US2318788A - Incorporation of couplers in nongelatin emulsions - Google Patents
Incorporation of couplers in nongelatin emulsions Download PDFInfo
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- US2318788A US2318788A US363012A US36301240A US2318788A US 2318788 A US2318788 A US 2318788A US 363012 A US363012 A US 363012A US 36301240 A US36301240 A US 36301240A US 2318788 A US2318788 A US 2318788A
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- Prior art keywords
- gelatin
- emulsion
- coupler
- emulsions
- couplers
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- 239000000839 emulsion Substances 0.000 title description 45
- 238000010348 incorporation Methods 0.000 title description 3
- 229920000159 gelatin Polymers 0.000 description 32
- 239000008273 gelatin Substances 0.000 description 32
- 108010010803 Gelatin Proteins 0.000 description 30
- 235000019322 gelatine Nutrition 0.000 description 30
- 235000011852 gelatine desserts Nutrition 0.000 description 30
- -1 silver halide Chemical class 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 17
- 229910052709 silver Inorganic materials 0.000 description 17
- 239000004332 silver Substances 0.000 description 17
- 229920002678 cellulose Polymers 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 125000002252 acyl group Chemical group 0.000 description 7
- 239000001913 cellulose Substances 0.000 description 7
- 235000010980 cellulose Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229920002301 cellulose acetate Polymers 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000020 Nitrocellulose Substances 0.000 description 3
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920001220 nitrocellulos Polymers 0.000 description 3
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- 239000012780 transparent material Substances 0.000 description 2
- MLIWQXBKMZNZNF-KUHOPJCQSA-N (2e)-2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CC(=CC=2)N=[N+]=[N-])CC(C)CC1=CC1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-KUHOPJCQSA-N 0.000 description 1
- KJGKVKNUHXSXOH-UHFFFAOYSA-N 3-heptyl-1-phenyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CCCCCCC)C(=O)CN1C1=CC=CC=C1 KJGKVKNUHXSXOH-UHFFFAOYSA-N 0.000 description 1
- 229940096437 Protein S Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 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 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance 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
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
- G03C1/835—Macromolecular substances therefor, e.g. mordants
-
- 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
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
-
- 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
- G03C7/3882—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 polymer or latex
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/924—Significant dispersive or manipulative operation or step in making or stabilizing colloid system
- Y10S516/928—Mixing combined with non-mixing operation or step, successively or simultaneously, e.g. heating, cooling, ph change, ageing, milling
Definitions
- an acid halide of carries a plurality, preferably three, of difiera coupler was reacted with a protein such as entially color-sensitized emulsions, one or more gelatin under conditions which produced a comor all of which contain color couplers, i.
- a still furour invention includes cellulose nitrate and In!- FFECE UNi'l STATES PATENT INCORiORATION 0F COUPLERS IN NONGELATHN EMULSIUNS John A. Leermakers and scheming S. Fierke, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey Application Gctober 2b, 1M0, Serial No. 353,012 in Great Britain December 29, 1939 7 Claims. (Cl. 95-7)
- This invention relates to color couplers and sectional view of a multi-layer photographic eleto color photographic elements containing them. ment made according to our invention.
- the invention relates to color pho- In Russell and Staufier U. S. Patent 2,282,001, tographic elements of the type in which a supgranted May 5, 1942, a method for the preparaport (which may be of transparent material such 5 tion of color forming compounds non-diffusing in as cellulose nitrate or cellulose acetate or of gelatin was described. According to the method cliificulty.
- Patent 2,110,491 silver halide in a hydrolyzed cellulose organicacid March 3 1939 ester of approximately to approximately
- the following examples which are illustrative 3 acy Content, a compound o gelatin and a only, indicate methods of forming emulsions accoupler capable of reacting with the development cording t our inventinn; product of aprimary aromatic amino coupl n Emmple 1 developing agent.
