US2949360A - Photographic color former dispersions - Google Patents
Photographic color former dispersions Download PDFInfo
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- US2949360A US2949360A US607257A US60725756A US2949360A US 2949360 A US2949360 A US 2949360A US 607257 A US607257 A US 607257A US 60725756 A US60725756 A US 60725756A US 2949360 A US2949360 A US 2949360A
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- solvent
- water
- color
- parts
- coupler
- Prior art date
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- 239000006185 dispersion Substances 0.000 title claims description 26
- 239000002904 solvent Substances 0.000 claims description 68
- 108010010803 Gelatin Proteins 0.000 claims description 26
- 229920000159 gelatin Polymers 0.000 claims description 26
- 239000008273 gelatin Substances 0.000 claims description 26
- 235000019322 gelatine Nutrition 0.000 claims description 26
- 235000011852 gelatine desserts Nutrition 0.000 claims description 26
- 239000000839 emulsion Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 229910052709 silver Inorganic materials 0.000 claims description 16
- 239000004332 silver Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- -1 AMINO Chemical class 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 3
- 229940011051 isopropyl acetate Drugs 0.000 claims description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229960001413 acetanilide Drugs 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 229940124543 ultraviolet light absorber Drugs 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- AYLDJQABCMPYEN-UHFFFAOYSA-N (4-azaniumylphenyl)-diethylazanium;sulfate Chemical compound OS(O)(=O)=O.CCN(CC)C1=CC=C(N)C=C1 AYLDJQABCMPYEN-UHFFFAOYSA-N 0.000 description 1
- NABFRHBCIHEYTA-UHFFFAOYSA-N 2,5-bis(6-methylheptyl)benzene-1,4-diol Chemical compound CC(C)CCCCCC1=CC(O)=C(CCCCCC(C)C)C=C1O NABFRHBCIHEYTA-UHFFFAOYSA-N 0.000 description 1
- ZZXILYOBAFPJNS-UHFFFAOYSA-N 2-octylbenzene-1,4-diol Chemical compound CCCCCCCCC1=CC(O)=CC=C1O ZZXILYOBAFPJNS-UHFFFAOYSA-N 0.000 description 1
- NFOQRIXSEYVCJP-UHFFFAOYSA-N 2-propoxycarbonylbenzoic acid Chemical compound CCCOC(=O)C1=CC=CC=C1C(O)=O NFOQRIXSEYVCJP-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- JANBFCARANRIKJ-UHFFFAOYSA-N bis(3-methylbutyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCOC(=O)C1=CC=CC=C1C(=O)OCCC(C)C JANBFCARANRIKJ-UHFFFAOYSA-N 0.000 description 1
- DMNQTEVDCGAATA-UHFFFAOYSA-N bis(oxolan-2-ylmethyl) hexanedioate Chemical compound C1CCOC1COC(=O)CCCCC(=O)OCC1CCCO1 DMNQTEVDCGAATA-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- ZWDZJRRQSXLOQR-UHFFFAOYSA-N n-butyl-n-phenylacetamide Chemical compound CCCCN(C(C)=O)C1=CC=CC=C1 ZWDZJRRQSXLOQR-UHFFFAOYSA-N 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N para-methylaniline Natural products CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- JQMQIRDMGUZAOM-UHFFFAOYSA-N tris(4-butylphenyl) phosphate Chemical compound C1=CC(CCCC)=CC=C1OP(=O)(OC=1C=CC(CCCC)=CC=1)OC1=CC=C(CCCC)C=C1 JQMQIRDMGUZAOM-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 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
- G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
- G03C7/3885—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific solvent
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
United States Patent O PHOTOGRAPHIC COLOR FORD [ER DISPERSIONS Donald B. Julian, Rochester, N.Y., assignor to Eastman Kodak Company, Rochester, N.Y., a corporation of New Jersey No Drawing. Filed Aug. 31, 1956, Ser. No. 607,257
3 Claims. (Cl. 96-97) This invention relates to color photography and particularly to a method for incorporating couplers in silver halide emulsion layers.
