US2179238A - Manufacture of polychrome pictures - Google Patents
Manufacture of polychrome pictures Download PDFInfo
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- US2179238A US2179238A US72718A US7271836A US2179238A US 2179238 A US2179238 A US 2179238A US 72718 A US72718 A US 72718A US 7271836 A US7271836 A US 7271836A US 2179238 A US2179238 A US 2179238A
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- silver halide
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- PLXMOAALOJOTIY-FPTXNFDTSA-N Aesculin Natural products OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1Oc2cc3C=CC(=O)Oc3cc2O PLXMOAALOJOTIY-FPTXNFDTSA-N 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 5
- -1 silver halide Chemical class 0.000 description 30
- 239000000839 emulsion Substances 0.000 description 21
- 229910052709 silver Inorganic materials 0.000 description 20
- 239000004332 silver Substances 0.000 description 20
- 239000000463 material Substances 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- TXVWTOBHDDIASC-UHFFFAOYSA-N 1,2-diphenylethene-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)=C(N)C1=CC=CC=C1 TXVWTOBHDDIASC-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- BGNYDUHQASPIML-UHFFFAOYSA-N 2,4-diamino-3-benzamidobenzenesulfonic acid Chemical compound NC1=C(C(=C(C=C1)S(=O)(=O)O)N)NC(C1=CC=CC=C1)=O BGNYDUHQASPIML-UHFFFAOYSA-N 0.000 description 1
- GYVYGTTZKLHDON-UHFFFAOYSA-N 2-anilinophenol Chemical compound OC1=CC=CC=C1NC1=CC=CC=C1 GYVYGTTZKLHDON-UHFFFAOYSA-N 0.000 description 1
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 1
- IBUXIVGXQSMJEO-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxamide Chemical class C1=CC=C2C(C(=N)O)=C(O)C=CC2=C1 IBUXIVGXQSMJEO-UHFFFAOYSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- WPMIMQGUMDSIRM-UHFFFAOYSA-N 3,5-dianilinophenol Chemical compound C1(=CC=CC=C1)NC=1C=C(C=C(C1)NC1=CC=CC=C1)O WPMIMQGUMDSIRM-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- NOJXRHBIVBIMQY-UHFFFAOYSA-N 3-anilino-3-oxopropanoic acid Chemical compound OC(=O)CC(=O)NC1=CC=CC=C1 NOJXRHBIVBIMQY-UHFFFAOYSA-N 0.000 description 1
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 1
- WNRVXVWPXKDOEB-UHFFFAOYSA-N 4-methylpyrazol-3-one Chemical compound CC1=CN=NC1=O WNRVXVWPXKDOEB-UHFFFAOYSA-N 0.000 description 1
- ALLNAVCIMOJNMN-UHFFFAOYSA-N 4-phenylpyrazol-3-one Chemical compound O=C1N=NC=C1C1=CC=CC=C1 ALLNAVCIMOJNMN-UHFFFAOYSA-N 0.000 description 1
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical compound C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- OQENBJBTQPIZKA-UHFFFAOYSA-N chrysen-1-amine Chemical compound C1=CC2=C3C=CC=CC3=CC=C2C2=C1C(N)=CC=C2 OQENBJBTQPIZKA-UHFFFAOYSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000004060 quinone imines Chemical class 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- G03C7/32—Colour coupling substances
- G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific
Definitions
- Our present invention relates to the manufacture of polychrome pictures and more particularly to the manufacture of polychrome pictures from photographic silver halide emulsions.
- One of its objects is to provide a process for the production of improved polychrome pictures from silver halide emulsions.
- Another object are the improved photographic silver halide emulsion layers containing a component which produces color in the developer. Further objects will be seen from the detailed specification following hereafter.
- layers of silver halide emulsion can be developed in color by permitting the products of reaction, produced during the development from developer constituents which have a free amino-group, to condense with reactive phenols or amines to form quinone-imine dyestuifs ⁇ as for instance indoamines, lndoanllines, and indophenols.
- Dyestu formation also occurs with bodies which contain a reactive methylene group in which case azomethines are produced. Since, however, in the methods hitherto applied for development in color the component which produces color is incorporated in the developer the Vmethod leads merely to monochrome pictures.
- the substance that produces the color have failed, particularly when several layers are used one above the other for producing a polychrome picture.
- the components in the emulsion that produce color and are generally soluble in alkali pass into the adjacent layer into the developer.
- the present invention relates to a process in which such diiusion is prevented and the components are fixed in the several colloidal layers.
