapto group |
| US3429878A (en) * | 1967-01-31 | 1969-02-25 | Smithkline Corp | 6-amino-5-methyleneaminopyrimidines |
| US3461461A (en) * | 1965-11-01 | 1969-08-12 | Upjohn Co | 6-amino-4-(substituted amino)-1,2-dihydro-1-hydroxy-2-iminopyrimidines |
| US3464987A (en) * | 1966-02-21 | 1969-09-02 | Upjohn Co | 1,2-dihydro-1-hydroxy-2-imino-6-(lower alkyl)pyrimidines |
| US3473929A (en) * | 1965-09-09 | 1969-10-21 | Eastman Kodak Co | Method of inhibiting discoloration of color photographs |
| US4046503A (en) * | 1975-04-12 | 1977-09-06 | Henkel & Cie Gmbh | Developer-coupler hair dyes based on alkoxy-triamino-pyrimidines |
| US4150228A (en) * | 1976-05-14 | 1979-04-17 | Polaroid Corporation | Thioether substituted silver halide solvents |
| US4255574A (en) * | 1973-02-26 | 1981-03-10 | Hoffmann-La Roche Inc. | Process for preparing 2,4-diamino-pyrimidines |
| US4336254A (en) * | 1981-03-24 | 1982-06-22 | Smithkline Corporation | Guanidinopyrimidine compounds, compositions and method of using as a diuretic |
| US4336255A (en) * | 1981-03-24 | 1982-06-22 | Smithkline Corporation | Pharmaceutical compositions containing guanidinopyrimidines |
| EP0127162A2 (en) * | 1983-05-25 | 1984-12-05 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material |
| US4786583A (en) * | 1987-06-22 | 1988-11-22 | Eastman Kodak Company | Stabilizing bath for use in photographic processing |
| US4797352A (en) * | 1984-06-08 | 1989-01-10 | Konishiroku Photo Industry Co., Ltd. | Method of processing a silver halide photographic light-sensitive material |
| US5217852A (en) * | 1990-12-07 | 1993-06-08 | Fuji Photo Film Co., Ltd. | Color image-stabilization processing solution used for processing a silver halide color photographic material and a processing method using the same |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE563764A (en) * | 1957-01-10 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2384658A (en) * | 1943-07-10 | 1945-09-11 | Eastman Kodak Co | Color photography |
| US2440954A (en) * | 1945-08-23 | 1948-05-04 | Du Pont | Process for eliminating stain from color-yielding elements by treatment with aromatic aldehydes containing an acyl group |
-
0
- BE BE490235D patent/BE490235A/xx unknown
-
1948
- 1948-07-21 US US40010A patent/US2487569A/en not_active Expired - Lifetime
-
1949
- 1949-05-27 GB GB14278/49A patent/GB659362A/en not_active Expired
- 1949-07-19 FR FR990966D patent/FR990966A/en not_active Expired
- 1949-07-21 DE DEP49482A patent/DE857738C/en not_active Expired
- 1949-07-21 CH CH291226D patent/CH291226A/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2384658A (en) * | 1943-07-10 | 1945-09-11 | Eastman Kodak Co | Color photography |
| US2440954A (en) * | 1945-08-23 | 1948-05-04 | Du Pont | Process for eliminating stain from color-yielding elements by treatment with aromatic aldehydes containing an acyl group |
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE960517C (en) * | 1950-07-12 | 1957-03-21 | Agfa Ag Fuer Photogabrikation | Process for producing durable subtractive color photographic images |
| US2647057A (en) * | 1950-10-31 | 1953-07-28 | Pavelle Color Inc | Protecting color pictures exposed to high humidities against fading and staining |
| US2629660A (en) * | 1950-12-01 | 1953-02-24 | Gen Aniline & Film Corp | Antifading baths for photographic black-and-white prints |
| US3053656A (en) * | 1954-07-01 | 1962-09-11 | Polaroid Corp | Photographic silver halide developers containing triazine rings |
