US2487569A - Antistain baths for color photographic materials - Google Patents
Antistain baths for color photographic materials Download PDFInfo
- Publication number
- 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
- Authority
- US
- United States
- Prior art keywords
- color
- film
- water
- baths
- silver
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000463 material Substances 0.000 title description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 26
- 239000000839 emulsion Substances 0.000 description 18
- -1 amino, hydroxy Chemical group 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000002441 reversible effect Effects 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 238000004061 bleaching Methods 0.000 description 5
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010981 drying operation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 2
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
- 241000256844 Apis mellifera Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 229910001864 baryta Inorganic materials 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910021538 borax Inorganic materials 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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 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
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Images
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
- G03C7/3046—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.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
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 (fr) | 1948-07-21 | 1949-07-19 | Perfectionnements aux procédés de production d'images photographiques en couleurs |
DEP49482A DE857738C (de) | 1948-07-21 | 1949-07-21 | Verfahren zur Verhinderung von Fleckenbildungen auf Farbbildern |
CH291226D CH291226A (fr) | 1948-07-21 | 1949-07-21 | Procédé pour empêcher, dans la photographie en couleurs, la formation de taches. |
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 (de) * | 1950-07-12 | 1957-03-21 | Agfa Ag Fuer Photogabrikation | Verfahren zur Herstellung haltbarer subtraktiver farbenphotographischer Bilder |
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 |
US4555479A (en) * | 1983-05-25 | 1985-11-26 | 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/fr not_active Expired
- 1949-07-21 DE DEP49482A patent/DE857738C/de not_active Expired
- 1949-07-21 CH CH291226D patent/CH291226A/fr unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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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 (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE960517C (de) * | 1950-07-12 | 1957-03-21 | Agfa Ag Fuer Photogabrikation | Verfahren zur Herstellung haltbarer subtraktiver farbenphotographischer Bilder |
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 |
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 |
---|---|
FR990966A (fr) | 1951-09-28 |
CH291226A (fr) | 1953-06-15 |
BE490235A (en)) | |
GB659362A (en) | 1951-10-24 |
DE857738C (de) | 1952-12-01 |
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