- the dyestuff component a group which lends the component substantive character with respect to the binding agent of the silver halide emulsion, that is to say, which prevents diffusion in the binding agent of the silver halide emulsion.
- the component can be dissolved in a water-soluble or alkalisoluble form in the colloid without fear that in the finished photographic material the component will diiuse into the adjacent layer or layers.
- the substantive character produced by introduction of the group can be further strengthened by means of an agent which has a precipitating action on or by means of a group which increases the molecular dimensions of the component.
- Agents which have a precipitating action are, for instance, diphenylguanidide and diphenylbiguanidide.
- Groups which increase the molecular dimensions of the component are, for instance, diphenylguanidide and diphenylbiguanidide. Groups
- Suitable groups for imparting such substantive character and therefore suitable for introduction into the hitherto known color-producers are, for example, diphenyl, dianlsidine, tolidine, diphenylcarboxylic acid, diamino-benzoylamino-diphenyl, stilbene, di-aminostilbene, diamino-benzoylaminostilbene, azoxybenzene, hydroxynaphthoic acid-amides, such as 2,3-hydroxynaphthoic acid and 4-(2,3)-hydroxynaphthoylamino-aniline, diaryl-ureas such as diamine-diphenylurea, diamino-benzoylamino-dlphenylurea, and
- amino-benzoylamino-o-sulfanilic acid benzthiazole, dehydrothiotolidine
- aminonaphthols such as 2-amino-5-naphthole-7sul ionic acid and 2-aminobenzoylamino--naphthole-'I-sulfonic acid, terephtaloylbisacetlc ester, 2,3-hydroXyanthracene-carboxylic acid, 2,3-hydroxycarbazole-carboxylic acid, aminochrysene, aminopyrene, and aminonaphthylene-oxide, or the like.
- Components for producing color into which these groups are to be introduced are,v for example, phenols such as m-aminophenol, o-o'- dinaphthole, o-hydroxydiphenyl, thymol, 2,5-d (phenylamino)phenol, aniline, naphthols, such as a-naphthol, a-hydroxynaphthoic acid, chloronaphthole and trichloronaphthole, naphthylamine, for instance, a-naphthylamine, aminonaphthols, for instance, 1,5-aminonaphthole, and all compounds which contain a reactive methylene group, for instance aceto-acetic esters, for instance, bromo-acetoacetic acid ester and acetoacetic anilide, cyano-acetic esters, for instance, cyanacetic acid ester, benzoyl-acetic esters, for instance, benzo
- diketohydrinden for instance, diketohydrinden, pyrazolones, such as phenylmethylpyrazolone and 1-phenyl-3 phenylpyrazolone, coumaranones, malonic acid anilide, w-cyanaceto-phenon, hydroxythionaphthene, and the like.
- three-color layers which may be arranged on one or both sides of the support, contain as components for producing color:
- methyl--pyrazolone for red development, 2.
- Terephthaloylbiacetic acid-anilide for yellow, 3, 3,5-di(phenylamino)phenol for blue-green.
- the alkali salts of these bodies dissolved in methanol, are stirred into a gelatin solution of 10 per cent strength in the proportion of 1 gram to 50 cc. of the gelatin solution, and the solution is then mixed with cc. of silver halide emulsion.
- a suitable developer is one consisting of 1 gram of diethylamino-anilide-hydrochloride, 6 grams of potassium carbonate and 100 cc. of water, to which sulilte may be added, if desired.
- the substantive groups may be introduced into the color components by means of an amide linkage.
- hydroxynaphthoic acid chloride may be condensed with 1-paminophenyl 3-methyl-5-pyrazolone so that an amide is formed by the carboxyl group of the hydroxynaphthoic acid and the amino group of the pyrazolone.
- the substantive groups may be introduced also by means of an ester linkage. It is again possible to directly connect the compounds.
- the single flgure of the accompanying drawing shows a film in accordance with the in- 'Vention having a support I coated with a silver halide emulsion layer 2 containing a color component having a group which imparts substantivity to the binding agent.
- a light-sensitive material for color photography comprising a silver halide emulsion containing a dyestui component for color forming development having attached thereto a group which lends said component substantive char- 'acter with respect to the binding agent of the silver halide emulsion and further containing a compound having a precipitating action on said dvestui component.
- a process of producing photographic ⁇ *color pictures which comprises treating an exposed photographic material having a silver halide emulsion containing a component for dyestuff forming development having attached thereto a group which lends said component substantive character with respect to the binding agent of the silver halide with a solution of a developing substance having an unsubstituted amino-group in order to produce the color.