Color-forming compounds of the water-insoluble type which are capable of coupling with the oxidation product of primary aromatic amino developing agents are usually incorporated in silver halide emulsions by first dissolving them in an organic solvent, dispersing this solution in aqueous gelatin and mixing the resulting dispersion with the silver halide emulsion. Processes of this type are described in Jelley and Vittum U.S. Patent 2,322,027 and Fierke and Chechak U.S. Patent 2,801,- 171. The Fierke and Chechak patent describes a process whereby the ratio of coupler solvent to coupler may be considerably reduced so that the final coating does not contain a large amount of organic solvent.
One of the diiiiculties encountered in these methods of incorporating the coupler in the emulsion is the tendency of the coupler to crystallize in the emulsion. When the auxiliary solvent has appreciable water-solubility, some of this solvent dissolves in the gelatin solution during the disperson operation, and this may take place so rapidly that there is insufiicient solvent in the coupler phase to keep the coupler in solution. Some of the coupler then crystallizes. This crystallization of the coupler is undesirable because the coupler reacts less solvent and an auxiliary solvent, or which may be one or more auxiliary solvents alone.
The regular solvent is a high boiling, organic, crystalloidal coupler solvent, substantially water-insoluble, of low molecular weight, having a boiling point above about 175 C. at atmospheric pressure, having a high solvent action :for the coupler and for dyes formed therefrom, and being permeable to photographic developer oxidation products. Coupler solvents of this class include (1) alkyl esters of phthalic acid in which the alkyl radical preferably contains less than 6 carbon atoms, e.g., methyl phthalate, ethyl phthalate, propyl phthalate, n-butyl phthalate, di-n-ebutyl phthalate, n-amyl phthalate, isoamyl phthalate and dioctyl phthalate, (2) esters of phosphoric acid, e.g., triphenyl phosphate, tricresyl phosphate and diphenyl mono-p-tert. butyl phenyl phosphate, and (3) alkyl amides \or acetanilide, e.g., -N,n-butylacetanilide and Nmethyl-p1methyl acetanilide. The regular coupler solvent should have a water solubility of less than about 0.1 part of solvent in 100 parts of water, and is generally used in an amount less than one part of coupler solvent per part of coupler by Weight.
The auxiliary solvents with which the present invention is useful should have a Water solubility Within the range of about 2.5 to 100 parts of solvent in 100 parts of water. If the water solubility of the solvent is less than about 2.5 parts of solvent in 100 parts of water, the loss of solvent to the aqueous gelatin solution becomes too small to be important. If the water solubility of the solvent is greater than about 100 parts of solvent in 100 parts of water, it is difiicult to saturate the gelatin solution with the solvent and thereby to prevent loss of solvent to the gelatin solution from the coupler dispersion. Suitable auixilary solvents include esters of aliphatic alcohols with acetic or propionic acid, e.g., ethyl acetate,
isopropyl acetate, ethyl propionate, fi-ethoxyethyl acetate,
readily in the color-forming reaction when crystalline and therefore yields less dye.
It is therefore an object of the present invention to provide a novel method for incorporating color couplers in photographic emulsions. A further object is to provide a method for decreasing the tendency of the coupler to crystallize when incorporated in the emulsion. Other objects will appear from the following description of my invention.
These objects are accomplished by dissolving the coupler in a solvent which may include both a -regular solvent and an auxiliary solvent, or which may include one or more auxiliary solvents without the regular solvent, dispersing the solution in gelatin to which auxiliary solvent has been added, chilling and setting the gelatin dispersion, removing substantially all of the auxiliary solvent from the dispersion by washing or drying, and mixing the dispersion with a gelatino-silver halide emul- SlOIl.
Couplers which may be used according to my invention are those disclosed in Jelley and Vittum U.S. Patent 2,322,027 and Fierke and Chechak U.S. Patent 2,801,171. More specifically I may employ Z-(a-di-tertamylphenoxy-n-butyrylamino)-4,6-dichloro-5-methylphenol as a cyan-forming coupler, 1-(2',4',6'-trichlorophenyl)-3-[3"- (2"',4-di-tert.amylphenoxyacetamido) benzamidol-S- pyrazolone as a magenta-forming coupler and N-(4benzoylacetaminobenzenesulfonyl) N (y-phenylpropyD- p-toluidine as a yellow-forming coupler.
