US2148979A - Color photography - Google Patents

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US2148979A
US2148979A US145066A US14506637A US2148979A US 2148979 A US2148979 A US 2148979A US 145066 A US145066 A US 145066A US 14506637 A US14506637 A US 14506637A US 2148979 A US2148979 A US 2148979A
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color
silver halide
halide emulsion
former
kilo
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Expired - Lifetime
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US145066A
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Dieterle Walter
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GAF Chemicals Corp
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Agfa Ansco Corp
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/26—Silver halide emulsions for subtractive colour processes
    • 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
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes

Definitions

  • the present invention relates to color photography and more particularly to the sensitizing oi multi-layer material for color development.
  • One of its objects is to provide a durable silver 5 halide emulsion layer containing color formers andhighly sensitive to red and to yellow green.
  • a further object is to provide a layer the sensitivity of which is sumcient both for the negative and the reversal process.
  • the present invention is based Von the observation that for sensitizing multi-layer silver halide emulsions suitable for color photography Il not all sensitizers used for ordinary black andwhite photography are operative. This is due to the fact that the sensitivity of a great many sensitizers is considerably depressed by the colorforming component contained in the layer.
  • the invention consists in sensitizing to red a '25 layer containing a color former for the bluegreen picture by addition of a sensitizer from the class of the dialkylaminothio, dialkylaminoselenoand dialkylaminoindocarbocyanines, and sensitizing to yellow-green a layer containing 30 a color former for the purple picture by addition of a dystui .from the class of fthe vsymmetrical 19.5'naphthoxocarbocyanines or unsymmetrical carbocyanines which contain a thiazoline ring or an azoie, benzoxazole, benzthiazoleor benz- 35 selenaz'ole-ring with further radicals in the benzene ring.
  • the substituents may be alkyl, halogen, benzoylamino or hydroaromatic groups (for example cyclohexyl); moreover, instead of one or both benzene rings, naphthalene rings and their o tetra-hydrogenated derivatives may be connected in the three possiblepositions with the ring containing nitrogen.
  • the dyestuis used for sensitizing the red-sensitive layer are described in U. S. patent application Ser. No. 591,389 namelyd Febru- 45 ary 0, 1932, and also in the German specification o. 606,699; in U. S. Patent 2,020,636, U. S. Patents 2,066,966/67/68 and in French specications Nos. 42,245 (addition to 730,966) and v42,256 (addition to 734,200).
  • For'sensitizing the 50 yellow-green sensitive layer there may be used,
  • the middle car-g bination disclosed herein is the rst combina i tion of layers the sensitivity of which is sufficient for negative processes or reversal processes.
  • the invention is also applicable for producing single layers carrying color formers which serve for making component color pictures.
  • the layers may also contain other usual additions to emulsions, for example stabilizers.
  • a multi-layer material for color photography comprising a support, a red-sensitive silver halide emulsion layer containinga color-former for the blue-green picture and capable of forming a dyestuff selected from the group consisting of quinoneimine-, azomethineand azo-dyestuis, said layer containing further a sensitizing dye corresponding to the following general formula:
  • Y and Y1 stand for a member of the group consisting of R o,s,se, ⁇ o/
  • R stands for alkyl
  • X stands for an anion
  • U stands for a member oi the group consisting of the dialkylamino radical, alkyl, alkoxy, a fused-on benzene nucleus, a tetrahydrogenated benzene nucleus
  • a yellow-green sensitive silver halide emulsion layer containing a color former for the purple picture and capable of forming a dyestui selected from the group consisting of quinoneimine, azomethinen and azodyestui'fs, said layer containing further a sensitizing dye being a member of the group consisting of naphthoxocarbocyanines, unsymmetrical carbocyanines containing one thiazoline nucleus and dyes corresponding with the following general formula: a
  • Rl /Zi V and W being a member of the group consisting of alkyl, alkoxy, a fused-on benzene nucleus, a
  • a multi-layer material for color photography which comprises a support, a red-sensitive silver halide emulsion layer containing as a colorformer octodecy- 1 -hydroxy- 2-naphthoylamine and a dye corresponding to the following formula R being alkyl, X being an anion, and a yellow- 4green sensitive silver halide emulsion layer containing as a color-former l-(m-oleoyl-aminophenyl) -S-methyl--pyrazolone and a dye corresponding to the following formula H Hl wherein R stands for alkyl and X stands for an anion.
  • a multi-layer material for color photography comprising a support, a red-sensitive silver halide emulsion layer containing a naphtahol color-former and a dye corresponding to the i'ollowing general formula:
  • Y and Y1 stand for a member of the group consisting of R 0, S, Se, ⁇ C/
  • a yellow-green sensitive silver halide emulsion layer containing a pyrakzolone colorformer and a dye being a member of the group consisting of 13.13'-naphthoxocarbocyanines, un-
  • V and ,W being a member of the group consisting of alkyl, alkoxy, a fused-on benzene nucleus, a tetrahydrogenated. benzene nucleus, the benzoylamino radical and a hydroaromatic radical, X being an anion, Z1 being a. member of the group consisting of 0, S, and Se, and R1 being a member of the group consisting of H and alkyl.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)