- Fig. 1 is a sec- A coupler-gelatin compound made as described tional view of asingle layer photographic element in Russell and Stauffer U. S. Patent 2,282,001,
- Fig. 2 is a comprising 10 grams of l-acetoxy-naphthalenethe vehicle.
- Example 2 An emulsion made as described in Example 1 was sensitized with 5-4-(3-ethyl-2(3)-benzothiazolylidene) -2-butenylidene-3 n heptyl 1 phenyl-2-thiohydantoin to produce red sensitivity. This emulsion was coated on a plate and dried. An emulsion was then placed in a similar manner by using as the coupler 2-cyano acetyl-naphthalene-x-sulfonyl gelatin, a magenta coupler.
- This emulsion was sensitized to green light with 5- (3-ethyl-2- (3) -benzolylidene) ethylidenel-S-n-heptyl 1 phenyI-Z-thiohydantoin.
- This emulsion was coated over the red sensitized emulsion and dried.
- This plate was then exposed under a step tablet to red light and to green light and to both green and red light together.
- the plate was then developed in the developer described in Example 1. Those areas exposed to red light produced a blue-green dye only, those areas exposed to green light yielded a magenta dye only and where mixtures of red light. and green light were used for exposure, a combination of blue-green and magenta dyes was produced.
- a blue-sensitive emulsion which need not be optically sensitized, and which would contain a yellow gelatin-coupler compound, could be coated over the emulsions described above to produce a complete multicolor element.
- Example 2 The preparation of the sensitizing dyes referred to in Example 2 is described in Brooker U. S. Patent 2,282,116, granted May 5, 1942.
- ID is a support of transparent material such as cellulose acetate or cellulose nitrate or opaque material such as paper, having thereon an emulsion layer ll of silver halide dispersed in a water permeable cellulose ester and containing particles l2 of a gelatin coupler compound.
- Fig. 2 shows a multi-layer element in which the support is coated with emulsion layers l3, l4 and I5 of silver halide dispersed in a water permeable cellulose ester and sensitive, respectively. to the red, green and blue regions of the spectrum.
- the element will contain the usual yellow filter layer l6 between layers l4 and I5. Layer l3 of this element.
- This element may be developed to a colored image directly after exposure or may be developed first in a black and white developer, then developed in a color forming developer to produce colored images in the remaining silver halide of the element.
- filter and antihalation layers may also be formed according to our invention by incorporating reaction products of dyes and gelatin in cellulose esters.
- the method of preparing a color-forming photographic emulsion which .comprises mixing with an emulsion of silver halide in a hydrolyzed cellulose organic acid ester of approximately 19% to approximately 33% acyl content; a compound of gelatin and a coupler capable of gelling and also capable of reacting with the development product of a primary aromatic amino coupling developing agent.
- the method of preparing a color-forming photographic emulsion which comprises mixing with an emulsion of silver halide in a hydrolyzed cellulose acetate of approximately 19% to approximately 33% acetyl content, a compound of gelatin and a coupler capable of elling and also capable of reacting with the development product of a primary aromatic amino coupling developing agent.
- the method of preparing a color-forming photographic emulsion which comprises mixing with an emulsion of silver halide in a hydrolyzed cellulose acetate propionate of approximately 19% to approximately 33% acyl content, a compound of gelatin and a coupler capable of gelling and also capable of reacting with the development product of a primary aromatic amino coupling developing agent.
- the method of preparing a color-forming photographic emulsion which comprises mixing with an emulsion of silver halide in a hydrolyzed cellulose organic acid ester of approximately 19% to approximately 33% acyl content, a naphthalene sulfonyl gelatin coupler capable of gelling and also capable of reacting with the development product of a primary aromatic amino coupling developing agent.
- a photographic emulsion capable of producing a colored image upon development in a primary aromatic amino coupling developing agent. which comprises a hydrolyzed cellulose organic acid ester of approximately 19% to approximately 33% acyl content containing a sensitive silver halide and a compound of gelatin and a coupler capable of gelling and also capable of reacting with said developing agent.