According to my process the coupler is first dissolved in an organic solvent which is a mixture of a regular and fi butoxy-fi-ethoxyethyl acetate. Typical solvents of this class together with their boiling points and water solubilities are as follows:
After dissolving the coupler in the coupler solvent or mixture of coupler solvents, the solution is dispersed in a solution of gelatin. Prior to adding the coupler solution to the gelatin, there is added to the gelatin solution enough auxiliary solvent to saturate the gelatin solution. The coupler solution is dispersed in the gelatin by passing the mixture through a colloid mill or homogenizer and the coupler dispersion in gelatin is then chilled and set. The gelatin dispersion is then noodled, washed and dried. if an auxiliary solvent of appreciable Water-solubility has been employed, Washing removes substantially all of this solvent; or if a low-boiling solvent has been used, drying removes most of this solvent and at least of the Water. The dispersion may be kept in this form for an appreciable time and when it is to be used it is rernelted, or if previously dried, redispersed in Water, and mixed with the gelatino-silver halide emulsion in the usual manner. If a high-boiling regular solvent has been employed, it is retained in the coupler dispersion and is then incorporated in the final silver halide emulsion. It is usually desirable to have some regular solvent in the final coating.
A suitable ratio of coupler to regular coupler solvent would be 40 grams of coupler to 20 grams of regular solvent or a ratio of 1: /z. The following example contains di-n-butyl phthalate as the regular solvent and B-ethoxyethyl acetate as the auxiliary solvent, although other mixtures and ratios may obviously be employed.
Example Forty grams of the coupler, Z-(u-di-tert. amylphenoxyn-butyrylamino)-4,6-dichloro--methyl phenol, were dissolved in a solution of 20 grams of di-n-butyl phthalate and 60 grams of fl-ethoxy ethyl acetate at 280 F. A gelatin solution was prepared containing 272 grams of gelatin solution in water, 40 cc. of 7 /2 Alkanol B solution and 80 grams of fi-ethoxyethyl acetate, dissolved at 120 F. The coupler solution was poured into the gelatin solution, stirred for about one minute and passed through a colloid mill five times. The dispersion was set up on a chill plate at 40 F., noodled and Washed for 6 hours in cool water to remove the auxiliary solvent. After remelting, the coupler dispersion was incorporated in a gelatino-silver halide emulsion. Eight grams of the coupler dispersion was added to a gelatino-silver halide emulsion containing approximately 0.046 mole of silver halide, and after coating on a film support the emulsion was exposed and processed in a developer of the following composition to produce a cyan image.
Grams p-Amino diethylaniline sulfate 2 Sodium sulfite, anhydrous 5 Sodium carbonate, anhydrous Potassium bromide 2 Benzyl alcohol 10 Water to 1 liter.
Compounds other than couplers such as antistain agents and ultraviolet light absorbers may be dispersed in gelatin by my method. Suitable antistain agents which can be incorporated in this way are 2,5-di-iso-octyl hydroquinone and 2,5-di-n octyl hydroquinone. A suitable ultraviolet light absorber which can be incorporated by my method is o-methosulfobenzyl-3-phenyl-2-phenylamido-4-thiazolidone.
It will be understood that my invention is to be taken as limited only by the scope of the appended claims.
What I claim is:
1. The method of incorporating a color coupler in a gelatino-silver halide emulsion, which comprises dissolving a waterdnsoluble color-forming compound capable of reacting with a primary aromatic amino developing agent on photographic development to form a dye, in a solvent including (a) at least an auxiliary solvent having a solubility of at least 2.5 parts of solvent in parts of water and not more than 100 parts of solvent in 100 parts of water, said auxiliary solvent being selected from the group consisting of ethyl acetate, isopropyl acetate, ethyl-propionate, fi-ethoxyethyl acetate, fl-butoxyethyl B-ethoxyethyl acetate, methyl-n-propyl ketone and di(tetrahydrofurfuryl) adipate and (b) less than about one part per part of color-forming compound of a substantially water-insoluble, low molecular weight, organic crystalloidal solvent for the color-forming compound, said crystalloidal solvent having a boiling point above about C. and a solubility of less than about 0.1;part of solvent in 100 parts of water and having a high solvent action for the color-forming compound and for dyes formed therefrom, and being permeable to photographic developer oxidation products, dispersing the solution in aqueous gelatin previously approximately saturated with at least one of said auxiliary solvents, chilling and setting the gelatin dispersion, removing substantially all of said auxiliary solvent from the dispersion and mixing the dispersion with a gelatino-silver halide emulsion.