| US3083097A (en) * | 1957-04-26 | 1963-03-26 | Agfa Ag | Bleaching silver images in the formation of printing plates |
| US2983611A (en) * | 1957-09-16 | 1961-05-09 | Eastman Kodak Co | Gelatin compositions containing hardeners |
| US2994637A (en) * | 1957-11-13 | 1961-08-01 | Diamond Alkali Co | Aminopyrimidines as fungicides |
| US2980678A (en) * | 1958-01-06 | 1961-04-18 | Ici Ltd | Pyrimidines |
| US2976207A (en) * | 1959-02-27 | 1961-03-21 | Standard Oil Co | Dihydroxy-aminotriazine insecticides |
| US3249603A (en) * | 1960-08-09 | 1966-05-03 | Hoffmann La Roche | Novel pyrimidine sulfanilamides and processes for their preparation |
| US3325287A (en) * | 1963-11-26 | 1967-06-13 | Fuji Photo Film Co Ltd | Photographic gelatin hardening composition |
| US3391019A (en) * | 1964-02-21 | 1968-07-02 | Ici Ltd | Process for coating shaped hydrophobic polymeric materials with reaction product of halogenotriazine and polymer containing hydroxyl, amino or mercapto group |
| US3473929A (en) * | 1965-09-09 | 1969-10-21 | Eastman Kodak Co | Method of inhibiting discoloration of color photographs |
| US3461461A (en) * | 1965-11-01 | 1969-08-12 | Upjohn Co | 6-amino-4-(substituted amino)-1,2-dihydro-1-hydroxy-2-iminopyrimidines |
| US3464987A (en) * | 1966-02-21 | 1969-09-02 | Upjohn Co | 1,2-dihydro-1-hydroxy-2-imino-6-(lower alkyl)pyrimidines |
| US3429878A (en) * | 1967-01-31 | 1969-02-25 | Smithkline Corp | 6-amino-5-methyleneaminopyrimidines |
| US4255574A (en) * | 1973-02-26 | 1981-03-10 | Hoffmann-La Roche Inc. | Process for preparing 2,4-diamino-pyrimidines |
| US4046503A (en) * | 1975-04-12 | 1977-09-06 | Henkel & Cie Gmbh | Developer-coupler hair dyes based on alkoxy-triamino-pyrimidines |
| US4150228A (en) * | 1976-05-14 | 1979-04-17 | Polaroid Corporation | Thioether substituted silver halide solvents |
| US4336254A (en) * | 1981-03-24 | 1982-06-22 | Smithkline Corporation | Guanidinopyrimidine compounds, compositions and method of using as a diuretic |
| US4336255A (en) * | 1981-03-24 | 1982-06-22 | Smithkline Corporation | Pharmaceutical compositions containing guanidinopyrimidines |
| EP0127162A2 (en) * | 1983-05-25 | 1984-12-05 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material |
| US4555479A (en) * | 1983-05-25 | 1985-11-26 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material |
| EP0127162A3 (en) * | 1983-05-25 | 1987-02-25 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material |
| US4797352A (en) * | 1984-06-08 | 1989-01-10 | Konishiroku Photo Industry Co., Ltd. | Method of processing a silver halide photographic light-sensitive material |
| US4786583A (en) * | 1987-06-22 | 1988-11-22 | Eastman Kodak Company | Stabilizing bath for use in photographic processing |
| US5217852A (en) * | 1990-12-07 | 1993-06-08 | Fuji Photo Film Co., Ltd. | Color image-stabilization processing solution used for processing a silver halide color photographic material and a processing method using the same |
| US5348845A (en) * | 1990-12-07 | 1994-09-20 | Fuji Photo Film Co., Ltd. | Color image-stabilization processing solution used for processing a silver halide color photographic material and a processing method using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE857738C (en) | 1952-12-01 |
| BE490235A (en) | |
| CH291226A (en) | 1953-06-15 |
| FR990966A (en) | 1951-09-28 |
| GB659362A (en) | 1951-10-24 |
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