- a photographic emulsion capable of pro ducing a colored image upon development in a primary aromatic amino coupling developing agent which comprises a hydrolyzed cellulose acetate of approximately 19% to approximately 33% acetyl content containing a sensitive silver halide and a. compound of gelatin and a coupler capable of gelling and also capable of reacting v with said developing agent.
- a photographic emulsion capable of producing a. colored image upon development in a primary aromatic amino coupling developing agent,-
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Description
J. A. LEERMAKERS ETAL Filed 001:. 26, 1940 INCORPORATION OF COUPLERS IN NON-GELATIN EMULSIONS GELATl/l-COUPLER COMPOUND. \CELLULOSE EJTER EMUL5 -suPPo/eT.
5 LUE SENS/T/VE CELLULOSE ESTER EMULS/ON. YELLOW F/LTER.
GEL A-T/N- C OUPL E R COMPOUND.
6EL/4T//Y- COUPLER COMPOUND GREEN SENS/T/I/E CELLULOSE ESTER EMULSION. GELAT/N-COUPLER COMPOUND.
sup/ eer.
RED SENS/ T/VE CELL ULOSE ESTER EMULSION JQHNA. LEERMAKERS \5cHEw2/Ne 5.
lEAKE INVENTORS BY mafia /1 TTORNE YS opaque or translucent material such as paper) described in that application, an acid halide of carries a plurality, preferably three, of difiera coupler was reacted with a protein such as entially color-sensitized emulsions, one or more gelatin under conditions which produced a comor all of which contain color couplers, i. e., bodies pound of the protein and the coupler capable of which are capable of combining with the oxidaielline- This method involve th use f such tion product of the developing agent used for reaction conditions, for example, time and temdeveloping the exposed silver salt to metallic silperature f r a n, t at t p n s t ver with the production of coloring matter in the r app e b degraded and ed W t region where the silver is developed. Subsequent pier t pr du a mp und f th up r and removal of metallic silver without removal of the p te n which wo d je d which Co d be coloring matter leaves substantially clear transmixed with gelatin emulsions to form an emulsion parent dye images. capable of rendering a colored image upon suit- It is known that in materials of this kind able developmentare cast in layers such as one upon another, or particular in emulsions of silver halide in certain where they are dispersed in the form of differce u ose e The eomilollmlsi When S0 disentially color-sensitized grains in a single body persed, have still less tendency to wander from of a binder such as gelatin. Attempts have been the emulsion in which they a e orporated than made to avoid this difiiculty by introducing a in the case of gelatin emulsions. The physical group into the molecules of the couplers designed dissimilarity between gelatin and cellulose esters to .render them non-difiusing, either by increasis a distinct advantageas regardsthe wandering ofing'the molecular weight or by giving them some compounds of the former from layer to layer in degree of substantivity to the gelatin. multi-layer coatings of the layer. The chemical It is therefore, an object of the present indifficulties between the gelatin and the cellulose vention, to provide a method for incorporating ester is also an improvement over dispersions of couplers in silver halide emulsions. A further a gelatin compound in gelatin. 1 object is to provide a method for incorporating The dispersing medium suitable for use with couplers in non-gelatin emulsions. A still furour invention includes cellulose nitrate and In!- FFECE UNi'l STATES PATENT INCORiORATION 0F COUPLERS IN NONGELATHN EMULSIUNS John A. Leermakers and scheming S. Fierke, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey Application Gctober 2b, 1M0, Serial No. 353,012 in Great Britain December 29, 1939 7 Claims. (Cl. 95-7) This invention relates to color couplers and sectional view of a multi-layer photographic eleto color photographic elements containing them. ment made according to our invention.