- the step which comprises developing by means of an amino-developer an exposed photographic material having a silver halide emulsion containing a dyestui component for color forming development having attached thereto a group which renders said component fast to diiusion in the binding agent of the silver halide emulsion,.said group comprising at least two organic rings.
- the step which comprises developing by means of an amino-developer an exposed photographic material having a silver halide emulsion containing a dyestui component for color forming development having attached thereto a group which renders said component fast to diffusion in the binding agent of the silver halide emulsion, said group comprising at least ten carbon atoms.
- a light-sensitive material for color photography comprising a silver halide emulsion containing a mononuclear phenolic dyestuff component for color forming development having attached thereto a group which lends said component substantive character with respect to the binding agent of the silver halide emulsion, said group comprising at least two -membered aromatic rings.
- a light-sensitive material for color photography comprising a silver halide emulsion containing a dyestu component for color forming development, .selected from the class consisting of mononuclear phenolic dyestuff components and acyl acetic ester dyestui components, having attached thereto a group which renders said component fast to diffusion in the binding agent of the silver halide emulsion, said group comprising at least two G-membered aromatic rings.
Description
Nov. 7, 1939.
Filed April 4, 1956 tented Nov. 7, 1939 UNITED STATES t 2,ll9,238 PATENT FFICE MANUFACTURE 0F POLYCHROME PICTURES `Application April 4, 1936, Serial No. 72,718 In Germany April 10, 1935 10 Claims.
Our present invention relates to the manufacture of polychrome pictures and more particularly to the manufacture of polychrome pictures from photographic silver halide emulsions.
One of its objects is to provide a process for the production of improved polychrome pictures from silver halide emulsions. Another object are the improved photographic silver halide emulsion layers containing a component which produces color in the developer. Further objects will be seen from the detailed specification following hereafter.
It is known that layers of silver halide emulsion can be developed in color by permitting the products of reaction, produced during the development from developer constituents which have a free amino-group, to condense with reactive phenols or amines to form quinone-imine dyestuifs` as for instance indoamines, lndoanllines, and indophenols. Dyestu formation also occurs with bodies which contain a reactive methylene group in which case azomethines are produced. Since, however, in the methods hitherto applied for development in color the component which produces color is incorporated in the developer the Vmethod leads merely to monochrome pictures. Attempts to incorporate in the emulsion layer the substance that produces the color have failed, particularly when several layers are used one above the other for producing a polychrome picture. In this case either in` applying the second or a later layer to the first layer, or in bringing the material arranged in one or more layers into the developing solution, the components in the emulsion that produce color and are generally soluble in alkali, pass into the adjacent layer into the developer.
The present invention relates to a process in which such diiusion is prevented and the components are fixed in the several colloidal layers. For this purpose there is introduced into the dyestuff component a group which lends the component substantive character with respect to the binding agent of the silver halide emulsion, that is to say, which prevents diffusion in the binding agent of the silver halide emulsion. By introduction of such a group the component can be dissolved in a water-soluble or alkalisoluble form in the colloid without fear that in the finished photographic material the component will diiuse into the adjacent layer or layers. The substantive character produced by introduction of the group can be further strengthened by means of an agent which has a precipitating action on or by means of a group which increases the molecular dimensions of the component. Agents which have a precipitating action are, for instance, diphenylguanidide and diphenylbiguanidide. Groups which increase the molecular dimensions of the component are, for
(Cl. SI5-6) instance, amino groups, benzoyl groups and benzoyl amino groups which are introduced between t-he component which produces color and the component which imparts substantive character.