Description

COLOR PHOTOGRAPHY Filed May 27, 1937 JEA/S/T/ZED LAVE/2 PPOE 7' www Petented Feb. 2s, 1939 UNITED STATES PATENT OFFICE COLOR PHOTOGRAPHY of New York Application May 27, 1937, Serial No. 145,066
Germany May 29, 1936 4 Claims.
The present invention relates to color photography and more particularly to the sensitizing oi multi-layer material for color development.
One of its objects is to provide a durable silver 5 halide emulsion layer containing color formers andhighly sensitive to red and to yellow green.
A further object is to provide a layer the sensitivity of which is sumcient both for the negative and the reversal process.
Further objects will be apparent from the detailed specication following hereafter.
.The present invention is based Von the observation that for sensitizing multi-layer silver halide emulsions suitable for color photography Il not all sensitizers used for ordinary black andwhite photography are operative. This is due to the fact that the sensitivity of a great many sensitizers is considerably depressed by the colorforming component contained in the layer. zo Reference is made to the accompanying selfexplanatory drawing which shows the photographic element according to the present inven- The invention consists in sensitizing to red a '25 layer containing a color former for the bluegreen picture by addition of a sensitizer from the class of the dialkylaminothio, dialkylaminoselenoand dialkylaminoindocarbocyanines, and sensitizing to yellow-green a layer containing 30 a color former for the purple picture by addition of a dystui .from the class of fthe vsymmetrical 19.5'naphthoxocarbocyanines or unsymmetrical carbocyanines which contain a thiazoline ring or an azoie, benzoxazole, benzthiazoleor benz- 35 selenaz'ole-ring with further radicals in the benzene ring. The substituents may be alkyl, halogen, benzoylamino or hydroaromatic groups (for example cyclohexyl); moreover, instead of one or both benzene rings, naphthalene rings and their o tetra-hydrogenated derivatives may be connected in the three possiblepositions with the ring containing nitrogen. The dyestuis used for sensitizing the red-sensitive layer are described in U. S. patent application Ser. No. 591,389 iiled Febru- 45 ary 0, 1932, and also in the German specification o. 606,699; in U. S. Patent 2,020,636, U. S. Patents 2,066,966/67/68 and in French specications Nos. 42,245 (addition to 730,966) and v42,256 (addition to 734,200). For'sensitizing the 50 yellow-green sensitive layer there may be used,
for example '-naphthoxocarbocyanine andits substitution products in which the middle car-g bination disclosed herein is the rst combina i tion of layers the sensitivity of which is sufficient for negative processes or reversal processes. Obviously .the invention is also applicable for producing single layers carrying color formers which serve for making component color pictures. In addition to the color formers and sensitzers, the layers may also contain other usual additions to emulsions, for example stabilizers.
The following examples when taken with the accompanying self-explanatory drawing disclosing a section of a lm according to the present invention illustrate the invention without limiting it to the specic details mentioned therein. 1. To 1 kilo of silver halide emulsion containing about per cent of gelatin and 6 per cent of silver halide are added 6 milligrams of the dyestuff paradiethylaminobenzthiocarbocyanine iodide and 5 grams of 1-hydroxy-2.4dibromo naphthalene dissolved in methanol.
Maximum sensitivity; 6500 Angstrom units; strong gap in the green.
2. To 1 kilo of silver halide emulsion are added 5 milligrams of the dyestuff para-dimethylaminobenzselenocarbocyanine iodide and 4 grams of ctodecyll-hydroxy-2-naphthoylamine.
Maximum sensitivity: about 6600 A. U.
3. To 1 kilo of silver halide emulsion containing about 10 per cent of gelatin and 6 per cent of silver halide are added 4 milligrams of the dyestui 6.6 diethylamino- 1.3.3.1' 3.3hexa meth'yiindocarbocyanine iodide and 5 grams of 1-hydroxy2;4dibromonaphthalene in the form of a solution in methanol.
Maximum sensitivity: about 6900 A. U.
4. To 1 kilo'of a silver halide emulsion which contains as color former for the purple picture 10 grams of 1- (meta-stearylamino) -pheny1-3- methyl--pyrazolone are added milligrams vof 1.1' diethylmesoethyl naphthoxocarbocyanine bromide.
Maximum sensitivity: 5650 A. U.
5. To 1 kilo of silver halide emulsion containing as color former for the purple picturey 4 grams of 1- (meta-oleyl-aminophenyl) -3-methyl-5-pyrazolone are 'added 8 milligrams of 1.1'-diethyl mesomethyltetrahydro 'naphthothio naphthoxocarbocyanine iodide.
Maximum sensitivity: 5600 A. U.