In particular the invention relates to color pho- In Russell and Staufier U. S. Patent 2,282,001, tographic elements of the type in which a supgranted May 5, 1942, a method for the preparaport (which may be of transparent material such 5 tion of color forming compounds non-diffusing in as cellulose nitrate or cellulose acetate or of gelatin was described. According to the method cliificulty. arises from the fact that the couplers 20 It h s now been found that color formers tend to wander from the emulsions with which which have been combined W t t n o ot they are incorporated into the adjacent emulsion protein s described in Russe and Staufier Patwhereby the true color rendered is detrimentally ent 2,282,001, can be dispersed in emulsions of affected. This is the case where the emulsions silver halide in vehicles other than gelatin and in ther object is to provide a method for incordrolyzed cellulose organic acid esters of approxiporating couplers in non-gelatin emulsions so mately 19% to approximately 33% acyl content.
that they will not difiuse in multi-layer coat- Hydrolyzed esters having an acyl content of from ings. Other objects will appear from the fol- 19% t 2 are particularly s f l due to their lowin d script n of our inventionhigh water permeability.- A method for prepar- These objects are accomplished by mixing with ing dispersions of silver halide in esters of this a non-gelatin emulsion such as an emulsion of type is described in Salo U. S. Patent 2,110,491, silver halide in a hydrolyzed cellulose organicacid March 3 1939 ester of approximately to approximately The following examples, which are illustrative 3 acy Content, a compound o gelatin and a only, indicate methods of forming emulsions accoupler capable of reacting with the development cording t our inventinn; product of aprimary aromatic amino coupl n Emmple 1 developing agent.
In the accompanying drawing, Fig. 1 is a sec- A coupler-gelatin compound made as described tional view of asingle layer photographic element in Russell and Stauffer U. S. Patent 2,282,001,
made according to our invention and Fig. 2 is a comprising 10 grams of l-acetoxy-naphthalenethe vehicle.
-su1fjonyl gelatin was placed in 300 cc. of cold distilled water for four hours. The water was then drained off and the gelatin coupler was melted on a steam bath to produce 160 cc. of solution. When a portion of this solution was treated with a portion of the following developer and a small amount of potassium periodate, a deep blue-green color was produced showing that the coupler was capable of forming a colored image upon treatment. with the oxidation product of a coupling developer.
2-amino 5 diethylamino toluene hydrochloride grams 2.0 Sodium sulfite do 2.0 Sodium carbonate do 20.0 Potassium bromide do 2.0 Water cubic centimeters 1000.0
80 cc. of the gelatin-coupler solution, containing 5 grams of the gelatin-coupler compound, were aded to 95 cc. of a silver bromide emulsion in which cellulose acetate propionate having an acyl content of about 20% was used as This emulsion contained approximately 2% grams of silver bromide. A plate was coated with the emulsion coating the dispersed gelatin coupler and, after drying and exposure, were developed in the developing solution described above. A blue-green image was produced.
Example 2 An emulsion made as described in Example 1 was sensitized with 5-4-(3-ethyl-2(3)-benzothiazolylidene) -2-butenylidene-3 n heptyl 1 phenyl-2-thiohydantoin to produce red sensitivity. This emulsion was coated on a plate and dried. An emulsion was then placed in a similar manner by using as the coupler 2-cyano acetyl-naphthalene-x-sulfonyl gelatin, a magenta coupler. This emulsion was sensitized to green light with 5- (3-ethyl-2- (3) -benzolylidene) ethylidenel-S-n-heptyl 1 phenyI-Z-thiohydantoin. This emulsion was coated over the red sensitized emulsion and dried. This plate was then exposed under a step tablet to red light and to green light and to both green and red light together. The plate was then developed in the developer described in Example 1. Those areas exposed to red light produced a blue-green dye only, those areas exposed to green light yielded a magenta dye only and where mixtures of red light. and green light were used for exposure, a combination of blue-green and magenta dyes was produced. Similarly a blue-sensitive emulsion, which need not be optically sensitized, and which would contain a yellow gelatin-coupler compound, could be coated over the emulsions described above to produce a complete multicolor element.