Suitable groups for imparting such substantive character and therefore suitable for introduction into the hitherto known color-producers are, for example, diphenyl, dianlsidine, tolidine, diphenylcarboxylic acid, diamino-benzoylamino-diphenyl, stilbene, di-aminostilbene, diamino-benzoylaminostilbene, azoxybenzene, hydroxynaphthoic acid-amides, such as 2,3-hydroxynaphthoic acid and 4-(2,3)-hydroxynaphthoylamino-aniline, diaryl-ureas such as diamine-diphenylurea, diamino-benzoylamino-dlphenylurea, and
the urea from amino-benzoylamino-o-sulfanilic acid, benzthiazole, dehydrothiotolidine, aminonaphthols, such as 2-amino-5-naphthole-7sul ionic acid and 2-aminobenzoylamino--naphthole-'I-sulfonic acid, terephtaloylbisacetlc ester, 2,3-hydroXyanthracene-carboxylic acid, 2,3-hydroxycarbazole-carboxylic acid, aminochrysene, aminopyrene, and aminonaphthylene-oxide, or the like. Components for producing color into which these groups are to be introduced are,v for example, phenols such as m-aminophenol, o-o'- dinaphthole, o-hydroxydiphenyl, thymol, 2,5-d (phenylamino)phenol, aniline, naphthols, such as a-naphthol, a-hydroxynaphthoic acid, chloronaphthole and trichloronaphthole, naphthylamine, for instance, a-naphthylamine, aminonaphthols, for instance, 1,5-aminonaphthole, and all compounds which contain a reactive methylene group, for instance aceto-acetic esters, for instance, bromo-acetoacetic acid ester and acetoacetic anilide, cyano-acetic esters, for instance, cyanacetic acid ester, benzoyl-acetic esters, for instance, benzoylacetic anidide, hydrindenes. for instance, diketohydrinden, pyrazolones, such as phenylmethylpyrazolone and 1-phenyl-3 phenylpyrazolone, coumaranones, malonic acid anilide, w-cyanaceto-phenon, hydroxythionaphthene, and the like.
The following example illustrates the invention:
'I'he three-color layers, which may be arranged on one or both sides of the support, contain as components for producing color:
methyl--pyrazolone for red development, 2. Terephthaloylbiacetic acid-anilide for yellow, 3, 3,5-di(phenylamino)phenol for blue-green.
The alkali salts of these bodies, dissolved in methanol, are stirred into a gelatin solution of 10 per cent strength in the proportion of 1 gram to 50 cc. of the gelatin solution, and the solution is then mixed with cc. of silver halide emulsion. A suitable developer is one consisting of 1 gram of diethylamino-anilide-hydrochloride, 6 grams of potassium carbonate and 100 cc. of water, to which sulilte may be added, if desired.
As it is shown in the example aforesaid, the substantive groups may be introduced into the color components by means of an amide linkage. Thus, for instance, hydroxynaphthoic acid chloride may be condensed with 1-paminophenyl 3-methyl-5-pyrazolone so that an amide is formed by the carboxyl group of the hydroxynaphthoic acid and the amino group of the pyrazolone. The substantive groups may be introduced also by means of an ester linkage. It is again possible to directly connect the compounds.
The single flgure of the accompanying drawing shows a film in accordance with the in- 'Vention having a support I coated with a silver halide emulsion layer 2 containing a color component having a group which imparts substantivity to the binding agent.
What we claim is:
1. A light-sensitive material for color photography comprising a silver halide emulsion containing a dyestui component for color forming development having attached thereto a group which lends said component substantive char- 'acter with respect to the binding agent of the silver halide emulsion and further containing a compound having a precipitating action on said dvestui component.
2. In a process of producing photographic `*color pictures the step which comprises treating an exposed photographic material having a silver halide emulsion containing a component for dyestuff forming development having attached thereto a group which lends said component substantive character with respect to the binding agent of the silver halide with a solution of a developing substance having an unsubstituted amino-group in order to produce the color.
3. In a process of producing photographic colored pictures, the step which comprises developing by means of an amino-developer an exposed photographic material having a silver halide emulsion containing a dyestui component for color forming development having attached thereto a group which renders said component fast to diiusion in the binding agent of the silver halide emulsion,.said group comprising at least two organic rings.
4. In a process of producing photographic co1- ored pictures, the step which comprises developing by means of an amino-developer an exposed photographic material having a silver halide emulsion containing a dyestui component for color forming development having attached thereto a group which renders said component fast to diffusion in the binding agent of the silver halide emulsion, said group comprising at least ten carbon atoms.
5. A light-sensitive material for color photography comprising a silver halide emulsion containing a mononuclear phenolic dyestuff component for color forming development having attached thereto a group which lends said component substantive character with respect to the binding agent of the silver halide emulsion, said group comprising at least two -membered aromatic rings.
6. The process as dened in claim 3. wherein at least 2 of said ringsare selected from the class consisting of fused rings and rings joined together by a linkage selected from the class consisting of a nuclear carbon to nuclear carbon linkage, an acid amide linkage, a -CH=CH- linkage, a -NON- linkage, and a -NHCONH- linkage.
7. 'I'he process as' defined in claim 3, wherein at least 1 of said rings is a heterocyclic ring.