6. To 1 kilo of silver halide emulsion which tetrahydrogenated benzene nucleus, the benzoyicontains as color former for the purple picture 4 grams of 1-(meta-oleylaminophenyl) -3-methyl- -pyrazolone are added 16 milligrams of 1.1'diethyl-naphthothiothiazoline-carbocyanine iodide.
Maximum sensitivity: 5550 A. U.
7. To 1 kilo of silver halide emulsion are added 6 milligrams of para-diethylaminobenzthio--' naphthoxo-carbocyanine-ethyl iodide and 4 grams of octodecyl-1-hydroxy-2naphthoylamine.
Maximum sensitivity: 6100 A. U.
8. To 1 kilo of silver halide emulsion are added -6 milligrams of paradiethylaminobenzthio-S'.6'-
diethoxy-carbocyanine-ethyl iodide and 4 grams of octodecyl-1-hydroxy-2-naphthoylamine.
Maximum sensitivity: 6500 A. U.
9. To 1 kilo of silver halide emulsion which contains a color-former for the purple picture l0 grams of 1-stearyl-aminophenyl-3-methyl-5- pyrazolone are added 15 milligrams of 11di ethylmesomethyl (tetrahydro naphthothio) -naphthcxocarbocyanine iodide.
Maximum sensitivity: 5650 A. U.
10. To 1 kilo of silver halide emulsion are added 8 milligrams of l.l'-diethyl-para-diethylaminobenzthiometa-phenyloxocarbocyanine iodide and 4 grams of octodecyl-l-hydroxy-Z- naphthoylamine.
Maximum sensitivity: 6000 A. U.
What I claim is:
l. A multi-layer material for color photography comprising a support, a red-sensitive silver halide emulsion layer containinga color-former for the blue-green picture and capable of forming a dyestuff selected from the group consisting of quinoneimine-, azomethineand azo-dyestuis, said layer containing further a sensitizing dye corresponding to the following general formula:
wherein Y and Y1 stand for a member of the group consisting of R o,s,se,\o/
and R stands for alkyl, X stands for an anion, U stands for a member oi the group consisting of the dialkylamino radical, alkyl, alkoxy, a fused-on benzene nucleus, a tetrahydrogenated benzene nucleus; anda yellow-green sensitive silver halide emulsion layer containing a color former for the purple picture and capable of forming a dyestui selected from the group consisting of quinoneimine, azomethinen and azodyestui'fs, said layer containing further a sensitizing dye being a member of the group consisting of naphthoxocarbocyanines, unsymmetrical carbocyanines containing one thiazoline nucleus and dyes corresponding with the following general formula: a
Rl /Zi V and W being a member of the group consisting of alkyl, alkoxy, a fused-on benzene nucleus, a
former A and a. dye corresponding to thefollowing formula N n/ \C-cH=CH-cn=o/ oa i( \i n/ 1 n R being alkyl, X being an anion, a yellow-green sensitive silver halide'emulsion layer containing as a color-former i-(stearylaminophenyD-3- methyl-pyrazolone and a dye corresponding to the following formula R being alkyl, X being an anion.
3. A multi-layer material for color photography which comprises a support, a red-sensitive silver halide emulsion layer containing as a colorformer octodecy- 1 -hydroxy- 2-naphthoylamine and a dye corresponding to the following formula R being alkyl, X being an anion, and a yellow- 4green sensitive silver halide emulsion layer containing as a color-former l-(m-oleoyl-aminophenyl) -S-methyl--pyrazolone and a dye corresponding to the following formula H Hl wherein R stands for alkyl and X stands for an anion. I
4. A multi-layer material for color photography comprising a support, a red-sensitive silver halide emulsion layer containing a naphtahol color-former and a dye corresponding to the i'ollowing general formula:
wherein Y and Y1 stand for a member of the group consisting of R 0, S, Se,\C/
Inucleus; and a yellow-green sensitive silver halide emulsion layer, containing a pyrakzolone colorformer and a dye being a member of the group consisting of 13.13'-naphthoxocarbocyanines, un-
vsymmetrical carbocyanines containing one thiazoline nucleus and dyes corresponding to the i following general formula.
V and ,W being a member of the group consisting of alkyl, alkoxy, a fused-on benzene nucleus, a tetrahydrogenated. benzene nucleus, the benzoylamino radical and a hydroaromatic radical, X being an anion, Z1 being a. member of the group consisting of 0, S, and Se, and R1 being a member of the group consisting of H and alkyl.
WALTER DIETERLE.
US145066A 1936-05-29 1937-05-27 Color photography Expired - Lifetime US2148979A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2567712A (en) * 1945-06-07 1951-09-11 Du Pont Element for recording photographic images
US2640776A (en) * 1947-08-29 1953-06-02 Eastman Kodak Co Sensitized photographic emulsion containing color couplers
US2708625A (en) * 1951-01-19 1955-05-17 Gen Aniline & Film Corp Photographic element for the production of subtractive color images by sulfonhydrazide color development