The preparation of the sensitizing dyes referred to in Example 2 is described in Brooker U. S. Patent 2,282,116, granted May 5, 1942.
Our invention will now be described by reference to the accompanying drawing. As shown in Fig. 1, ID is a support of transparent material such as cellulose acetate or cellulose nitrate or opaque material such as paper, having thereon an emulsion layer ll of silver halide dispersed in a water permeable cellulose ester and containing particles l2 of a gelatin coupler compound. Fig. 2 shows a multi-layer element in which the support is coated with emulsion layers l3, l4 and I5 of silver halide dispersed in a water permeable cellulose ester and sensitive, respectively. to the red, green and blue regions of the spectrum. The element will contain the usual yellow filter layer l6 between layers l4 and I5. Layer l3 of this element. contains particles ll of gelatin and blue-green coupler, layer I4 contains particles I8 of gelatin and magenta coupler and layer 15 contains particles l9'oi gelatin and yellow coupler. This element may be developed to a colored image directly after exposure or may be developed first in a black and white developer, then developed in a color forming developer to produce colored images in the remaining silver halide of the element.
In addition to the formation of sensitive emulsions by incorporation of couplers in dispersions of silver halide in cellulose esters, filter and antihalation layers may also be formed according to our invention by incorporating reaction products of dyes and gelatin in cellulose esters.
The examples referred to herein are understood to be for purposes of illustration only and our invention is to be taken limited only by the scope of the appended claims.
We claim:
1. The method of preparing a color-forming photographic emulsion which .comprises mixing with an emulsion of silver halide in a hydrolyzed cellulose organic acid ester of approximately 19% to approximately 33% acyl content; a compound of gelatin and a coupler capable of gelling and also capable of reacting with the development product of a primary aromatic amino coupling developing agent.
2. The method of preparing a color-forming photographic emulsion which comprises mixing with an emulsion of silver halide in a hydrolyzed cellulose acetate of approximately 19% to approximately 33% acetyl content, a compound of gelatin and a coupler capable of elling and also capable of reacting with the development product of a primary aromatic amino coupling developing agent.
3. The method of preparing a color-forming photographic emulsion which comprises mixing with an emulsion of silver halide in a hydrolyzed cellulose acetate propionate of approximately 19% to approximately 33% acyl content, a compound of gelatin and a coupler capable of gelling and also capable of reacting with the development product of a primary aromatic amino coupling developing agent. g
4. The method of preparing a color-forming photographic emulsion which comprises mixing with an emulsion of silver halide in a hydrolyzed cellulose organic acid ester of approximately 19% to approximately 33% acyl content, a naphthalene sulfonyl gelatin coupler capable of gelling and also capable of reacting with the development product of a primary aromatic amino coupling developing agent.
5. A photographic emulsion capable of producing a colored image upon development in a primary aromatic amino coupling developing agent. which comprises a hydrolyzed cellulose organic acid ester of approximately 19% to approximately 33% acyl content containing a sensitive silver halide and a compound of gelatin and a coupler capable of gelling and also capable of reacting with said developing agent.
6. A photographic emulsion capable of pro ducing a colored image upon development in a primary aromatic amino coupling developing agent, which comprises a hydrolyzed cellulose acetate of approximately 19% to approximately 33% acetyl content containing a sensitive silver halide and a. compound of gelatin and a coupler capable of gelling and also capable of reacting v with said developing agent.
7. A photographic emulsion capable of producing a. colored image upon development in a primary aromatic amino coupling developing agent,-
which comprises a hydrolyzed cellulose acetate 5 reacting with said developing agent.