2. The method of incorporating a color coupler in a gelatino-silver halide emulsion, which comprises dissolving a water-insoluble color-forming compound capable of reacting with a primary aromatic amino developing agent on photographic development to form a dye, in a solvent mixture of di-n-butyl phthalate and fi-ethoxyethyl acetate, dispersing the solution in aqueous gelatin previously approximately saturated with B-ethoxyethyl ace- 'tate, chilling and setting the gelatin dispersion, removing substantially all of said fi-ethoxyethyl acetate from the dispersion and mixing the dispersion with a gelatinosilver halide emulsion.
3. The method of incorporating a color coupler in a -gelatino-silver halide emulsion, which comprises dissolving Z-(oz-Cll-tfilt. amylphenoxy-n-butyrylamino)-4,6-dichloro-S-methyl phenol in a solvent mixture of di-n-butyl phthalate and ,B-ethoxyethyl acetate, dispersing the solution in aqueous gelatin previously approximately saturated with fi-ethoxyethyl acetate, chilling and setting the gelatin dispersion, removing substantially all of said [3- ethoxyethyl acetate from the dispersion and mixing the dispersion with a gelatino-silver halide emulsion.
References Cited in the file of this patent UNITED STATES PATENTS 2,322,027 Jelley et al. June 15, 1943 2,787,544 Godowsky et al. Apr. 2, 1957 I 2,801,171 Fierke et al. July 30, 1957
Claims (1)
1. THE METHOD OF INCORPORATING A COLOR COUPLER IN A GELATINO-SILVER HALIDE EMULSION, WHICH COMPRISES DISSOLVING A WATER-INSOLUBLE COLOR-FORMING COMPOUND CAPABLE OF REACTING WITH A PRIMARY AROMATIC AMINO DEVELOPING AGENT ON PHOTOGRAPHIC DEVELOPMENT TO FORM A DYE, IN A SOLVENT INCLUDING (A) AT LEAST AN AUXILIARY SOLVENT HAVING A SOLUBILITY OF AT LEAST 2.5 PARTS OF SOLVENT IN 100 PARTS OF WATER AND NOT MORE THAN 100 PARTS OF SOLVENT IN 100 PARTS OF WATER, SAID AUXILIARY SOLVENT BEING SELECTED FROM THE GROUP CONSISTING OF ETHYL ACETATE, ISOPROPYL ACETATE, ETHYL-PROPIONATE, B-ETHOXYETHYL ACETATE, B-BUTOXYETHYL B-ETHOXYETHYL ACETATE, METHYL-N-PROPYL KETONE AND DI-TETRAHYDROFURFURYL) ADIPATE AND (B) LESS THAN ABOUT ONE PART PER PART OF COLOR-FORMING COMPOUND OF A SUBSTANTIALLY WATER-INSOLUBLE, LOW MOLECULAR WEIGHT, ORGANIC CRYSTALLOIDAL SOLVENT FOR THE COLOR-FORMING COMPOUND, SAID CRYSTALLOIDAL SOLVENT HAVING A BOILING POINT ABOVE ABOUT 175*C. AND A SOLUBILITY OF LESS THAN ABOUT 0.1 PART OF SOLVENT IN 100 PARTS OF WATER AND HAVING A HIGH SOLVENT ACTION FOR THE COLOR-FORMING COMPOUND AND FOR DYES FORMED THEREFROM, AND VEING PERMEABLE TO PHOTOGRAPHIC DEVELOPER OXIDATION PRODUCTS, DISPERSING THE SOLUTION IN AQUEOUS GELATIN PREVIOUSLY APPROXIMATELY SATURATED WITH AT LEAST ONE OF SAID AUXILIARY SOLVENTS, CHILLING AND SETTING THE GELATIN DISPERSION, REMOVING SUBSTANTIALLY ALL OF SAID AUXILIARY SOLVENT FROM THE DISPERSION AND MIXING THE DISPERSION WITH A GELATINO-SILVER HALIDE EMULSION.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US607257A US2949360A (en) | 1956-08-31 | 1956-08-31 | Photographic color former dispersions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US607257A US2949360A (en) | 1956-08-31 | 1956-08-31 | Photographic color former dispersions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2949360A true US2949360A (en) | 1960-08-16 |
Family
ID=24431497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US607257A Expired - Lifetime US2949360A (en) | 1956-08-31 | 1956-08-31 | Photographic color former dispersions |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2949360A (en) |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3092495A (en) * | 1960-06-09 | 1963-06-04 | Gen Aniline & Film Corp | Lower alkyl lactate coupler solvents |