8. A light-sensitive material for color photography comprising a silver halide emulsion containing a dyestu component for color forming development, .selected from the class consisting of mononuclear phenolic dyestuff components and acyl acetic ester dyestui components, having attached thereto a group which renders said component fast to diffusion in the binding agent of the silver halide emulsion, said group comprising at least two G-membered aromatic rings.
9. A light-sensitive material as defined in claim 8, wherein the component for color forming is an aceto acetic ester.
l0. A light-sensitive material as dened in claim 8, wherein the component for color development is a cyanaoetic ester.
GUSTAV WIIMANNS. WILHELM SCHNEIDER. ERNST BAUER.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI52094D DE746135C (en) | 1935-04-10 | 1935-04-10 | Process for the production of colored images in halogen silver emulsion layers by color development |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2179238A true US2179238A (en) | 1939-11-07 |
Family
ID=27211014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US72718A Expired - Lifetime US2179238A (en) | 1935-04-10 | 1936-04-04 | Manufacture of polychrome pictures |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2179238A (en) |
| BE (1) | BE414508A (en) |
| DE (1) | DE746135C (en) |
| ES (1) | ES141845A1 (en) |
| FR (1) | FR803566A (en) |
| GB (2) | GB458400A (en) |
| NL (1) | NL49147C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2545687A (en) * | 1947-04-30 | 1951-03-20 | Gen Aniline & Film Corp | N-substituted benzimidazoles |
| US2584349A (en) * | 1944-11-10 | 1952-02-05 | Gen Aniline & Film Corp | Color forming development with an aromatic primary amino developer and alpha-[4-sulfophenylazo]-aceto-acet-2-4-dichloroanilide |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE419447A (en) * | 1936-01-18 | |||
| DE950890C (en) * | 1936-10-28 | 1956-10-18 | Agfa Ag Fuer Photofabrikation | Ultraviolet absorbing filter layers on light-sensitive photographic layers for black and white and color photography |
| DE744264C (en) * | 1938-07-14 | 1944-01-13 | Ig Farbenindustrie Ag | Process for the production of color photographic images with the aid of non-diffusible dye formers |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE257160C (en) * | ||||
| DE253335C (en) * | 1912-02-06 | |||
| DE439206C (en) * | 1924-12-10 | 1927-01-06 | Johannes Herzog & Co Photochem | Process for influencing the light in photographic layers by means of dyes |
| BE354987A (en) * | 1927-10-18 | |||
| BE370307A (en) * | 1929-05-17 | |||
| BE394502A (en) * | 1930-02-18 | |||
| BE376782A (en) * | 1930-03-19 | |||
| GB376795A (en) * | 1930-03-19 | 1932-07-18 | Leopold Damrosch Mannes | Improvements in and relating to colour photography |
| BE376781A (en) * | 1930-03-19 | |||
| GB365531A (en) * | 1930-09-20 | 1932-01-20 | Ig Farbenindustrie Ag | Manufacture of azo-dyestuffs insoluble in water and intermediate products therefor |
| GB417936A (en) * | 1933-04-10 | 1934-10-10 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of carboxylic acid arylides |
-
0
- BE BE414508D patent/BE414508A/xx unknown
- NL NL49147D patent/NL49147C/xx active
-
1935
- 1935-04-10 DE DEI52094D patent/DE746135C/en not_active Expired
- 1935-04-13 GB GB11502/35A patent/GB458400A/en not_active Expired
-
1936
- 1936-03-19 FR FR803566D patent/FR803566A/en not_active Expired
- 1936-03-31 ES ES0141845A patent/ES141845A1/en not_active Expired
- 1936-04-04 US US72718A patent/US2179238A/en not_active Expired - Lifetime
- 1936-05-20 GB GB14292/36A patent/GB475191A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2584349A (en) * | 1944-11-10 | 1952-02-05 | Gen Aniline & Film Corp | Color forming development with an aromatic primary amino developer and alpha-[4-sulfophenylazo]-aceto-acet-2-4-dichloroanilide |
| US2545687A (en) * | 1947-04-30 | 1951-03-20 | Gen Aniline & Film Corp | N-substituted benzimidazoles |
Also Published As
| Publication number | Publication date |
|---|---|
| GB475191A (en) | 1937-11-16 |
| NL49147C (en) | |
| ES141845A1 (en) | 1936-06-16 |
| BE414508A (en) | |
| GB458400A (en) | 1936-12-14 |
| DE746135C (en) | 1944-06-05 |
| FR803566A (en) | 1936-10-03 |
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