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE971941C (en) * 1938-11-03 1959-04-16 Agfa Ag Process for the sensitization of halogenated silver emulsions containing dye-forming agents
DE972079C (en) * 1942-02-11 1959-05-21 Agfa Ag Process for the sensitization of halogenated silver emulsions containing dye-forming agents
DE968111C (en) * 1943-05-28 1958-01-16 Agfa Ag Fuer Photofabrikation Process for sensitizing halide silver emulsions

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE376781A (en) * 1930-03-19
GB354898A (en) * 1930-05-31 1931-08-20 Ici Ltd Improvements in and relating to the manufacture of photographic sensitisers
BE386129A (en) * 1931-02-07
DE630317C (en) * 1931-03-28 1936-05-26 I G Farbenindustrie Akt Ges Process for sensitizing halide silver emulsions
FR739866A (en) * 1931-07-11 1933-01-18 Ig Farbenindustrie Ag Process for the preparation of red light sensitive silver halide emulsions
DE625181C (en) * 1931-07-12 1936-02-10 I G Farbenindustrie Akt Ges Process for the red sensitization of photographic silver halide emulsions
BE395935A (en) * 1932-04-26
GB408596A (en) * 1932-10-06 1934-04-06 John Logie Baird Improvements in or relating to television apparatus or the like
GB415949A (en) * 1933-01-26 1934-09-06 Ig Farbenindustrie Ag Process for sensitising photographic silver halide emulsions
FR776597A (en) * 1933-08-08 1935-01-29 Ig Farbenindustrie Ag Process for producing orthochromatic emulsions

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2567712A (en) * 1945-06-07 1951-09-11 Du Pont Element for recording photographic images
US2640776A (en) * 1947-08-29 1953-06-02 Eastman Kodak Co Sensitized photographic emulsion containing color couplers
US2708625A (en) * 1951-01-19 1955-05-17 Gen Aniline & Film Corp Photographic element for the production of subtractive color images by sulfonhydrazide color development

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FR822436A (en) 1937-12-30
CH206204A (en) 1939-07-31
GB480778A (en) 1938-02-25
DE750122C (en) 1944-12-14
BE421721A (en) 1937-06-30

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