| US3255012A (en) * | 1960-08-20 | 1966-06-07 | Agfa Ag | Sensitized color photographic emulsions and processes containing color couplers |
| US3316094A (en) * | 1963-03-11 | 1967-04-25 | Gen Aniline & Film Corp | Method of incorporating color couplers in hydrophilic colloids |
| US3431107A (en) * | 1967-07-28 | 1969-03-04 | Eastman Kodak Co | Dye developer image transfer systems |
| US4066457A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Color developer for diffusion transfer |
| US4066456A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Incorporated carboxy substituted p-phenylenediamine color developer |
| US4233397A (en) * | 1976-12-08 | 1980-11-11 | Fuji Photo Film Co., Ltd. | Process for the preparation of coupler dispersions |
| US4278757A (en) * | 1978-08-10 | 1981-07-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive material |
| US4430421A (en) | 1982-01-26 | 1984-02-07 | Agfa-Gevaert, N.V. | Method of dispersing photographic adjuvants in hydrophilic colloid compositions |
| US4430422A (en) | 1982-01-26 | 1984-02-07 | Agfa-Gevaert, N.V. | Method of dispersing photographic adjuvants in a hydrophilic colloid composition |
| EP0124795A2 (en) | 1983-04-11 | 1984-11-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion |
| US4822724A (en) * | 1986-12-18 | 1989-04-18 | Minnesota Mining And Manufacturing Company | Process for the formation of stable color photographic images |
| EP0320939A2 (en) | 1987-12-15 | 1989-06-21 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US5008179A (en) * | 1989-11-22 | 1991-04-16 | Eastman Kodak Company | Increased activity precipitated photographic materials |
| US5045442A (en) * | 1990-09-27 | 1991-09-03 | Eastman Kodak Company | Photographic materials with novel cyan dye forming couplers |
| EP0452984A1 (en) | 1985-09-25 | 1991-10-23 | Fuji Photo Film Co., Ltd. | Process for processing silver halide color photographic material for photographing use |
| WO1991017480A1 (en) * | 1990-04-30 | 1991-11-14 | Eastman Kodak Company | Method of preparing coupler dispersions for photographic use |
| US5182190A (en) * | 1988-01-18 | 1993-01-26 | Eastman Kodak Company | Method for obtaining a photographic coating composition |
| WO1993003420A1 (en) * | 1991-07-29 | 1993-02-18 | Eastman Kodak Company | Method of preparing coupler dispersions |
| US5484695A (en) * | 1994-02-18 | 1996-01-16 | Eastman Kodak Company | Surfactants and hydrophilic colloid compositions and materials containing them |
| US5763150A (en) * | 1995-07-25 | 1998-06-09 | Eastman Kodak Company | Surfactants and hydrophilic colloid compositions and materials containing them |
| US6420103B1 (en) | 1999-03-10 | 2002-07-16 | Eastman Kodak Company | Photographic element |
| US6525115B2 (en) | 2000-12-05 | 2003-02-25 | Eastman Kodak Company | Method of making an aqueous dispersion of particles comprising an epoxy material for use in coatings |
| US20050089806A1 (en) * | 2003-10-24 | 2005-04-28 | Zengerle Paul L. | Method of preparation of direct dispersions of photographically useful chemicals |
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| US2787544A (en) * | 1954-12-20 | 1957-04-02 | Eastman Kodak Co | Method of making photographic packet emulsions |
| US2801171A (en) * | 1954-12-20 | 1957-07-30 | Eastman Kodak Co | Photographic color former dispersions |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US2322027A (en) * | 1940-02-24 | 1943-06-15 | Eastman Kodak Co | Color photography |
| US2787544A (en) * | 1954-12-20 | 1957-04-02 | Eastman Kodak Co | Method of making photographic packet emulsions |
| US2801171A (en) * | 1954-12-20 | 1957-07-30 | Eastman Kodak Co | Photographic color former dispersions |
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3092495A (en) * | 1960-06-09 | 1963-06-04 | Gen Aniline & Film Corp | Lower alkyl lactate coupler solvents |