JOHN A. LEERMAKERS. SCHEURING S. FIERKE.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB236780X | 1939-01-23 | ||
| GB281239X | 1939-12-28 | ||
| GB291239X | 1939-12-29 | ||
| GB190140X | 1940-01-19 | ||
| GB230240X | 1940-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2318788A true US2318788A (en) | 1943-05-11 |
Family
ID=27516200
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US314689A Expired - Lifetime US2304940A (en) | 1939-01-23 | 1940-01-19 | Color photography |
| US363012A Expired - Lifetime US2318788A (en) | 1939-01-23 | 1940-10-26 | Incorporation of couplers in nongelatin emulsions |
| US371650A Expired - Lifetime US2279406A (en) | 1939-01-23 | 1940-12-26 | Color process using cellulose ester emulsions |
| US371776A Expired - Lifetime US2311020A (en) | 1939-01-23 | 1940-12-26 | Method of dispersing coloring materials in water swellable colloids |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US314689A Expired - Lifetime US2304940A (en) | 1939-01-23 | 1940-01-19 | Color photography |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US371650A Expired - Lifetime US2279406A (en) | 1939-01-23 | 1940-12-26 | Color process using cellulose ester emulsions |
| US371776A Expired - Lifetime US2311020A (en) | 1939-01-23 | 1940-12-26 | Method of dispersing coloring materials in water swellable colloids |
Country Status (6)
| Country | Link |
|---|---|
| US (4) | US2304940A (en) |
| BE (1) | BE440854A (en) |
| CH (1) | CH236780A (en) |
| FR (3) | FR51566E (en) |
| GB (2) | GB540525A (en) |
| NL (2) | NL63641C (en) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2415382A (en) * | 1944-03-31 | 1947-02-04 | Du Pont | Photographic elements including hydrophilic color formers |
| US2454043A (en) * | 1944-04-04 | 1948-11-16 | Ilford Ltd | Gelatino-silver halide photographic elements containing higher fatty alcohols |
| US2527267A (en) * | 1944-10-30 | 1950-10-24 | Ilford Ltd | Photographic layers containing gelatin-sulfonic acid complexes, and their preparation |
| US2527268A (en) * | 1944-10-30 | 1950-10-24 | Ilford Ltd | Production of photographic emulsions |
| GB585758A (en) * | 1944-10-30 | 1947-02-24 | John Alfred Henry Hart | Improvements in or relating to the production of photographic emulsions |
| US2527262A (en) * | 1944-10-30 | 1950-10-24 | Ilford Ltd | Photographic layers containing gelatin-anion soap complexes and their preparation |
| US2576850A (en) * | 1945-04-26 | 1951-11-27 | Du Pont | Gelling of polymeric compounds |
| US2428208A (en) * | 1945-06-20 | 1947-09-30 | Eastman Kodak Co | Dichromate bleach bath containing a wetting agent and method of bleaching therewith |
| US2478400A (en) * | 1945-08-17 | 1949-08-09 | Eastman Kodak Co | Silver halide photographic emulsion with developer and color coupler dispersed therein |
| US2534654A (en) * | 1946-01-11 | 1950-12-19 | Polaroid Corp | Ultraviolet absorbing filter |
| US2528496A (en) * | 1946-04-30 | 1950-11-07 | Chalkley Lyman | Photosensitive leucocyanide composition |
| US2571725A (en) * | 1946-08-15 | 1951-10-16 | Eastman Kodak Co | Eliminating stain in photographic color material |
| US2577127A (en) * | 1946-11-23 | 1951-12-04 | Du Pont | Photographic element with colloid layer containing color former and nonionic wettingagent |
| US2565418A (en) * | 1947-08-13 | 1951-08-21 | Eastman Kodak Co | Method of preparing photographic silver halide emulsions |