| US3255012A (en) * | 1960-08-20 | 1966-06-07 | Agfa Ag | Sensitized color photographic emulsions and processes containing color couplers |
| US3316094A (en) * | 1963-03-11 | 1967-04-25 | Gen Aniline & Film Corp | Method of incorporating color couplers in hydrophilic colloids |
| US3431107A (en) * | 1967-07-28 | 1969-03-04 | Eastman Kodak Co | Dye developer image transfer systems |
| US4066457A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Color developer for diffusion transfer |
| US4066456A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Incorporated carboxy substituted p-phenylenediamine color developer |
| US4233397A (en) * | 1976-12-08 | 1980-11-11 | Fuji Photo Film Co., Ltd. | Process for the preparation of coupler dispersions |
| US4278757A (en) * | 1978-08-10 | 1981-07-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive material |
| US4430421A (en) | 1982-01-26 | 1984-02-07 | Agfa-Gevaert, N.V. | Method of dispersing photographic adjuvants in hydrophilic colloid compositions |
| US4430422A (en) | 1982-01-26 | 1984-02-07 | Agfa-Gevaert, N.V. | Method of dispersing photographic adjuvants in a hydrophilic colloid composition |
| EP0124795A2 (en) | 1983-04-11 | 1984-11-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion |
| EP0452984A1 (en) | 1985-09-25 | 1991-10-23 | Fuji Photo Film Co., Ltd. | Process for processing silver halide color photographic material for photographing use |
| US4822724A (en) * | 1986-12-18 | 1989-04-18 | Minnesota Mining And Manufacturing Company | Process for the formation of stable color photographic images |
| EP0320939A2 (en) | 1987-12-15 | 1989-06-21 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US5182190A (en) * | 1988-01-18 | 1993-01-26 | Eastman Kodak Company | Method for obtaining a photographic coating composition |
| US5008179A (en) * | 1989-11-22 | 1991-04-16 | Eastman Kodak Company | Increased activity precipitated photographic materials |
| WO1991017480A1 (en) * | 1990-04-30 | 1991-11-14 | Eastman Kodak Company | Method of preparing coupler dispersions for photographic use |
| US5045442A (en) * | 1990-09-27 | 1991-09-03 | Eastman Kodak Company | Photographic materials with novel cyan dye forming couplers |
| WO1993003420A1 (en) * | 1991-07-29 | 1993-02-18 | Eastman Kodak Company | Method of preparing coupler dispersions |
| US5380628A (en) * | 1991-07-29 | 1995-01-10 | Eastman Kodak Company | Method of preparing coupler dispersions |
| US5484695A (en) * | 1994-02-18 | 1996-01-16 | Eastman Kodak Company | Surfactants and hydrophilic colloid compositions and materials containing them |
| US5543555A (en) * | 1994-02-18 | 1996-08-06 | Eastman Kodak Company | Surfactants and hydrophilic colloid compositions and materials containing them |
| US5763150A (en) * | 1995-07-25 | 1998-06-09 | Eastman Kodak Company | Surfactants and hydrophilic colloid compositions and materials containing them |
| US5952521A (en) * | 1995-07-25 | 1999-09-14 | Eastman Kodak Company | Surfactants and hydrophilic colloid compositions and materials |
| US6420103B1 (en) | 1999-03-10 | 2002-07-16 | Eastman Kodak Company | Photographic element |
| US6525115B2 (en) | 2000-12-05 | 2003-02-25 | Eastman Kodak Company | Method of making an aqueous dispersion of particles comprising an epoxy material for use in coatings |
| US20050089806A1 (en) * | 2003-10-24 | 2005-04-28 | Zengerle Paul L. | Method of preparation of direct dispersions of photographically useful chemicals |
| US7338756B2 (en) | 2003-10-24 | 2008-03-04 | Eastman Kodak Company | Method of preparation of direct dispersions of photographically useful chemicals |
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