| BE484580A (en) * | 1947-08-29 | |||
| BE528163A (en) * | 1953-04-17 | |||
| BE543744A (en) * | 1954-12-20 | |||
| US2843489A (en) * | 1955-07-29 | 1958-07-15 | Eastman Kodak Co | Mixed packet photographic emulsions with polyvinyl resin continuous phase |
| BE551312A (en) * | 1955-10-01 | |||
| US2870012A (en) * | 1955-12-23 | 1959-01-20 | Eastman Kodak Co | Microdispersions of photographic color couplers |
| GB852922A (en) * | 1957-09-04 | 1960-11-02 | Gen Aniline & Film Corp | Color formers containing a m-alkylphenoxyacyl group |
| GB864060A (en) * | 1957-11-01 | 1961-03-29 | Gen Aniline & Film Corp | Mixed grain photographic emulsions |
| US3033680A (en) * | 1958-01-13 | 1962-05-08 | Eastman Kodak Co | Plasticized gelating compositions |
| CA684233A (en) * | 1959-05-25 | 1964-04-14 | C. Haas Howard | Photographic products and processes |
| JPS5448538A (en) * | 1977-09-12 | 1979-04-17 | Konishiroku Photo Ind Co Ltd | Color photographic material |
| JPS55129136A (en) * | 1979-03-27 | 1980-10-06 | Fuji Photo Film Co Ltd | Emulsifying method |
| JPS56126830A (en) * | 1980-03-11 | 1981-10-05 | Konishiroku Photo Ind Co Ltd | Silver halide photographic sensitive material |
| IT1197427B (en) * | 1982-05-14 | 1988-11-30 | Gian Franco Menicucci | METHOD FORMULATION METHOD FOR DENTAL AND COMPLEX USE OF ALLOYS SO OBTAINED |
| US4725529A (en) | 1985-04-30 | 1988-02-16 | Konishiroku Photo Industry Co., Ltd. | Developing inhibitor arrangment in light-sensitive silver halide color photographic materials |
| CA1303412C (en) | 1985-05-31 | 1992-06-16 | Shigeharu Koboshi | Method for forming direct positive color image |
| AU591540B2 (en) | 1985-12-28 | 1989-12-07 | Konishiroku Photo Industry Co., Ltd. | Method of processing light-sensitive silver halide color photographic material |
| US5700608A (en) * | 1995-07-31 | 1997-12-23 | Eastman Kodak Company | Process for making photographic emulsions and photographic elements and emulsions containing latent image forming units internally containing sensitizing dye |
-
0
- NL NL65241D patent/NL65241C/xx active
- BE BE440854D patent/BE440854A/xx unknown
- NL NL63641D patent/NL63641C/xx active
-
1939
- 1939-12-29 GB GB5549/41A patent/GB540525A/en not_active Expired
- 1939-12-29 GB GB33070/39A patent/GB540368A/en not_active Expired
-
1940
- 1940-01-19 US US314689A patent/US2304940A/en not_active Expired - Lifetime
- 1940-05-06 CH CH236780D patent/CH236780A/en unknown
- 1940-08-10 FR FR51566D patent/FR51566E/en not_active Expired
- 1940-10-26 US US363012A patent/US2318788A/en not_active Expired - Lifetime
- 1940-12-26 US US371650A patent/US2279406A/en not_active Expired - Lifetime
- 1940-12-26 US US371776A patent/US2311020A/en not_active Expired - Lifetime
-
1946
- 1946-09-30 FR FR951528D patent/FR951528A/en not_active Expired
- 1946-09-30 FR FR57149D patent/FR57149E/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US2279406A (en) | 1942-04-14 |
| FR51566E (en) | 1943-02-05 |
| NL63641C (en) | |
| GB540368A (en) | 1941-10-15 |
| NL65241C (en) | |
| CH236780A (en) | 1945-03-15 |
| FR951528A (en) | 1949-10-27 |
| US2304940A (en) | 1942-12-15 |
| FR57149E (en) | 1952-12-15 |
| BE440854A (en) | |
| GB540525A (en) | 1941-10-20 |
| US2311020A (en) | 1943-02-16 |
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